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Advances in Ultrasound Chemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Ultrasound Chemistry".

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 22986

Special Issue Editors


E-Mail Website1 Website2
Guest Editor
Chemistry Department, Alexandru Ioan Cuza University of Iasi, 700506 Iasi, Romania
Interests: diazines; medicinal chemistry; anticancer; antituberculosis; microwave; ultrasounds; organic synthesis
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Chemistry Department, Alexandru Ioan Cuza University of Iasi, 700506 Iasi, Romania
Interests: diazoles; medicinal chemistry; anticancer; antituberculosis; ultrasounds; microwave; organic synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Within the last few decades, ultrasound (US)-assisted reactions have become a widely used and powerful method in organic chemistry synthesis, offering some important advantages, such as significantly faster reaction times, milder conditions, increased yield and selectivity, lower costs, and simplicity in handling and processing. Moreover, in recent years, this method combined with other unconventional methods (microwave (MW)) seems to bring new advantages in terms of the synthetic approach. Taking into consideration the advantages offered by US irradiation in terms of energy consumption diminution, these reactions could be considered environmentally friendly.

The aim of this Special Issue is to provide a platform to present the latest developments in US-assisted reactions in organic chemistry, focused on the synthesis of (but not only) biologically active heterocycle derivatives.

Dr. Gheorghita Zbancioc
Prof. Dr. Costel Moldoveanu
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • ultrasound
  • ultrasound and microwaves
  • organic synthesis
  • heterocycles
  • cycloadditions
  • anticancer
  • antituberculosis
  • antimicrobials
  • anti-HIV
  • other biological activities
  • fluorescent derivatives

Related Special Issue

Published Papers (10 papers)

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Research

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12 pages, 3604 KiB  
Article
Ultrasonic Transformation of Antibiotic Molecules into a Selective Chemotherapeutic Nanodrug
by Haiyan Zhu, Sukhvir Kaur Bhangu, Muthupandian Ashokkumar and Francesca Cavalieri
Molecules 2023, 28(13), 4927; https://doi.org/10.3390/molecules28134927 - 22 Jun 2023
Viewed by 945
Abstract
Ultrasound-based engineering of carrier-free nanodrugs by supramolecular self-assembly has recently emerged as an innovative and environmentally friendly synthetic approach. By applying high-frequency sound waves (490 kHz) in aqueous solutions, the transformation of small chemotherapeutic and antibiotic drug molecules into carrier-free nanodrugs with anticancer [...] Read more.
Ultrasound-based engineering of carrier-free nanodrugs by supramolecular self-assembly has recently emerged as an innovative and environmentally friendly synthetic approach. By applying high-frequency sound waves (490 kHz) in aqueous solutions, the transformation of small chemotherapeutic and antibiotic drug molecules into carrier-free nanodrugs with anticancer and antimicrobial activities was recently achieved. The transformation of the antibiotic drug molecules, i.e., doxycycline, into stable nanodrugs (~130 nm) with selective anticancer activity was achieved without requiring organic solvents, chemical agents, or surfactants. The obtained nanodrug exhibited reactive oxygen species (ROS)-mediated cytotoxicity on human breast cancer (MDA-MB 231 cells) but a negligible antiproliferative effect on healthy fibroblast cells. Imaging by super-resolution microscopy (STORM) provided insights into the intracellular trafficking and endosomal escape of the nanodrugs. Overall, these findings suggest that small antibiotic drugs can be transformed into chemotherapeutic nanodrugs with high selectivity against cancer cells. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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21 pages, 4403 KiB  
Article
Green and Sustainable Ultrasound-Assisted Anodic Electrochemical Preparation of Graphene Oxide Dispersions and Their Antioxidant Properties
by Daria-Maria V. Ratova, Ivan V. Mikheev, Grigoryi R. Chermashentsev, Konstantin I. Maslakov, Sergei Yu. Kottsov, Dmitrii N. Stolbov, Sergey V. Maksimov, Madina M. Sozarukova, Elena V. Proskurnina and Mikhail A. Proskurnin
Molecules 2023, 28(7), 3238; https://doi.org/10.3390/molecules28073238 - 05 Apr 2023
Cited by 2 | Viewed by 1615
Abstract
A fast method for preparing aqueous graphene oxide (GO) dispersions by electrochemical oxidation of a graphite anode without preliminary intercalation with oxidizing agents is proposed. Ultrasonic probing was used in the modulation mode of ultrasonic waves (work/rest) for more efficient graphite oxidation–exfoliation. It [...] Read more.
A fast method for preparing aqueous graphene oxide (GO) dispersions by electrochemical oxidation of a graphite anode without preliminary intercalation with oxidizing agents is proposed. Ultrasonic probing was used in the modulation mode of ultrasonic waves (work/rest) for more efficient graphite oxidation–exfoliation. It is shown that the 4/2 s mode of ultrasonic modulation is the most effective due to the probe material’s low corrosion while maintaining the optimum synthesis temperature not exceeding 30–35 °C and achieving the best characteristics of the resulting product. Three cases of anodic oxidation of graphite to obtain graphene oxide were considered: (1) a combined cathode–anode compartment, (2) a split cathode–anode salt-bridged compartment, and (3) separated anode compartment with a 3.5 kDa dialysis membrane. It was determined that the approach to synthesis with a divided cathode–anode compartment makes it possible to obtain GO sheets with fewer defects compared to chemical methods or methods with a combined cathode–anode compartment and makes it possible to control the oxidation degree of the material (C:O ratio) by varying the current density. The prepared samples showed good stability for more than six months. The spectral and morphological characteristics were studied. Using chemiluminometry in the luminol/Co(II)/H2O2 system, the antioxidant properties concerning three key reactive oxygen species (H2O2, superoxide anion radical, and hydroxyl radical) were demonstrated. It was also shown that the prepared GO dispersions do not induce lipid and phospholipid peroxidation. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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12 pages, 1788 KiB  
Article
Utilizing Contrast-Enhanced Ultrasonography with Phosphatidylserine Microbubbles to Detect Placental Inflammation in Rhesus Macaques
by Rachel C. Wilson, Jamie O. Lo, Gabriel Romero Jimenez, Jonathan R. Lindner, Ov D. Slayden and Victoria H. J. Roberts
Molecules 2023, 28(7), 2894; https://doi.org/10.3390/molecules28072894 - 23 Mar 2023
Cited by 1 | Viewed by 1273
Abstract
The ability to comprehensively monitor physiological and detect pathophysiologic processes early during pregnancy can reduce maternal and fetal morbidity and mortality. Contrast-enhanced ultrasound (CEUS) is a non-invasive imaging technology that utilizes the acoustic detection of microbubbles to examine vascular spaces. Furthermore, microbubbles conjugated [...] Read more.
The ability to comprehensively monitor physiological and detect pathophysiologic processes early during pregnancy can reduce maternal and fetal morbidity and mortality. Contrast-enhanced ultrasound (CEUS) is a non-invasive imaging technology that utilizes the acoustic detection of microbubbles to examine vascular spaces. Furthermore, microbubbles conjugated to specific compounds can focus studies on precise physiological pathways. We hypothesized that CEUS with phosphatidylserine microbubbles (MB-PS) could be employed to monitor placental inflammation. We tested this hypothesis in rhesus macaques (Macaca mulatta), a translational and relevant animal model of human placental health. As placental inflammation impacts many at-risk pregnancies, we performed CEUS with MB-PS in pregnant macaques fed a high-fat diet (e.g., a western-style diet, WSD) in the presence or absence of testosterone (T) to mimic the increased risk of polycystic ovary syndrome and subfertility. We have previously demonstrated a placental inflammation phenotype in this model, and, thus, we related the MB-PS CEUS signal intensity to placental inflammation markers: selectin p and angiopoietins. Testosterone exposure increased the MB-PS signal in the placental microcirculation on the maternal side compared to control animals. We found that T increased placental weight and decreased angiopoietin 2 (ANGPT2) immunoreactivity. Furthermore, a significant inverse correlation was found between MB-PS signal and ANGPT2. This indicated that CEUS with MB-PS can be used to monitor placental parameters. We propose that CEUS with MB-PS could aid in the identification of pregnancies at risk of placental vascular compromise. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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21 pages, 7677 KiB  
Article
Ultrasound-Assisted Extraction of Blackberry Seed Oil: Optimization and Oil Characterization
by Petronela L. Matei, Iuliana Deleanu, Ana M. Brezoiu, Nicoleta A. Chira, Cristina Busuioc, Gabriela Isopencu, Mihaela Cîlțea-Udrescu, Elvira Alexandrescu and Anicuta Stoica-Guzun
Molecules 2023, 28(6), 2486; https://doi.org/10.3390/molecules28062486 - 08 Mar 2023
Cited by 4 | Viewed by 1966
Abstract
Ultrasound-assisted extraction (UAE) was applied to extract oil from blackberry (BB) seeds. The effect of UAE conditions on oil recovery and quality was investigated. Favorable experimental conditions (ultrasound intensity (UI), extraction temperature, and time) were investigated using response surface methodology (RSM). A Box–Behnken [...] Read more.
Ultrasound-assisted extraction (UAE) was applied to extract oil from blackberry (BB) seeds. The effect of UAE conditions on oil recovery and quality was investigated. Favorable experimental conditions (ultrasound intensity (UI), extraction temperature, and time) were investigated using response surface methodology (RSM). A Box–Behnken design was used to predict optimized conditions for BB seed oil extraction. These conditions were as follows: 13.77 W/cm2 UI, 45 °C extraction temperature, and 15 min extraction time. The experimental value obtained for extraction efficiency under optimal conditions was 87 ± 0.34%, in good agreement with the optimized predicted value. UAE does not affect the oil composition and confers higher antioxidant values in BB seed oil in comparison with Soxhlet extraction. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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21 pages, 2325 KiB  
Article
Improving the Functional Performance of Date Seed Protein Concentrate by High-Intensity Ultrasonic Treatment
by Mohamed Kelany and Oktay Yemiş
Molecules 2023, 28(1), 209; https://doi.org/10.3390/molecules28010209 - 26 Dec 2022
Cited by 4 | Viewed by 1618
Abstract
Date kernel is a plant-derived byproduct that has the potential to be converted into a high-value-added food ingredient, such as protein concentrate, in the food industry. Ultrasound, which is an alternative method for improving the functional properties of food proteins, is an effective [...] Read more.
Date kernel is a plant-derived byproduct that has the potential to be converted into a high-value-added food ingredient, such as protein concentrate, in the food industry. Ultrasound, which is an alternative method for improving the functional properties of food proteins, is an effective physical treatment for modifying protein functionality. Solubility is the main criterion that primarily affects other functional properties of protein concentrates, such as emulsification, foaming, and water and oil binding. The aim of this study is to enhance the techno-functional performance of date seed protein concentrate (DSPC) by maximizing the solubility via a high-intensity ultrasound (HIUS) treatment at a fixed frequency of 20 kHz. The effect of ultrasonic homogenization under varying amplitudes and times (amplitude of 40, 60, and 80% for 5, 10, and 15 min, respectively) on the functional properties of the DSPC was investigated by using the response surface methodology (RSM). A face-centered central composite design (FC-CCD) revealed that the optimal process conditions of HIUS were at an amplitude of 80% for 15 min. The physicochemical and functional properties of the ultrasound-applied concentrate (DSPC-US) were determined under the optimum HIUS conditions, and then these properties of DSPC-US were compared to the native DSPC. The results showed that the solubility of all DSPC samples treated by HIUS was significantly (p < 0.05) higher than that of the native DSPC. In addition, emulsion activity/stability, foaming activity/stability, and oil-binding capacity increased after HIUS homogenization treatments, whereas the water-binding capacity decreased. These changes in the techno-functional properties of the DSPC-US were explained by the modification to the physicochemical structure of the DSPC (particle size, zeta potential, SDS-PAGE, SEM, FTIR, DSC, free SH content, surface hydrophobicity, and intrinsic emission). This work revealed that HIUS could be an effective treatment for enhancing the functional properties of date seed protein concentrate. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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20 pages, 3715 KiB  
Article
Surfactant-Mediated Ultrasonic-Assisted Extraction and Purification of Antioxidants from Chaenomeles speciosa (Sweet) Nakai for Chemical- and Cell-Based Antioxidant Capacity Evaluation
by Fuxia Hu, Feng Li, Zhenjia Zheng, Dongxiao Sun-Waterhouse and Zhaosheng Wang
Molecules 2022, 27(22), 7970; https://doi.org/10.3390/molecules27227970 - 17 Nov 2022
Cited by 3 | Viewed by 1211
Abstract
In this study, a surfactant-mediated ultrasonic-assisted process was used for the first time to produce an antioxidant-enriched extract from Chaenomeles speciosa (Sweet) Nakai (C. speciosa, a popular fruit grown widely in the temperate regions of China). Ultrasonic treatment at 51 °C [...] Read more.
In this study, a surfactant-mediated ultrasonic-assisted process was used for the first time to produce an antioxidant-enriched extract from Chaenomeles speciosa (Sweet) Nakai (C. speciosa, a popular fruit grown widely in the temperate regions of China). Ultrasonic treatment at 51 °C and 200 W for 30 min with sodium dodecyl sulfate as the surfactant led to a phenolic yield of 32.42 mg/g from dried C. speciosa powder, based on single-factor experiments, the Plackett–Burman design and the Box–Behnken design. The phenolic content increased from 6.5% (the crude extract) to 57% (the purified extract) after the purification, using LSA-900C macroporous resin. Both the crude and purified extracts exhibited a significant total reducing power and DPPH/ABTS scavenging abilities, with the purified extract being more potent. The purified extract exerted significant antioxidant actions in the tert-butyl hydroperoxide-stimulated HepG2 cells, e.g., increasing the activities of superoxide dismutase and catalase, while decreasing the reactive oxygen species and malondialdehyde levels, through the regulation of the genes and proteins of the Nrf2/Keap1 signaling pathway. Therefore, the extract from C. speciosa is a desirable antioxidant agent for the oxidative damage of the body to meet the rising demand for natural therapeutics. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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13 pages, 15664 KiB  
Article
Fluorescent Azasteroids through Ultrasound Assisted Cycloaddition Reactions
by Costel Moldoveanu, Ionel Mangalagiu and Gheorghita Zbancioc
Molecules 2021, 26(16), 5098; https://doi.org/10.3390/molecules26165098 - 23 Aug 2021
Cited by 6 | Viewed by 1705
Abstract
We report here the synthesis and optical spectral properties of several new azasteroid derivatives. The formation of these compounds was explained based on the most probable mechanism. The luminescent heterocycles were synthesized by 1,3-dipolar cycloaddition reactions between benzo[f]quinoline and methylpropiolate or dimethyl acetylenedicarboxylate [...] Read more.
We report here the synthesis and optical spectral properties of several new azasteroid derivatives. The formation of these compounds was explained based on the most probable mechanism. The luminescent heterocycles were synthesized by 1,3-dipolar cycloaddition reactions between benzo[f]quinoline and methylpropiolate or dimethyl acetylenedicarboxylate (DMAD). A selective and efficient way for [3+2]-dipolar cycloaddition of benzo[f]quinolinium ylides under ultrasound (US) irradiation (20 kHz processing frequency) is presented. We report substantially higher yields under US irradiation, whereas the solvent amounts required are at least three-fold less compared to classical heating. The azasteroid derivatives are blue emitters with λmax of fluorescence around 430–450 nm. A certain influence of the azasteroid substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky pivaloyl group or without a C=O carbonyl group have shown increased fluorescence intensity. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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Review

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29 pages, 4566 KiB  
Review
Recent Developments in Sonochemical Synthesis of Nanoporous Materials
by Sylwia Głowniak, Barbara Szczęśniak, Jerzy Choma and Mietek Jaroniec
Molecules 2023, 28(6), 2639; https://doi.org/10.3390/molecules28062639 - 14 Mar 2023
Cited by 17 | Viewed by 4750
Abstract
Ultrasounds are commonly used in medical imaging, solution homogenization, navigation, and ranging, but they are also a great energy source for chemical reactions. Sonochemistry uses ultrasounds and thus realizes one of the basic concepts of green chemistry, i.e., energy savings. Moreover, reduced reaction [...] Read more.
Ultrasounds are commonly used in medical imaging, solution homogenization, navigation, and ranging, but they are also a great energy source for chemical reactions. Sonochemistry uses ultrasounds and thus realizes one of the basic concepts of green chemistry, i.e., energy savings. Moreover, reduced reaction time, mostly using water as a solvent, and better product yields are among the many factors that make ultrasound-induced reactions greener than those performed under conventional conditions. Sonochemistry has been successfully implemented for the preparation of various materials; this review covers sonochemically synthesized nanoporous materials. For instance, sonochemical-assisted methods afforded ordered mesoporous silicas, spherical mesoporous silicas, periodic mesoporous organosilicas, various metal oxides, biomass-derived activated carbons, carbon nanotubes, diverse metal-organic frameworks, and covalent organic frameworks. Among these materials, highly porous samples have also been prepared, such as garlic peel-derived activated carbon with an apparent specific surface area of 3887 m2/g and MOF-177 with an SSA of 4898 m2/g. Additionally, many of them have been examined for practical usage in gas adsorption, water treatment, catalysis, and energy storage-related applications, yielding satisfactory results. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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20 pages, 7680 KiB  
Review
Wittig and Wittig–Horner Reactions under Sonication Conditions
by Gheorghe Ilia, Vasile Simulescu, Nicoleta Plesu, Vlad Chiriac and Petru Merghes
Molecules 2023, 28(4), 1958; https://doi.org/10.3390/molecules28041958 - 18 Feb 2023
Cited by 1 | Viewed by 3825
Abstract
Carbonyl olefinations are among the most important organic syntheses that form C=C bonds, as they usually have high yields and in addition offer excellent stereoselectivity. Due to these advantages, carbonyl olefinations have important pharmaceutical and industrial applications. These reactions contain an additional step [...] Read more.
Carbonyl olefinations are among the most important organic syntheses that form C=C bonds, as they usually have high yields and in addition offer excellent stereoselectivity. Due to these advantages, carbonyl olefinations have important pharmaceutical and industrial applications. These reactions contain an additional step of an α-functionalized carbanion to an aldehyde or ketone to produce alkenes, but syntheses performed using metal carbene complexes are also known. The Wittig reaction is an example of carbonyl olefination, one of the best ways to synthesize alkenes. This involves the chemical reaction between an aldehyde or ketone with a so-called Wittig reagent, for instance phosphonium ylide. Triphenylphosphine-derived ylides and trialkylphosphine-derived ylides are the most common phosphorous compounds used as Wittig reagents. The Wittig reaction is commonly involved in the synthesis of novel anti-cancer and anti-viral compounds. In recent decades, the use of ultrasound on the Wittig reaction (and on different modified Wittig syntheses, such as the Wittig–Horner reaction or the aza-Wittig method) has been studied as a green synthesis. In addition to the advantage of green synthesis, the use of ultrasounds in general also improved the yield and reduced the reaction time. All of these chemical syntheses conducted under ultrasound will be described further in the present review. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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20 pages, 1333 KiB  
Review
Low-Frequency Ultrasound Coupled with High-Pressure Technologies: Impact of Hybridized Techniques on the Recovery of Phytochemical Compounds
by Giovani Leone Zabot, Juliane Viganó and Eric Keven Silva
Molecules 2021, 26(17), 5117; https://doi.org/10.3390/molecules26175117 - 24 Aug 2021
Cited by 15 | Viewed by 2655
Abstract
The coupling of innovative technologies has emerged as a smart alternative for the process intensification of bioactive compound extraction from plant matrices. In this regard, the development of hybridized techniques based on the low-frequency and high-power ultrasound and high-pressure technologies, such as supercritical [...] Read more.
The coupling of innovative technologies has emerged as a smart alternative for the process intensification of bioactive compound extraction from plant matrices. In this regard, the development of hybridized techniques based on the low-frequency and high-power ultrasound and high-pressure technologies, such as supercritical fluid extraction, pressurized liquids extraction, and gas-expanded liquids extraction, can enhance the recovery yields of phytochemicals due to their different action mechanisms. Therefore, this paper reviewed and discussed the current scenario in this field where ultrasound-related technologies are coupled with high-pressure techniques. The main findings, gaps, challenges, advances in knowledge, innovations, and future perspectives were highlighted. Full article
(This article belongs to the Special Issue Advances in Ultrasound Chemistry)
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