Molecules

11 pages, 921 KiB

Open AccessArticle

Microwave-Assisted and Conventional Extractions of Volatile Compounds from Rosa x damascena Mill. Fresh Petals for Cosmetic Applications

by Carla Villa, Francesco Saverio Robustelli Della Cuna, Eleonora Russo, Mohammed Farhad Ibrahim, Elena Grignani and Stefania Preda

Molecules 2022, 27(12), 3963; https://doi.org/10.3390/molecules27123963 - 20 Jun 2022

Cited by 7 | Viewed by 2152

Abstract

Rosa x damascena Mill. essential oil is mainly used in the cosmetics and perfumery industry, but it also finds application in the food industry as a flavoring agent. The chemical composition of essential oils is affected by environment, soil, harvesting technique, storage condition, [...] Read more.

Rosa x damascena Mill. essential oil is mainly used in the cosmetics and perfumery industry, but it also finds application in the food industry as a flavoring agent. The chemical composition of essential oils is affected by environment, soil, harvesting technique, storage condition, and extraction methods. Nowadays, the study and design of greener, more efficient, and sustainable extractive procedures is the main and strategic focus in the chemical research and development of botanical derivatives, especially as regards fragrances and essential oils. Several technologies are available, and the best method to use depends on the desired chemicals, but conventional extractive processes are often laborious and time-consuming, involve large amounts of solvents, and may cause the partial loss of volatiles, affecting the quality of the final product. In the last decade, microwave irradiation has been successfully applied to classical techniques, often improving the general extractive efficiency and extract quality. In the present paper, as a preliminary analytical screening approach, two microwave-mediated techniques, Solvent-Free Microwave Extraction (SFME) and Microwave Hydrodiffusion and Gravity (MHG), and two conventional procedures, Hydrodistillation (HD) and Steam Distillation (SD), were applied and compared for the extraction of volatile compounds from R. x damascena fresh petals to highlight differences and advantages of the selected procedure and of the obtained extracts useful in a cosmetic context as fragrances or active ingredients. The chemical composition of the extracts was investigated by GC-MS and GC-FID. Sixty-one components, distributed in the four techniques, were identified. SD and HD are dominated by oxygenated terpenes (59.01% and 50.06%, respectively), while MHG and SFME extracts are dominated by alcohols (61.67% and 46.81%, respectively). A relevant variability in the composition of the extracts relating to the extraction techniques used was observed. To point out the correlation between the process and composition of the obtained natural products, principal component analysis (PCA) of the data extracted from GC-FID was used. Taking into account a cosmetic application, SFME shows several advantages when compared with the other procedures. The extract (obtained in a significantly higher amount) contains a meaningful lower level of potential fragrance allergenic compounds and quite a double amount of benzyl alcohol and 2-phenyl ethanol that can also enhance the preservative action in personal care products. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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17 pages, 6506 KiB

Open AccessArticle

Halogen-Based 17β-HSD1 Inhibitors: Insights from DFT, Docking, and Molecular Dynamics Simulation Studies

by Arulsamy Kulandaisamy, Murugesan Panneerselvam, Rajadurai Vijay Solomon, Madhavan Jaccob, Jaganathan Ramakrishnan, Kumaradhas Poomani, Muralikannan Maruthamuthu and Nagendran Tharmalingam

Molecules 2022, 27(12), 3962; https://doi.org/10.3390/molecules27123962 - 20 Jun 2022

Cited by 3 | Viewed by 2033

Abstract

The high expression of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) mRNA has been found in breast cancer tissues and endometriosis. The current research focuses on preparing a range of organic molecules as 17β-HSD1 inhibitors. Among them, the derivatives of hydroxyphenyl naphthol steroidomimetics are reported [...] Read more.

The high expression of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) mRNA has been found in breast cancer tissues and endometriosis. The current research focuses on preparing a range of organic molecules as 17β-HSD1 inhibitors. Among them, the derivatives of hydroxyphenyl naphthol steroidomimetics are reported as one of the potential groups of inhibitors for treating estrogen-dependent disorders. Looking at the recent trends in drug design, many halogen-based drugs have been approved by the FDA in the last few years. Here, we propose sixteen potential hydroxyphenyl naphthol steroidomimetics-based inhibitors through halogen substitution. Our Frontier Molecular Orbitals (FMO) analysis reveals that the halogen atom significantly lowers the Lowest Unoccupied Molecular Orbital (LUMO) level, and iodine shows an excellent capability to reduce the LUMO in particular. Tri-halogen substitution shows more chemical reactivity via a reduced HOMO–LUMO gap. Furthermore, the computed DFT descriptors highlight the structure–property relationship towards their binding ability to the 17β-HSD1 protein. We analyze the nature of different noncovalent interactions between these molecules and the 17β-HSD1 using molecular docking analysis. The halogen-derived molecules showed binding energy ranging from −10.26 to −11.94 kcal/mol. Furthermore, the molecular dynamics (MD) simulations show that the newly proposed compounds provide good stability with 17β-HSD1. The information obtained from this investigation will advance our knowledge of the 17β-HSD1 inhibitors and offer clues to developing new 17β-HSD1 inhibitors for future applications. Full article

(This article belongs to the Special Issue Simulational and Computational Approaches to Enhance Protein Inhibitor Designs)

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23 pages, 2665 KiB

Open AccessArticle

Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides

by Victoria Osipova, Yulia Gracheva, Maria Polovinkina, Daria Burmistrova and Nadezhda Berberova

Molecules 2022, 27(12), 3961; https://doi.org/10.3390/molecules27123961 - 20 Jun 2022

Cited by 8 | Viewed by 2064

Abstract

Natural or synthetic antioxidants with biomimetic fragments protect the functional and structural integrity of biological molecules at a minimum concentration, and may be used as potential chemotherapeutic agents. This paper is devoted to in silico and in vitro evaluation of the antioxidant and [...] Read more.

Natural or synthetic antioxidants with biomimetic fragments protect the functional and structural integrity of biological molecules at a minimum concentration, and may be used as potential chemotherapeutic agents. This paper is devoted to in silico and in vitro evaluation of the antioxidant and cytotoxic properties of synthetic analogues of natural compounds—aromatic oligosulfides. The antiradical and SOD-protective activity of oligosulfides was demonstrated in the reaction with O₂^–• generated in enzymatic and non-enzymatic systems. It was found that phenol-containing disulfides significantly reduced the accumulation level of hydroperoxides and secondary carbonyl thiobarbituric acid reactive substances, which are primary products of oleic acid peroxidation. The antioxidant efficiency of bis(3,5-di-tert-butyl-4-hydroxyphenyl) disulfide increased over time due to the synergistic action of the 2,6-di-tert-butylphenol fragment and the disulfide linker. The highest cytotoxicity on the A-549 and HCT-116 cell lines was found for bis(3,4-dimethoxyphenyl) disulfide. Significant induction of apoptosis in HCT-116 cells in the presence of bis(3,4-dimethoxyphenyl) disulfide indicates the prospect of its use as an antitumor agent. The significant and moderate dependences revealed between various types of activities of the studied aromatic oligosulfides can be used in the development of a strategy for the synthesis and study of target-oriented compounds with predictable biological activity. Full article

(This article belongs to the Special Issue Synthesis of Bioactive Compounds)

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16 pages, 3100 KiB

Open AccessArticle

Design, Synthesis and Cytotoxic Activity Evaluation of Newly Synthesized Amides-Based TMP Moiety as Potential Anticancer Agents over HepG2 Cells

by Tarfah Al-Warhi, Adil Aldhahrani, Fayez Althobaiti, Eman Fayad, Ola A. Abu Ali, Sarah Albogami, Ali H. Abu Almaaty, Amgad I. M. Khedr, Syed Nasir Abbas Bukhari and Islam Zaki

Molecules 2022, 27(12), 3960; https://doi.org/10.3390/molecules27123960 - 20 Jun 2022

Cited by 2 | Viewed by 1720

Abstract

A novel series of amides based TMP moiety was designed, synthesized and evaluated for their antiproliferative as well as enzyme inhibition activity. Compounds 6a and 6b showed remarkable cytotoxic activity against HepG2 cells with IC₅₀ values 0.65 and 0.92 μM, respectively compared [...] Read more.

A novel series of amides based TMP moiety was designed, synthesized and evaluated for their antiproliferative as well as enzyme inhibition activity. Compounds 6a and 6b showed remarkable cytotoxic activity against HepG2 cells with IC₅₀ values 0.65 and 0.92 μM, respectively compared with SAHA and CA-4 as reference compounds. In addition, compound 6a demonstrated good HDAC-tubulin dual inhibition activity as it showed better HDAC activity as well as anti-tubulin activity. Moreover, compound 6a exhibited G2/M phase arrest and pre-G1 apoptosis as demonstrated by cell cycle analysis and Annexin V assays. Further apoptosis studies demonstrated that compound 6a boosted the level of caspase 3/7. Caspase 3/7 activation and apoptosis induction were evidenced by decrease in mitochondrial permeability suggesting that activation of caspase 3/7 may occur via mitochondrial apoptotic pathway. Full article

(This article belongs to the Section Bioorganic Chemistry)

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12 pages, 984 KiB

Open AccessArticle

Trichoderma Enzymes for Degradation of Aflatoxin B1 and Ochratoxin A

by Irene Dini, Vittoria Alborino, Stefania Lanzuise, Nadia Lombardi, Roberta Marra, Anna Balestrieri, Alberto Ritieni, Sheridan L. Woo and Francesco Vinale

Molecules 2022, 27(12), 3959; https://doi.org/10.3390/molecules27123959 - 20 Jun 2022

Cited by 14 | Viewed by 2234

Abstract

The contamination of agricultural products with mycotoxins causes risks to animal and human health and severe economic losses. Mycotoxicoses can be reduced by preventing fungal infection using chemical and biological approaches. The chemical strategies can release toxic molecules; therefore, strategies for biological control [...] Read more.

The contamination of agricultural products with mycotoxins causes risks to animal and human health and severe economic losses. Mycotoxicoses can be reduced by preventing fungal infection using chemical and biological approaches. The chemical strategies can release toxic molecules; therefore, strategies for biological control are being evaluated, such as using nontoxic fungi and their metabolites. This work evaluated the effect of exoenzymes produced by the beneficial fungus Trichoderma afroharzianum strain T22 in degrading Aflatoxin B1 (AFB1) and Ochratoxin A (OTA). The ability of Trichoderma to produce hydrolases was stimulated by using different inducing substrates. The highest AFB1 and OTA degradation activity was obtained using a medium containing lyophilized mushrooms and crude fiber. The T. afroharzianum T22’s ability to reduce mycotoxins may be attributed to peroxidase enzymes. This study showed that T.afroharzianum strain T22 or its peroxidase supplementation could represent a sustainable strategy for the degradation of AFB1 and OTA in feed and food products. Full article

(This article belongs to the Special Issue Natural Secondary Metabolites II)

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14 pages, 3476 KiB

Open AccessArticle

A New Method for Calculating the Relative Permeability Curve of Polymer Flooding Based on the Viscosity Variation Law of Polymer Transporting in Porous Media

by Wenchao Jiang, Zhaowei Hou, Xiaolin Wu, Kaoping Song, Erlong Yang, Bin Huang, Chi Dong, Shouliang Lu, Liyan Sun, Jian Gai, Shichun Yao, Yunchao Wang, Chunlin Nie, Dengyu Yuan and Qinghua Xu

Molecules 2022, 27(12), 3958; https://doi.org/10.3390/molecules27123958 - 20 Jun 2022

Cited by 3 | Viewed by 1574

Abstract

Relative permeability of polymer flooding plays a very important role in oil field development. This paper aimed to measure and calculate the relative permeability curves of polymer flooding more accurately. First, viscosity variation law of polymer in porous media was studied. Rock particles [...] Read more.

Relative permeability of polymer flooding plays a very important role in oil field development. This paper aimed to measure and calculate the relative permeability curves of polymer flooding more accurately. First, viscosity variation law of polymer in porous media was studied. Rock particles of different diameters and cementing agent were used to make artificial cores and hydrophobically associating polymer solutions were prepared for experiments. Polymer solutions were injected into the cores filled with crude oil and irreducible water. In the process of polymer flooding, produced fluid was collected at different water saturations and locations of the core. Polymer solutions were separated and their viscosities were measured. With the experimental data, the viscosity variation rule of polymer transporting in porous media was explored. The result indicates that the viscosity retention rate of polymer solutions transporting in porous media has power function relationship with the water saturation and the dimensionless distance from the core inlet. Finally, the relative permeability curves of polymer flooding were measured by unsteady state method and the viscosity variation rule was applied to the calculation of the relative permeability curves. Full article

(This article belongs to the Special Issue Recent Advances in Polymer Flooding in China)

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13 pages, 4300 KiB

Open AccessArticle

Determination of 2-Acetyl-1-pyrroline via a Color-Change Reaction Using Chromium Hexacarbonyl

by Chonlada Bennett, Woraprapa Sriyotai, Sirakorn Wiratchan, Natthawat Semakul and Sugunya Mahatheeranont

Molecules 2022, 27(12), 3957; https://doi.org/10.3390/molecules27123957 - 20 Jun 2022

Cited by 3 | Viewed by 2110

Abstract

At present, there is no colorimetric method for the quantitation of the aroma compound 2-acetyl-1-pyrroline (2AP). A novel colorimetric method was developed for the determination of 2AP content using chromium hexacarbonyl (Cr(CO)₆) as a reagent. The reaction of synthetic 2AP with [...] Read more.

At present, there is no colorimetric method for the quantitation of the aroma compound 2-acetyl-1-pyrroline (2AP). A novel colorimetric method was developed for the determination of 2AP content using chromium hexacarbonyl (Cr(CO)₆) as a reagent. The reaction of synthetic 2AP with chromium hexacarbonyl reagent solution in the presence of light produced a green product with an absorption maximum (λ_max) at 623 nm. GC–MS was used to confirm the color-change reaction, which showed the loss of 2AP after the addition of Cr(CO)₆. This novel method enables facile and cost-effective determination of 2AP in fragrant rice. A comparative analysis of fragrant and nonfragrant rice grain extracts showed that no color-change reaction occurred with the nonfragrant rice sample. A limit of detection (LOD) of 2.00 mg L⁻¹ was determined by method validation with an effective linear concentration ranging from 5.00 to 60.00 mg L⁻¹ of 2AP. The results obtained using the developed colorimetric method were consistent with those obtained by automated static headspace gas chromatography with nitrogen-phosphorus detection (SHS-GC–NPD). Full article

(This article belongs to the Special Issue Analysis of Volatile and Odor Compounds in Foods—Second Edition)

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21 pages, 5351 KiB

Open AccessReview

The Role of Saponins in the Treatment of Neuropathic Pain

by Bei Tan, Xueqing Wu, Jie Yu and Zhong Chen

Molecules 2022, 27(12), 3956; https://doi.org/10.3390/molecules27123956 - 20 Jun 2022

Cited by 6 | Viewed by 2482

Abstract

Neuropathic pain is a chronic pain caused by tissue injury or disease involving the somatosensory nervous system, which seriously affects the patient’s body function and quality of life. At present, most clinical medications for the treatment of neuropathic pain, including antidepressants, antiepileptic drugs, [...] Read more.

Neuropathic pain is a chronic pain caused by tissue injury or disease involving the somatosensory nervous system, which seriously affects the patient’s body function and quality of life. At present, most clinical medications for the treatment of neuropathic pain, including antidepressants, antiepileptic drugs, or analgesics, often have limited efficacy and non-negligible side effects. As a bioactive and therapeutic component extracted from Chinese herbal medicine, the role of the effective compounds in the prevention and treatment of neuropathic pain have gradually become a research focus to explore new analgesics. Notably, saponins have shown analgesic effects in a large number of animal models. In this review, we summarized the most updated information of saponins, related to their analgesic effects in neuropathic pain, and the recent progress on the research of therapeutic targets and the potential mechanisms. Furthermore, we put up with some perspectives on future investigation to reveal the precise role of saponins in neuropathic pain. Full article

(This article belongs to the Special Issue Molecular Targets in Neuroscience and Neurotherapeutics)

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13 pages, 1910 KiB

Open AccessArticle

Preparation, Characterization, and In Vitro Anticancer Activity Evaluation of Broccoli-Derived Extracellular Vesicle-Coated Astaxanthin Nanoparticles

by Chunmei Li, Qi Song, Xialian Yin, Ruilong Song and Gang Chen

Molecules 2022, 27(12), 3955; https://doi.org/10.3390/molecules27123955 - 20 Jun 2022

Cited by 18 | Viewed by 2125

Abstract

Astaxanthin (AST) is a type of ketone carotenoid having significant antioxidation and anticancer abilities. However, its application is limited due to its low stability and bioavailability. In our study, poly (lactic-co-glycolic acid) (PLGA)-encapsulated AST (AST@PLGA) nanoparticles were prepared by emulsion solvent evaporation method [...] Read more.

Astaxanthin (AST) is a type of ketone carotenoid having significant antioxidation and anticancer abilities. However, its application is limited due to its low stability and bioavailability. In our study, poly (lactic-co-glycolic acid) (PLGA)-encapsulated AST (AST@PLGA) nanoparticles were prepared by emulsion solvent evaporation method and then further processed by ultrasound with broccoli-derived extracellular vesicles (BEVs), thereby evolving as BEV-coated AST@PLGA nanoparticles (AST@PLGA@BEVs). The preparation process and methods were optimized by three factors and three levels of response surface method to increase drug loading (DL). After optimization, the DL was increased to 6.824%, and the size, polydispersity index, and zeta potential of AST@PLGA@BEVs reached 191.60 ± 2.23 nm, 0.166, and −15.85 ± 0.92 mV, respectively. Moreover, AST@PLGA@BEVs exhibited more notable anticancer activity than AST in vitro. Collectively, these results indicate that the method of loading AST in broccoli-derived EVs is feasible and has important significance for the further development and utilization of AST as a functional food. Full article

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16 pages, 2995 KiB

Open AccessArticle

Quantification of Salicylates and Flavonoids in Poplar Bark and Leaves Based on IR, NIR, and Raman Spectra

by Sylwester Mazurek, Maciej Włodarczyk, Sonia Pielorz, Piotr Okińczyc, Piotr M. Kuś, Gabriela Długosz, Diana Vidal-Yañez and Roman Szostak

Molecules 2022, 27(12), 3954; https://doi.org/10.3390/molecules27123954 - 20 Jun 2022

Cited by 4 | Viewed by 1911

Abstract

Poplar bark and leaves can be an attractive source of salicylates and other biologically active compounds used in medicine. However, the biochemical variability of poplar material requires a standardization prior to processing. The official analytical protocols used in the pharmaceutical industry rely on [...] Read more.

Poplar bark and leaves can be an attractive source of salicylates and other biologically active compounds used in medicine. However, the biochemical variability of poplar material requires a standardization prior to processing. The official analytical protocols used in the pharmaceutical industry rely on the extraction of active compounds, which makes their determination long and costly. An analysis of plant materials in their native state can be performed using vibrational spectroscopy. This paper presents for the first time a comparison of diffuse reflectance in the near- and mid-infrared regions, attenuated total reflection, and Raman spectroscopy used for the simultaneous determination of salicylates and flavonoids in poplar bark and leaves. Based on 185 spectra of various poplar species and hybrid powdered samples, partial least squares regression models, characterized by the relative standard errors of prediction in the 4.5–9.9% range for both calibration and validation sets, were developed. These models allow for fast and precise quantification of the studied active compounds in poplar bark and leaves without any chemical sample treatment. Full article

(This article belongs to the Special Issue Chemometrics in Analytical Chemistry)

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11 pages, 1094 KiB

Open AccessCommunication

Exosomal MicroRNA as Biomarkers for Diagnosing or Monitoring the Progression of Ovarian Clear Cell Carcinoma: A Pilot Study

by Kayo Horie, Naoki Nanashima, Yoshihito Yokoyama, Haruhiko Yoshioka and Jun Watanabe

Molecules 2022, 27(12), 3953; https://doi.org/10.3390/molecules27123953 - 20 Jun 2022

Cited by 10 | Viewed by 2008

Abstract

Ovarian cancer is the most common cause of gynecological malignancy-related mortality since early-stage disease is difficult to diagnose. Advanced clear cell carcinoma of the ovary (CCCO) has dismal prognosis, and its incidence has been increasing in Japan, emphasizing the need for highly sensitive [...] Read more.

Ovarian cancer is the most common cause of gynecological malignancy-related mortality since early-stage disease is difficult to diagnose. Advanced clear cell carcinoma of the ovary (CCCO) has dismal prognosis, and its incidence has been increasing in Japan, emphasizing the need for highly sensitive diagnostic and prognostic CCCO biomarkers. Exosomal microRNAs (miRNAs) secreted by tumor cells are known to play a role in carcinogenesis; however, their involvement in ovarian cancer is unclear. In this study, we performed expression profiling of miRNAs from exosomes released by five cell lines representing different histological types of ovarian cancer. Exosomes isolated from culture media of cancer and normal cells were compared for miRNA composition using human miRNA microarray. We detected 143 exosomal miRNAs, whose expression was ≥1.5-fold higher in ovarian cancer cells than in the control. Among them, 28 miRNAs were upregulated in cells of all histological ovarian cancer types compared to control, and three were upregulated in CCCO cells compared to other types. Functional analyses indicated that miR-21 overexpressed in CCCO cells targeted tumor suppressor genes PTEN, TPM1, PDCD4, and MASP1. The identified miRNAs could represent novel candidate biomarkers to diagnose or monitor progression of ovarian cancer, particularly CCCO. Full article

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10 pages, 1308 KiB

Open AccessArticle

Wooden-Tip Electrospray Mass Spectrometry Characterization of Human Hemoglobin in Whole Blood Sample for Thalassemia Screening: A Pilot Study

by Tingting Huang, Ting Huang, Yongyi Zou, Kang Xie, Yinqin Shen, Wen Zhang, Shuhui Huang, Yanqiu Liu and Bicheng Yang

Molecules 2022, 27(12), 3952; https://doi.org/10.3390/molecules27123952 - 20 Jun 2022

Cited by 1 | Viewed by 1422

Abstract

Traditional analytical methods for thalassemia screening are needed to process complicated and time-consuming sample pretreatment. In recent decades, ambient mass spectrometry (MS) approaches have been proven to be an effective analytical strategy for direct sample analysis. In this work, we applied ambient MS [...] Read more.

Traditional analytical methods for thalassemia screening are needed to process complicated and time-consuming sample pretreatment. In recent decades, ambient mass spectrometry (MS) approaches have been proven to be an effective analytical strategy for direct sample analysis. In this work, we applied ambient MS with wooden-tip electrospray ionization (WT-ESI) for the direct analysis of raw human blood samples that were pre-identified by gene detection. A total of 319 whole blood samples were investigated in this work, including 100 α-thalassemia carriers, 67 β-thalassemia carriers, and 152 control healthy samples. Only one microliter of raw blood sample was directly loaded onto the surface of the wooden tip, and then five microliters of organic solvent and a high voltage of +3.0 kV were applied onto the wooden tip to generate spray ionization. Multiply charged ions of human hemoglobin (Hb) were directly observed by WT-ESI-MS from raw blood samples. The signal ratios of Hb chains were used to characterize two main types of thalassemia (α and β types) and healthy control blood samples. Our results suggested that the ratios of charged ions to Hb chains being at +13 would be an indicator for β-thalassemia screening. Full article

(This article belongs to the Special Issue Analytical Techniques in Pharmaceutical and Biomedical Analysis)

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12 pages, 1553 KiB

Open AccessArticle

Dielectric Properties Investigation of Metal–Insulator–Metal (MIM) Capacitors

by Li Xiong, Jin Hu, Zhao Yang, Xianglin Li, Hang Zhang and Guanhua Zhang

Molecules 2022, 27(12), 3951; https://doi.org/10.3390/molecules27123951 - 20 Jun 2022

Cited by 7 | Viewed by 3081

Abstract

This study presents the construction and dielectric properties investigation of atomic-layer-deposition Al₂O₃/TiO₂/HfO₂ dielectric-film-based metal–insulator–metal (MIM) capacitors. The influence of the dielectric layer material and thickness on the performance of MIM capacitors are also systematically investigated. The [...] Read more.

This study presents the construction and dielectric properties investigation of atomic-layer-deposition Al₂O₃/TiO₂/HfO₂ dielectric-film-based metal–insulator–metal (MIM) capacitors. The influence of the dielectric layer material and thickness on the performance of MIM capacitors are also systematically investigated. The morphology and surface roughness of dielectric films for different materials and thicknesses are analyzed via atomic force microscopy (AFM). Among them, the 25 nm Al₂O₃-based dielectric capacitor exhibits superior comprehensive electrical performance, including a high capacitance density of 7.89 fF·µm⁻², desirable breakdown voltage and leakage current of about 12 V and 1.4 × 10⁻¹⁰ A·cm⁻², and quadratic voltage coefficient of 303.6 ppm·V⁻². Simultaneously, the fabricated capacitor indicates desirable stability in terms of frequency and bias voltage (at 1 MHz), with the corresponding slight capacitance density variation of about 0.52 fF·µm⁻² and 0.25 fF·µm⁻². Furthermore, the mechanism of the variation in capacitance density and leakage current might be attributed to the Poole–Frenkel emission and charge-trapping effect of the high-k materials. All these results indicate potential applications in integrated passive devices. Full article

(This article belongs to the Special Issue Advanced Energy Storage Materials and Their Applications)

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22 pages, 2486 KiB

Open AccessArticle

Screening of Specific and Common Pathways in Breast Cancer Cell Lines MCF-7 and MDA-MB-231 Treated with Chlorophyllides Composites

by Keng-Shiang Huang, Yi-Ting Wang, Omkar Byadgi, Ting-Yu Huang, Mi-Hsueh Tai, Jei-Fu Shaw and Chih-Hui Yang

Molecules 2022, 27(12), 3950; https://doi.org/10.3390/molecules27123950 - 20 Jun 2022

Cited by 3 | Viewed by 2222

Abstract

Our previous findings have shown that the chlorophyllides composites have anticancer activities to breast cancer cell lines (MCF-7 and MDA-MB-231). In the present study, microarray gene expression profiling was utilized to investigate the chlorophyllides anticancer mechanism on the breast cancer cells lines. Results [...] Read more.

Our previous findings have shown that the chlorophyllides composites have anticancer activities to breast cancer cell lines (MCF-7 and MDA-MB-231). In the present study, microarray gene expression profiling was utilized to investigate the chlorophyllides anticancer mechanism on the breast cancer cells lines. Results showed that chlorophyllides composites induced upregulation of 43 and 56 differentially expressed genes (DEG) in MCF-7 and MDA-MB-231 cells, respectively. In both cell lines, chlorophyllides composites modulated the expression of annexin A4 (ANXA4), chemokine C-C motif receptor 1 (CCR1), stromal interaction molecule 2 (STIM2), ethanolamine kinase 1 (ETNK1) and member of RAS oncogene family (RAP2B). Further, the KEGG annotation revealed that chlorophyllides composites modulated DEGs that are associated with the endocrine system in MCF-7 cells and with the nervous system in MDA-MB-231 cells, respectively. The expression levels of 9 genes were validated by quantitative reverse transcription PCR (RT-qPCR). The expression of CCR1, STIM2, ETNK1, MAGl1 and TOP2A were upregulated in both chlorophyllides composites treated-MCF-7 and MDA-MB-231 cells. The different expression of NLRC5, SLC7A7 and PKN1 provided valuable information for future investigation and development of novel cancer therapy. Full article

(This article belongs to the Special Issue Metal-Based Drugs: Past, Present and Future)

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17 pages, 1769 KiB

Open AccessArticle

Influence of Test Specimen Geometry and Water Soaking on the In Vitro Cytotoxicity of Orthocryl^®, Orthocryl^® LC, Loctite^® EA 9483 and Polypropylene

by Richard Behnke, Franka Stahl, Kathrin Duske, Mareike Warkentin, Margit Schwartz, Burkhard Hinz and Udo Walther

Molecules 2022, 27(12), 3949; https://doi.org/10.3390/molecules27123949 - 20 Jun 2022

Viewed by 1637

Abstract

Depending on their composition, plastics have a cytotoxic potential that needs to be evaluated before they are used in dentistry, e.g., as orthodontic removable appliances. Relevant guidelines set out requirements that a potential new resin in the medical field must meet, with a [...] Read more.

Depending on their composition, plastics have a cytotoxic potential that needs to be evaluated before they are used in dentistry, e.g., as orthodontic removable appliances. Relevant guidelines set out requirements that a potential new resin in the medical field must meet, with a wide scope for experimental design. In the present study, test specimens of different geometries consisting of varying polymers (Orthocryl^®, Orthocryl^® LC, Loctite^® EA 9483, Polypropylene) were soaked for different periods of time, then transferred to cell culture medium for 24 h, which was subsequently used for 24-h cultivation of A549 cells, followed by cytotoxicity assays (WST-1, Annexin V-FITC-propidium iodide (PI) flow cytometry). In this context, a reduction in the cytotoxic effect of the eluates of test specimens prepared from Orthocryl^® LC and Loctite^® EA 9483 was particularly evident in the Annexin V-FITC-PI assay when the soaking time was extended to 48 h and 168 h, respectively. Consistent with this, a reduced release of potentially toxic monomers into the cell culture medium, as measured by gas chromatography-mass spectrometry, was observed when the prior soaking time of test specimens of all geometries was extended. Remarkably, a significant increase in cytotoxic effect was observed in the WST-1 assay, which was accompanied by a higher release of monomers when the thickness of the test sample was increased from 0.5 to 1.0 mm, although an elution volume adapted to the surface area was used. However, further increasing the thickness to 3.0 mm did not lead to an increase in the observed cytotoxicity or monomer release. Test specimens made of polypropylene showed no toxicity under all test specimen sizes and soaking time conditions. Overall, it is recommended to perform toxicity studies of test specimens using different geometries and soaking times. Thereby, the influence of the different specimen thicknesses should also be considered. Finally, an extension of the test protocols proposed in ISO 10993-5:2009 should be considered, e.g., by flow cytometry or monomer analysis as well as fixed soaking times. Full article

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37 pages, 7855 KiB

Open AccessReview

The LAM of the Rings: Large Amplitude Motions in Aromatic Molecules Studied by Microwave Spectroscopy

by Ha Vinh Lam Nguyen, Walther Caminati and Jens-Uwe Grabow

Molecules 2022, 27(12), 3948; https://doi.org/10.3390/molecules27123948 - 20 Jun 2022

Cited by 10 | Viewed by 2946

Abstract

Large amplitude motions (LAMs) form a fundamental phenomenon that demands the development of specific theoretical and Hamiltonian models. In recent years, along with the strong progress in instrumental techniques on high-resolution microwave spectroscopy and computational capacity in quantum chemistry, studies on LAMs have [...] Read more.

Large amplitude motions (LAMs) form a fundamental phenomenon that demands the development of specific theoretical and Hamiltonian models. In recent years, along with the strong progress in instrumental techniques on high-resolution microwave spectroscopy and computational capacity in quantum chemistry, studies on LAMs have become very diverse. Larger and more complex molecular systems have been taken under investigation, ranging from series of heteroaromatic molecules from five- and six-membered rings to polycyclic-aromatic-hydrocarbon derivatives. Such systems are ideally suited to create families of molecules in which the positions and the number of LAMs can be varied, while the heteroatoms often provide a sufficient dipole moment to the systems to warrant the observation of their rotational spectra. This review will summarize three types of LAMs: internal rotation, inversion tunneling, and ring puckering, which are frequently observed in aromatic five-membered rings such as furan, thiophene, pyrrole, thiazole, and oxazole derivatives, in aromatic six-membered rings such as benzene, pyridine, and pyrimidine derivatives, and larger combined rings such as naphthalene, indole, and indan derivatives. For each molecular class, we will present the representatives and summarize the recent insights on the molecular structure and internal dynamics and how they help to advance the field of quantum mechanics. Full article

(This article belongs to the Special Issue Spectroscopic Characterization of Molecular Clusters and Large Amplitude Motions)

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12 pages, 2631 KiB

Open AccessArticle

Changes in Water Properties in Human Tissue after Double Filtration Plasmapheresis—A Case Study

by Felix Scholkmann and Roumiana Tsenkova

Molecules 2022, 27(12), 3947; https://doi.org/10.3390/molecules27123947 - 20 Jun 2022

Cited by 2 | Viewed by 2669

Abstract

Double-filtration plasmapheresis (DFPP) is a blood cleaning technique that enables the removal of unwanted substances from the blood. In our case study, we performed near-infrared (NIR) spectroscopy measurements on the human hand tissue before and after a specific DFPP treatment (INUSpheresis with a [...] Read more.

Double-filtration plasmapheresis (DFPP) is a blood cleaning technique that enables the removal of unwanted substances from the blood. In our case study, we performed near-infrared (NIR) spectroscopy measurements on the human hand tissue before and after a specific DFPP treatment (INUSpheresis with a TKM58 filter), along with NIR measurements of the substances extracted via DFPP (eluate). The spectral data were analyzed using the aquaphotomics approach. The analysis showed that the water properties in the tissue change after DFPP treatment, i.e., an increase in small water clusters, free water molecules and a decrease in hydroxylated water as well as superoxide in hydration shells was noted. The opposite effect was observed in the eluates of both DFPP treatments. Our study is the first that documents changes in water spectral properties after DFPP treatments in human tissue. The changes in tissue water demonstrated by our case study suggest that the positive physiological effects of DFPP in general, and of INUSpheresis with the TKM58 filter in particular, may be associated with improvements in water quality in blood and tissues. Full article

(This article belongs to the Special Issue Aquaphotomics - Exploring Water Molecular Systems in Nature)

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14 pages, 1448 KiB

Open AccessArticle

Benzamides Substituted with Quinoline-Linked 1,2,4-Oxadiazole: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo

by Bin-Long Sun, Ying-Ying Wang, Sen Yang, Min-Ting Tu, Ying-Ying Shao, Yi Hua, Yi Zhou and Cheng-Xia Tan

Molecules 2022, 27(12), 3946; https://doi.org/10.3390/molecules27123946 - 20 Jun 2022

Cited by 4 | Viewed by 1458

Abstract

To develop new compounds with high activity, broad spectrum and low-toxicity, 17 benzamides substituted with quinoline-linked 1,2,4-oxadiazole were designed using the splicing principle of active substructures and were synthesized. The biological activities were evaluated against 10 fungi, indicating that some of the synthetic [...] Read more.

To develop new compounds with high activity, broad spectrum and low-toxicity, 17 benzamides substituted with quinoline-linked 1,2,4-oxadiazole were designed using the splicing principle of active substructures and were synthesized. The biological activities were evaluated against 10 fungi, indicating that some of the synthetic compounds showed excellent fungicidal activities. For example, at 50 mg/L, the inhibitory activity of 13p (3-Cl-4-Cl substituted, 86.1%) against Sclerotinia sclerotiorum was superior to that of quinoxyfen (77.8%), and the inhibitory activity of 13f (3-CF₃ substituted, 77.8%) was comparable to that of quinoxyfen. The fungicidal activities of 13f and 13p to Sclerotinia sclerotiorum were better than that of quinoxyfen (14.19 mg/L), with EC₅₀ of 6.67 mg/L and 5.17 mg/L, respectively. Furthermore, the acute toxicity of 13p was 19.42 mg/L, classifying it as a low-toxic compound. Full article

(This article belongs to the Special Issue Bioactive Molecules: Isolation, Synthesis, Analysis, and Application in Medicinal Chemistry)

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17 pages, 5838 KiB

Open AccessArticle

Design of Novel Enantiopure Dispirooxindolopyrrolidine-Piperidones as Promising Candidates toward COVID-19: Asymmetric Synthesis, Crystal Structure and In Silico Studies

by Amani Toumi, Sarra Boudriga, Yasmine M. Mandour, Ahmed A. Mekki, Michael Knorr, Carsten Strohmann, Jan-Lukas Kirchhoff and Mansour Sobeh

Molecules 2022, 27(12), 3945; https://doi.org/10.3390/molecules27123945 - 20 Jun 2022

Cited by 5 | Viewed by 2202

Abstract

Despite the effectiveness of COVID-19 vaccines, there is still an urgent need for discovering new anti-viral drugs to address the awful spread and transmission of the rapidly modifiable virus. In this study, the ability of a small library of enantiomerically pure spirooxindolopyrrolidine-grafted piperidones [...] Read more.

Despite the effectiveness of COVID-19 vaccines, there is still an urgent need for discovering new anti-viral drugs to address the awful spread and transmission of the rapidly modifiable virus. In this study, the ability of a small library of enantiomerically pure spirooxindolopyrrolidine-grafted piperidones to inhibit the main protease of SARS-CoV-2 (M^pro) is evaluated. These spiroheterocycles were synthesized by 1,3-dipolar cycloaddition of various stabilized azomethine ylides with chiral dipolarophiles derived from N-[(S)-(-)-methylbenzyl]-4-piperidone. The absolute configuration of contiguous carbons was confirmed by a single crystal X-ray diffraction analysis. The binding of these compounds to SARS-CoV-2 M^pro was investigated using molecular docking and molecular dynamics simulation. Three compounds 4a, 4b and 4e exhibited stable binding modes interacting with the key subsites of the substrate-binding pocket of SARS-CoV-2 M^pro. The synthesized compounds represent potential leads for the development of novel inhibitors of SARS-CoV-2 main protease protein for COVID-19 treatment. Full article

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20 pages, 3320 KiB

Open AccessArticle

Properties of Parallel Tetramolecular G-Quadruplex Carrying N-Acetylgalactosamine as Potential Enhancer for Oligonucleotide Delivery to Hepatocytes

by Anna Clua, Santiago Grijalvo, Namrata Erande, Swati Gupta, Kristina Yucius, Raimundo Gargallo, Stefania Mazzini, Muthiah Manoharan and Ramon Eritja

Molecules 2022, 27(12), 3944; https://doi.org/10.3390/molecules27123944 - 20 Jun 2022

Cited by 1 | Viewed by 2447 | Correction

Abstract

The development of oligonucleotide conjugates for in vivo targeting is one of the most exciting areas for oligonucleotide therapeutics. A major breakthrough in this field was the development of multifunctional GalNAc-oligonucleotides with high affinity to asialoglycoprotein receptors (ASGPR) that directed therapeutic oligonucleotides to [...] Read more.

The development of oligonucleotide conjugates for in vivo targeting is one of the most exciting areas for oligonucleotide therapeutics. A major breakthrough in this field was the development of multifunctional GalNAc-oligonucleotides with high affinity to asialoglycoprotein receptors (ASGPR) that directed therapeutic oligonucleotides to hepatocytes. In the present study, we explore the use of G-rich sequences functionalized with one unit of GalNAc at the 3′-end for the formation of tetrameric GalNAc nanostructures upon formation of a parallel G-quadruplex. These compounds are expected to facilitate the synthetic protocols by providing the multifunctionality needed for the binding to ASGPR. To this end, several G-rich oligonucleotides carrying a TGGGGGGT sequence at the 3′-end functionalized with one molecule of N-acetylgalactosamine (GalNAc) were synthesized together with appropriate control sequences. The formation of a self-assembled parallel G-quadruplex was confirmed through various biophysical techniques such as circular dichroism, nuclear magnetic resonance, polyacrylamide electrophoresis and denaturation curves. Binding experiments to ASGPR show that the size and the relative position of the therapeutic cargo are critical for the binding of these nanostructures. The biological properties of the resulting parallel G-quadruplex were evaluated demonstrating the absence of the toxicity in cell lines. The internalization preferences of GalNAc-quadruplexes to hepatic cells were also demonstrated as well as the enhancement of the luciferase inhibition using the luciferase assay in HepG2 cell lines versus HeLa cells. All together, we demonstrate that tetramerization of G-rich oligonucleotide is a novel and simple route to obtain the beneficial effects of multivalent N-acetylgalactosamine functionalization. Full article

(This article belongs to the Special Issue Frontiers in Nucleic Acid Chemistry—in Memory of Professor Enrique Pedroso for His Outstanding Contributions to Nucleic Acid Chemistry)

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19 pages, 7127 KiB

Open AccessArticle

Molybdenum Disulphide Precipitation in Jet Reactors: Introduction of Kinetics Model for Computational Fluid Dynamics Calculations

by Michał Wojtalik, Krzysztof Wojtas, Weronika Gołębiowska, Maria Jarząbek, Wojciech Orciuch and Łukasz Makowski

Molecules 2022, 27(12), 3943; https://doi.org/10.3390/molecules27123943 - 20 Jun 2022

Cited by 1 | Viewed by 1173

Abstract

In our previous work, we used the population balance method to develop a molybdenum disulphide kinetics model consisting of a set of differential equations and constants formulated to express the kinetics of complex chemical reactions leading to molybdenum disulphide precipitation. The purpose of [...] Read more.

In our previous work, we used the population balance method to develop a molybdenum disulphide kinetics model consisting of a set of differential equations and constants formulated to express the kinetics of complex chemical reactions leading to molybdenum disulphide precipitation. The purpose of the study is to improved the model to describe the occurring phenomena more thoroughly and have introduced computational fluid dynamics (CFD) modelling to conduct calculations for various reactor geometries. CFD simulations supplemented with our nucleation and growth kinetics model can predict the impact of mixing conditions on particle size with good accuracy. This introduces another engineering tool for designing efficient chemical reactors. Full article

(This article belongs to the Section Applied Chemistry)

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9 pages, 3251 KiB

Open AccessArticle

Graphene Oxide-Sensitized Surface Plasmon Resonance Biosensor of Porcine Reproductive and Respiratory Syndrome Virus

by Xuemei Liu, Chao Xu, Chunyu Fu, Dongfang Xia, Fuchao Wang, Hongzong Yin and Jun Peng

Molecules 2022, 27(12), 3942; https://doi.org/10.3390/molecules27123942 - 20 Jun 2022

Cited by 3 | Viewed by 1313

Abstract

Biosensor analysis based on the surface plasmon resonance (SPR) phenomenon enables label-free, highly sensitive analyte detection without prior sample purification or processing. However, potential applications of SPR biosensors in virus detection in biological samples remain to be explored. Owing to its excellent biocompatibility [...] Read more.

Biosensor analysis based on the surface plasmon resonance (SPR) phenomenon enables label-free, highly sensitive analyte detection without prior sample purification or processing. However, potential applications of SPR biosensors in virus detection in biological samples remain to be explored. Owing to its excellent biocompatibility and abundance of hydroxyl and carboxyl functional groups, graphene oxide (GO) has been widely used as a biosensor of proteins and metal ions in living cells. The present work explored the effect of GO modification on the sensitivity of an SPR biosensor and used a GO-modified sensor to detect porcine reproductive and respiratory syndrome virus in cell culture, as shown. The GO modification markedly enhanced the sensitivity of the Fourier transform SPR sensor and enabled linear detection of porcine reproductive and respiratory syndrome virus (PRRSV) with a multiplicity of infection in the range 0.2–1.7 (R² = 0.998). Such a GO-modified sensor provides a promising alternative for virus detection. Full article

(This article belongs to the Special Issue Molecular Toxicology and Cancer Prevention)

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26 pages, 1640 KiB

Open AccessReview

Theragnostic Applications of Mammal and Plant-Derived Extracellular Vesicles: Latest Findings, Current Technologies, and Prospects

by Nada Basheir Ali, Ahmad Faizal Abdull Razis, Der Jiun Ooi, Kim Wei Chan, Norsharina Ismail and Jhi Biau Foo

Molecules 2022, 27(12), 3941; https://doi.org/10.3390/molecules27123941 - 20 Jun 2022

Cited by 9 | Viewed by 3126

Abstract

The way cells communicate is not fully understood. However, it is well-known that extracellular vesicles (EVs) are involved. Researchers initially thought that EVs were used by cells to remove cellular waste. It is now clear that EVs function as signaling molecules released by [...] Read more.

The way cells communicate is not fully understood. However, it is well-known that extracellular vesicles (EVs) are involved. Researchers initially thought that EVs were used by cells to remove cellular waste. It is now clear that EVs function as signaling molecules released by cells to communicate with one another, carrying a cargo representing the mother cell. Furthermore, these EVs can be found in all biological fluids, making them the perfect non-invasive diagnostic tool, as their cargo causes functional changes in the cells upon receiving, unlike synthetic drug carriers. EVs last longer in circulation and instigate minor immune responses, making them the perfect drug carrier. This review sheds light on the latest development in EVs isolation, characterization and, application as therapeutic cargo, novel drug loading techniques, and diagnostic tools. We also address the advancement in plant-derived EVs, their characteristics, and applications; since plant-derived EVs only recently gained focus, we listed the latest findings. Although there is much more to learn about, EV is a wide field of research; what scientists have discovered so far is fascinating. This paper is suitable for those new to the field seeking to understand EVs and those already familiar with it but wanting to review the latest findings. Full article

(This article belongs to the Section Applied Chemistry)

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19 pages, 4947 KiB

Open AccessArticle

Preparation, Characterization, and In Vitro Release of Curcumin-Loaded IRMOF-10 Nanoparticles and Investigation of Their Pro-Apoptotic Effects on Human Hepatoma HepG2 Cells

by Dongge Yin, Xueling Hu, Mengru Cai, Kaixin Wang, Hulinyue Peng, Jie Bai, Yvchen Xv, Tingting Fu, Xiaoxv Dong, Jian Ni and Xingbin Yin

Molecules 2022, 27(12), 3940; https://doi.org/10.3390/molecules27123940 - 20 Jun 2022

Cited by 6 | Viewed by 2067

Abstract

Curcumin (CUR) has a bright future in the treatment of cancer as a natural active ingredient with great potential. However, curcumin has a low solubility, which limits its clinical application. In this study, IRMOF-10 was created by the direct addition of triethylamine, CUR [...] Read more.

Curcumin (CUR) has a bright future in the treatment of cancer as a natural active ingredient with great potential. However, curcumin has a low solubility, which limits its clinical application. In this study, IRMOF-10 was created by the direct addition of triethylamine, CUR was loaded into IRMOF-10 using the solvent adsorption method, and the two were characterized using a scanning electron microscope (SEM), X-ray diffraction (XRD), dynamic light scattering (DLS), Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TG) methods, and Brunauer–Emmett–Teller (BET) analysis. We also used the MTT method, 4′,6-diamidino-2-phenylindole (DAPI) staining, the annexin V/PI method, cellular uptake, reactive oxygen species (ROS), and the mitochondrial membrane potential (MMP) to perform a safety analysis and anticancer activity study of IRMOF-10 and CUR@IRMOF-10 on HepG2 cells. Our results showed that CUR@IRMOF-10 had a CUR load of 63.96%, with an obvious slow-release phenomenon. The CUR levels released under different conditions at 60 h were 33.58% (pH 7.4) and 31.86% (pH 5.5). Cell experiments proved that IRMOF-10 was biologically safe and could promote curcumin entering the nucleus, causing a series of reactions, such as an increase in reactive oxygen species and a decrease in the mitochondrial membrane potential, thereby leading to cell apoptosis. In summary, IRMOF-10 is an excellent drug carrier and CUR@IRMOF-10 is an effective anti-liver cancer sustained-release preparation. Full article

(This article belongs to the Special Issue Potential Applications of Functional Porous Organic Frameworks)

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12 pages, 3001 KiB

Open AccessArticle

Facile Synthesis of Porous Ag Crystals as SERS Sensor for Detection of Five Methamphetamine Analogs

by Yazhou Qin, Fan Mo, Sen Yao, Yuanzhao Wu, Yingsheng He and Weixuan Yao

Molecules 2022, 27(12), 3939; https://doi.org/10.3390/molecules27123939 - 20 Jun 2022

Cited by 7 | Viewed by 1711

Abstract

Porous noble metal nanomaterials have attracted extensive attention due to their high specific surface area and surface plasmon resonance effect. However, it is difficult to form porous structures due to the high mobility and low reduction potential of noble metal precursors. In this [...] Read more.

Porous noble metal nanomaterials have attracted extensive attention due to their high specific surface area and surface plasmon resonance effect. However, it is difficult to form porous structures due to the high mobility and low reduction potential of noble metal precursors. In this article, we developed a facile method for preparing porous Ag with a controllable structure at room temperature. Two kinds of Ag crystals with different porous structures were successfully prepared by using AgCl cubes as sacrificial templates. Through the galvanic replacement reaction of Zn and AgCl, Ag crystals with a sponge-like porous structure were successfully prepared. Additionally, using NaBH₄ as the reducing agent, we prepared granular porous Ag cubes by optimizing the amount of reducing agent. Both the sponge-like and granular porous Ag cubes have clean and accessible surfaces. In addition, we used the prepared two porous Ag cubes as substrate materials for SERS detection of five kinds of methamphetamine analogs. The experimental results show that the enhancement effect of granular porous Ag is better than that of sponge-like porous Ag. Furthermore, we probed the hot spot distribution of granular porous Ag by Raman mapping. By using granular porous Ag as the substrate material, we have achieved trace detection of 5 kinds of methamphetamine analogs including Ephedrine, Amphetamine, N-Methyl-1-(benzofuran-5-yl)propan-2-amine (5-MAPB), N-Methyl-1-(4-methoxyphenyl)propan-2-amine (PMMA) and N-Methyl-1-(4-fluorophenyl)propan-2-amine (4-FMA). Furthermore, to achieve qualitative differentiation of analogs with similar structures we performed density functional theoretical (DFT) calculations on the Raman spectra of the above analogs. The DFT calculations provided the vibrational frequencies, Raman activities, and normal mode assignment for each analog, enabling the qualitative differentiation of the above analogs. Full article

(This article belongs to the Special Issue Advances in Resonant Nanostructures and Their Applications in Molecular Spectroscopy and Sensing)

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20 pages, 5199 KiB

Open AccessArticle

Simultaneous Removal of Heavy Metals (Cu, Cd, Cr, Ni, Zn and Pb) from Aqueous Solutions Using Thermally Treated Romanian Zeolitic Volcanic Tuff

by Marin Senila, Emilia Neag, Oana Cadar, Emoke Dalma Kovacs, Ioan Aschilean and Melinda Haydee Kovacs

Molecules 2022, 27(12), 3938; https://doi.org/10.3390/molecules27123938 - 20 Jun 2022

Cited by 16 | Viewed by 2563

Abstract

Increased concentrations of heavy metals in the environment are of public health concern, their removal from waters receiving considerable interest. The aim of this paper was to study the simultaneous adsorption of heavy metals (Cu, Cd, Cr, Ni, Zn and Pb) from aqueous [...] Read more.

Increased concentrations of heavy metals in the environment are of public health concern, their removal from waters receiving considerable interest. The aim of this paper was to study the simultaneous adsorption of heavy metals (Cu, Cd, Cr, Ni, Zn and Pb) from aqueous solutions using the zeolitic volcanic tuffs as adsorbents. The effect of thermal treatment temperature, particle size and initial metal concentrations on the metal ions sorption was investigated. The selectivity of used zeolite for the adsorption of studied heavy metals followed the order: Pb > Cr > Cu > Zn > Cd > Ni. The removal efficiency of the heavy metals was strongly influenced by the particle sizes, the samples with smaller particle size (0–0.05 mm) being more efficient in heavy metals removal than those with larger particle size (1–3 mm). Generally, no relevant changes were observed in heavy metals removal efficiency for the treatment temperatures of 200 °C and 350 °C. Moreover, at a higher temperature (550 °C), a decrease in the removal efficiencies was observed. The Cd, Zn, Cu, Cr, Zn and Ni sorption was best described by Langmuir model according to the high values of correlation coefficient. The pseudo-first-order kinetic model presented the best correlation of the experimental data. Full article

(This article belongs to the Special Issue Advanced Analytical Techniques in Environmental Chemistry)

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19 pages, 453 KiB

Open AccessReview

Biological Activities of Organic Extracts of the Genus Aristolochia: A Review from 2005 to 2021

by Martín A. Lerma-Herrera, Lidia Beiza-Granados, Alejandra Ochoa-Zarzosa, Joel E. López-Meza, Pedro Navarro-Santos, Rafael Herrera-Bucio, Judit Aviña-Verduzco and Hugo A. García-Gutiérrez

Molecules 2022, 27(12), 3937; https://doi.org/10.3390/molecules27123937 - 20 Jun 2022

Cited by 9 | Viewed by 2916

Abstract

Different ethnomedicinal studies have investigated the relationship between various phytochemicals as well as organic extracts and their bioactive aspects. Studies on biological effects are attributed to secondary metabolites such as alkaloids, phenolic compounds, and terpenes. Since there have been no reviews in the [...] Read more.

Different ethnomedicinal studies have investigated the relationship between various phytochemicals as well as organic extracts and their bioactive aspects. Studies on biological effects are attributed to secondary metabolites such as alkaloids, phenolic compounds, and terpenes. Since there have been no reviews in the literature on the traditional, phytochemical, and ethnomedicinal uses of the genus Aristolochia so far, this article systematically reviews 141 published studies that analyze the associations between secondary metabolites present in organic extracts and their beneficial effects. Most studies found associations between individual secondary metabolites and beneficial effects such as anticancer activity, antibacterial, antioxidant activity, snake anti-venom and anti-inflammatory activity. The aim of this review was to analyze studies carried out in the period 2005–2021 to update the existing knowledge on different species of the genus Aristolochia for ethnomedicinal uses, as well as pharmacological aspects and therapeutic uses. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

7 pages, 2034 KiB

Open AccessArticle

The Glu143 Residue Might Play a Significant Role in T20 Peptide Binding to HIV-1 Receptor gp41: An In Silico Study

by Ahmed L. Alaofi

Molecules 2022, 27(12), 3936; https://doi.org/10.3390/molecules27123936 - 20 Jun 2022

Cited by 3 | Viewed by 1282

Abstract

Despite the enormous efforts made to develop other fusion inhibitors for HIV, the enfuvirtide (known as T20) peptide is the only approved HIV-1 inhibitory drug so far. Investigating the role of potential residues of the T20 peptide’s conformational dynamics could help us to [...] Read more.

Despite the enormous efforts made to develop other fusion inhibitors for HIV, the enfuvirtide (known as T20) peptide is the only approved HIV-1 inhibitory drug so far. Investigating the role of potential residues of the T20 peptide’s conformational dynamics could help us to understand the role of potential residues of the T20 peptide. We investigated T20 peptide conformation and binding interactions with the HIV-1 receptor (i.e., gp41) using MD simulations and docking techniques, respectively. Although the mutation of E143 into alanine decreased the flexibility of the E143A mutant, the conformational compactness of the mutant was increased. This suggests a potential role of E143 in the T20 peptide’s conformation. Interestingly, the free energy landscape showed a significant change in the wild-type T20 minimum, as the E143A mutant produced two observed minima. Finally, the docking results of T20 to the gp41 receptor showed a different binding interaction in comparison to the E143A mutant. This suggests that E143 residue can influence the binding interaction with the gp41 receptor. Overall, the E143 residue showed a significant role in conformation and binding to the HIV-1 receptor. These findings can be helpful in optimizing and developing HIV-1 inhibitor peptides. Full article

(This article belongs to the Special Issue Molecular Modeling: Advancements and Applications)

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16 pages, 1260 KiB

Open AccessArticle

A Metabolomic Analysis of Cirrhotic Ascites

by Diren Beyoğlu, Cedric Simillion, Federico Storni, Andrea De Gottardi and Jeffrey R. Idle

Molecules 2022, 27(12), 3935; https://doi.org/10.3390/molecules27123935 - 20 Jun 2022

Cited by 4 | Viewed by 2278

Abstract

Ascites is a common complication of decompensated liver cirrhosis, and yet relatively little is known about its biochemical composition. We conducted two metabolomic investigations, comparing the profile of ascites from 33 cirrhotic patients and postoperative peritoneal drainage fluid from 33 surgical patients ( [...] Read more.

Ascites is a common complication of decompensated liver cirrhosis, and yet relatively little is known about its biochemical composition. We conducted two metabolomic investigations, comparing the profile of ascites from 33 cirrhotic patients and postoperative peritoneal drainage fluid from 33 surgical patients (Experiment 1). The profile of paired ascites and plasma was also compared in 17 cirrhotic patients (Experiment 2). Gas chromatography–mass spectrometry-based metabolomics identified 29 metabolites that significantly characterized ascites fluid, whether postoperative drainage fluid or plasma were used as controls. Ten elevated amino acids (glutamine, proline, histidine, tyrosine, glycine, valine, threonine, methionine, lysine, phenylalanine) and seven diminished lipids (laurate, myristate, palmitate, oleate, vaccenate, stearate, cholesterol) largely comprised the cirrhotic ascites metabolomic phenotype that differed significantly (adjusted p < 0.002 to 0.03) from peritoneal drainage fluid or plasma. The pattern of upregulated amino acids in cirrhotic ascites did not indicate albumin proteolysis by peritoneal bacteria. Bidirectional clustering showed that the more severe the cirrhosis, the lower the lipid concentration in ascitic fluid. The metabolomic compartment of ascites in patients with decompensated cirrhosis is characterized by increased amino acids and decreased lipids. These novel findings have potential relevance for diagnostic purposes. Full article

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20 pages, 11451 KiB

Open AccessArticle

Synthesis and Antileukemia Activity Evaluation of Benzophenanthridine Alkaloid Derivatives

by Yaling Tang, Xinglian Xu, Jiang Li, Lulu Deng and Shuzhen Mu

Molecules 2022, 27(12), 3934; https://doi.org/10.3390/molecules27123934 - 19 Jun 2022

Cited by 2 | Viewed by 1696

Abstract

Thirty-three benzophenanthridine alkaloid derivatives (1a–1u and 2a–2l) were synthesized, and their cytotoxic activities against two leukemia cell lines (Jurkat Clone E6-1 and THP-1) were evaluated in vitro using a Cell Counting Kit-8 (CCK-8) assay. Nine of these [...] Read more.

Thirty-three benzophenanthridine alkaloid derivatives (1a–1u and 2a–2l) were synthesized, and their cytotoxic activities against two leukemia cell lines (Jurkat Clone E6-1 and THP-1) were evaluated in vitro using a Cell Counting Kit-8 (CCK-8) assay. Nine of these derivatives (1i–l, 2a, and 2i–l) with IC₅₀ values in the range of 0.18–7.94 μM showed significant inhibitory effects on the proliferation of both cancer cell lines. Analysis of the primary structure–activity relationships revealed that different substituent groups at the C-6 position might have an effect on the antileukemia activity of the corresponding compounds. In addition, the groups at the C-7 and C-8 positions could influence the antileukemia activity. Among these compounds, 2j showed the strongest in vitro antiproliferative activity against Jurkat Clone E6-1 and THP-1 cells with good IC₅₀ values (0.52 ± 0.03 μM and 0.48 ± 0.03 μM, respectively), slightly induced apoptosis, and arrested the cell-cycle, all of which suggests that compound 2j may represent a potentially useful start point to undergo further optimization toward a lead compound. Full article

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