molecules-logo

Journal Browser

Journal Browser

Cyclodextrin Chemistry 2018

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

Deadline for manuscript submissions: closed (15 March 2019) | Viewed by 75516

Special Issue Editor


E-Mail Website
Guest Editor
University of Lille, UMET CNRS8207, 59655 Villeneuve d'Ascq, France
Interests: polymerization; polymers; polymeric materials; polymer synthesis; polymer science; material characterization; biomaterials; hybrid materials; polymeric biomaterials; biopolymers
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrins (CDs) are a family starch derivates discovered by Villiers in 1891, of which a cyclic structure was evidenced in the 1930s by Freudenberg, followed by the exploration of their remarkable encapsulation properties from the 1950–1970. Cyclodextrins applications have, thereafter, increased, involving many academic and industrial researchers who have published up to 40,000 papers (including more than 2000 in 2016) and almost 800 patents (Scopus source) up to now. Studies and applications firstly focused on "native" alpha/beta/gamma-cyclodextrins, but chemists have rapidly tuned their properties through chemical modifications with substituent groups, polymerization reactions, and materials surfaces modifications. Furthermore, the versatility of cyclodextrins was still extended thanks to the emergence of nanotechnologies. This "modern period" has paved the way for increasing application fields of cyclodextrins, such as biotechnologies, soil remediation, wastewaters treatment, analytical chemistry, drug vectorization and drug delivery, pharmaceutical excipients, flavor and fragrance stabilization, controlled release, biomaterials, homogeneous, biphasis and heterogeneous catalysis, self-healing materials, etc. Such versatile properties of cyclodextrins explain why cyclodextrins have attracted a great deal of interest in a variety of industries, including those related to food, pharmaceuticals, cosmetics, chemicals, and agriculture. This Special Issue on cyclodextrin chemistry aims to provide a forum for the dissemination of the latest information on new chemical methods for access to advanced cyclodextrins-based systems, useable in the aforementioned application domains and industries.

Prof. Dr. Bernard Martel
Guest Editor

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

  • cyclodextrins in advanced materials
  • cyclodextrins based stimuli-responsive systems
  • green chemistry processes based on cyclodextrins
  • cyclodextrins based catalysts
  • syntheses of cyclodextrins derivates and polymers
  • applications of cyclodextrins in food
  • cyclodextrins-based hydrogels
  • cosmetic formulations
  • cyclodextrin for vectorization and/or controled release of active substances
  • cyclodextrins involved in environmental depollution (air, soils, waste waters, sediments)
  • nano materials and nano-structured coatings containing cyclodextrins

Related Special Issue

Published Papers (12 papers)

Order results
Result details
Select all
Export citation of selected articles as:

Research

Jump to: Review, Other

15 pages, 1946 KiB  
Article
Effect of the Incorporation of Functionalized Cyclodextrins in the Liposomal Bilayer
by Romina Zappacosta, Benedetta Cornelio, Serena Pilato, Gabriella Siani, François Estour, Massimiliano Aschi and Antonella Fontana
Molecules 2019, 24(7), 1387; https://doi.org/10.3390/molecules24071387 - 09 Apr 2019
Cited by 13 | Viewed by 3483
Abstract
Liposomes loaded with drug–cyclodextrin complexes are widely used as drug delivery systems, especially for species with low aqueous solubility and stability. Investigation of the intimate interactions of macrocycles with liposomes are essential for formulation of efficient and stable drug-in-cyclodextrin-in-liposome carriers. In this work, [...] Read more.
Liposomes loaded with drug–cyclodextrin complexes are widely used as drug delivery systems, especially for species with low aqueous solubility and stability. Investigation of the intimate interactions of macrocycles with liposomes are essential for formulation of efficient and stable drug-in-cyclodextrin-in-liposome carriers. In this work, we reported the preparation of unilamellar vesicles of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) embedded with native β-cyclodextrin and two synthetic derivatives: heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMCD) and heptakis(2,3-di-O-acetyl)-β-cyclodextrin (DACD). We then studied the effect of these macrocycles on the liposomal size, membrane viscosity, and liposomal stability at different temperatures and concentrations. We observed that TMCD and DACD affected vesicle size and the change of size was related to CD concentration. Irrespective of its nature, the macrocycle established interactions with the phospholipidic head groups, preventing cyclodextrins to diffuse into the lipid bilayer, as confirmed by molecular dynamics simulations. Such supramolecular structuring improves liposome stability making these colloid systems promising carriers for biologically active compounds. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

13 pages, 3018 KiB  
Article
Molecular Simulation of the Separation of Isoleucine Enantiomers by β-Cyclodextrin
by Elena Alvira
Molecules 2019, 24(6), 1021; https://doi.org/10.3390/molecules24061021 - 14 Mar 2019
Cited by 13 | Viewed by 2870
Abstract
Molecular mechanics and dynamics simulations were carried out to study the capacity of isoleucine enantiomers to form inclusion complexes with β–cyclodextrin, and to be discriminated by this chiral compound, in vacuo and with different solvents. Solvents were characterized not only by the value [...] Read more.
Molecular mechanics and dynamics simulations were carried out to study the capacity of isoleucine enantiomers to form inclusion complexes with β–cyclodextrin, and to be discriminated by this chiral compound, in vacuo and with different solvents. Solvents were characterized not only by the value of dielectric constant ε in the Coulombic interaction energy, but also by the neutral and zwitterion configurations of isoleucine. Whereas the discrimination between the enantiomers for ε ≤ 2 is due to the electrostatic contribution, these differences are mainly due to the Lennard-Jones potential for ε > 2. The most enantioselective regions are located near the cavity walls, independently of the solvent. D-Ile is more stable than L-Ile in broader regions in vacuo, but L-Ile presents more stable locations with water. Isoleucine can form inclusion complexes with β–cyclodextrin in vacuo and with different solvents. Two probable configurations are deduced from the molecular dynamics simulation, in which the guest is always inside the cavity and with the carboxylic end of the amino acid oriented towards either rim of β–CD. In the simulation, the enantiomers preferentially occupy regions with greater chiral discrimination. The first eluted enantiomer in vacuo and with different solvents is L-Ile, independently of the solvent polarity. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

15 pages, 2957 KiB  
Article
Mannosylated Polyrotaxanes for Increasing Cellular Uptake Efficiency in Macrophages through Receptor-Mediated Endocytosis
by Kai Shibaguchi, Atsushi Tamura, Masahiko Terauchi, Mitsuaki Matsumura, Hiroyuki Miura and Nobuhiko Yui
Molecules 2019, 24(3), 439; https://doi.org/10.3390/molecules24030439 - 26 Jan 2019
Cited by 18 | Viewed by 4067
Abstract
Macrophages play an important role in the regulation of inflammation and immune response as well as the pathogenesis of chronic inflammatory diseases and cancer. Therefore, targeted delivery of therapeutic reagents to macrophages is an effective method for treatment and diagnosis. We previously examined [...] Read more.
Macrophages play an important role in the regulation of inflammation and immune response as well as the pathogenesis of chronic inflammatory diseases and cancer. Therefore, targeted delivery of therapeutic reagents to macrophages is an effective method for treatment and diagnosis. We previously examined the therapeutic applications of polyrotaxanes (PRXs) comprised of multiple cyclodextrins (CDs) threaded on a polymer chain and capped with bulky stopper molecules. In the present study, we designed an α-d-mannose-modified α-CD/poly(ethylene glycol)-based PRX (Man-PRX). The intracellular uptake of Man-PRX through the interaction with macrophage mannose receptor (MMR) in macrophage-like RAW264.7 cells was examined. Intracellular Man-PRX uptake was observed in MMR-positive RAW264.7 cells but was negligible in MMR-negative NIH/3T3 cells. In addition, the intracellular Man-PRX uptake in RAW264.7 cells was significantly inhibited in the presence of free α-d-mannose and an anti-MMR antibody, which suggests that MMR is involved in the intracellular uptake of Man-PRX. Moreover, the polarization of RAW264.7 cells affected the Man-PRX internalization efficiency. These results indicate that Man-PRX is an effective candidate for selective targeting of macrophages through a specific interaction with the MMR. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

16 pages, 5552 KiB  
Article
Characterization and Antiproliferative Activity of a Novel 2-Aminothiophene Derivative-β-Cyclodextrin Binary System
by Elayne Barros Ferreira, Walter Ferreira Da Silva Júnior, Jonas Gabriel De Oliveira Pinheiro, Aldilane Gonçalves Da Fonseca, Telma Maria Araújo Moura Lemos, Hugo Alexandre De Oliveira Rocha, Eduardo Pereira De Azevedo, Francisco Jaime Bezerra Mendonça Junior and Ádley Antonini Neves de Lima
Molecules 2018, 23(12), 3130; https://doi.org/10.3390/molecules23123130 - 29 Nov 2018
Cited by 11 | Viewed by 2749
Abstract
The novel 2-aminothiophene derivative 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN) has shown potential anti-proliferative activity in human cancer cell lines. However, the poor aqueous solubility of 6CN impairs its clinical use. This work aimed to develop binary 6CN-β-cyclodextrin (βCD) systems with the purpose of increasing [...] Read more.
The novel 2-aminothiophene derivative 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN) has shown potential anti-proliferative activity in human cancer cell lines. However, the poor aqueous solubility of 6CN impairs its clinical use. This work aimed to develop binary 6CN-β-cyclodextrin (βCD) systems with the purpose of increasing 6CN solubility in water and therefore, to improve its pharmacological activity. The 6CN-βCD binary systems were prepared by physical mixing, kneading and rotary evaporation methods and further characterized by FTIR, XRD, DSC, TG and SEM. In addition, molecular modeling and phase solubility studies were performed. Finally, MTT assays were performed to investigate the cytostatic and anti-proliferative effects of 6CN-βCD binary systems. The characterization results show evident changes in the physicochemical properties of 6CN after the formation of the binary systems with βCD. In addition, 6CN was associated with βCD in aqueous solution and the solid state, which was confirmed by molecular modeling and the aforementioned characterization techniques. Phase solubility studies indicated that βCD forms stable 1:1 complexes with 6CN. The MTT assay demonstrated the cytostatic and anti-proliferative activities of 6CN-βCD binary systems and therefore, these might be considered as promising candidates for new anticancer drugs. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

17 pages, 6345 KiB  
Article
A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation
by David Mathiron, Renato Iori, Serge Pilard, Thangavelu Soundara Rajan, David Landy, Emanuela Mazzon, Patrick Rollin and Florence Djedaïni-Pilard
Molecules 2018, 23(7), 1714; https://doi.org/10.3390/molecules23071714 - 13 Jul 2018
Cited by 17 | Viewed by 4238
Abstract
Moringin, obtained via enzymatic conversion of the glucosinolate precursor glucomoringin, is an uncommon member of the isothiocyanate class, and has been proven to possess a broad range of biological activities such as antitumor activity, protection against neurodegenerative disorders and bactericidal effects. Since moringin [...] Read more.
Moringin, obtained via enzymatic conversion of the glucosinolate precursor glucomoringin, is an uncommon member of the isothiocyanate class, and has been proven to possess a broad range of biological activities such as antitumor activity, protection against neurodegenerative disorders and bactericidal effects. Since moringin is weakly soluble in water and unstable in aqueous medium, cyclodextrins (CDs) were considered for the development of a new moringin formulation, with a view to improving its solubility and stability in aqueous solution for use as an anti-inflammatory. A combined structural study using proton nuclear magnetic resonance (1H-NMR), diffusion-ordered spectroscopy (DOSY) and ion mobility mass spectrometry (IM-MS) is reported, highlighting the formation of a 1:1 α-CD/moringin inclusion complex. The association constant K was determined (1300 M−1 at 300 K). Completion of the structural characterization was performed by T-ROESY and MS/MS experiments, which evidenced the mode of penetration of moringin into α-CD. Finally, the “chaperone-like” properties of α-CD with respect to the stability of moringin have been highlighted. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

9 pages, 1166 KiB  
Article
Controlled Release of DEET Loaded on Fibrous Mats from Electrospun PMDA/Cyclodextrin Polymer
by Claudio Cecone, Fabrizio Caldera, Francesco Trotta, Pierangiola Bracco and Marco Zanetti
Molecules 2018, 23(7), 1694; https://doi.org/10.3390/molecules23071694 - 11 Jul 2018
Cited by 17 | Viewed by 3410
Abstract
Electrospun beta-cyclodextrin (βCD)-based polymers can combine a high surface-to-volume ratio and a high loading/controlled-release-system potential. In this work, pyromellitic dianhydride (PMDA)/βCD-based nanosponge microfibers were used to study the capability to host a common insect repellent (N,N-diethyl-3-toluamide (DEET)) and to [...] Read more.
Electrospun beta-cyclodextrin (βCD)-based polymers can combine a high surface-to-volume ratio and a high loading/controlled-release-system potential. In this work, pyromellitic dianhydride (PMDA)/βCD-based nanosponge microfibers were used to study the capability to host a common insect repellent (N,N-diethyl-3-toluamide (DEET)) and to monitor its release over time. Fibrous samples characterized by an average fibrous diameter of 2.8 ± 0.8 µm were obtained and subsequently loaded with DEET, starting from a 10 g/L diethyl ether (DEET) solution. The loading capacity of the system was assessed via HPLC/UV–Vis analysis and resulted in 130 mg/g. The releasing behavior was followed by leaving fibrous DEET-loaded nanosponge samples in air at room temperature for a period of between 24 h and 2 weeks. The releasing rate and the amount were calculated by thermogravimetric analysis (TGA), and the release of the repellent was found to last for over 2 weeks. Eventually, both the chemical composition and sample morphology were proven to play a key role for the high sample loading capacity, determining the microfibers’ capability to be applied as an effective controlled-release system. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Figure 1

16 pages, 4847 KiB  
Article
A Novel Cyclodextrin-Functionalized Hybrid Silicon Wastewater Nano-Adsorbent Material and Its Adsorption Properties
by Jing Li, Chao Qiu, Haoran Fan, Yuxiang Bai, Zhengyu Jin and Jinpeng Wang
Molecules 2018, 23(6), 1485; https://doi.org/10.3390/molecules23061485 - 19 Jun 2018
Cited by 8 | Viewed by 3536
Abstract
A novel cyclodextrin-functionalized hybrid silicon nano-adsorbent material (6-EA-β-CD-Si) was synthesized via the nucleophilic substitution method. The structure was detected by Fourier transform infrared (FT-IR), X-ray, thermogravimetric analysis, and Brunauer-Emmett-Teller (BET) analysis. Results reveal that the BET surface area of 6-EA-β-CD-Si is 240 m [...] Read more.
A novel cyclodextrin-functionalized hybrid silicon nano-adsorbent material (6-EA-β-CD-Si) was synthesized via the nucleophilic substitution method. The structure was detected by Fourier transform infrared (FT-IR), X-ray, thermogravimetric analysis, and Brunauer-Emmett-Teller (BET) analysis. Results reveal that the BET surface area of 6-EA-β-CD-Si is 240 m2/g and the average pore size is 4.16 nm. The adsorption properties of 6-EA-β-CD-Si onto methylene blue (MB) were studied and fitted with adsorption kinetic models. Both the Freundlich adsorption isotherm model and pseudo-second-order model were fitted with well shows that the multi-layer adsorption with chemisorption and physisorption co-existing in the system. The maximum adsorption capacities are 39.37, 39.21, 36.90, and 36.36 mg/g at temperatures 303, 313, 323, and 333 K, respectively. The maximum removal rate of MB could reach 99.5%, indicating the potential application value of 6-EA-β-CD-Si in wastewater treatment. The adsorption mechanisms of 6-EA-β-CD-Si showed that the hydrophobic cave of β-CD plays an important role on the adsorption of MB. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

14 pages, 2318 KiB  
Article
Hydroxypropyl-β-cyclodextrin for Delivery of Baicalin via Inclusion Complexation by Supercritical Fluid Encapsulation
by Ying Li, Zhen-Dan He, Qian-En Zheng, Chengshen Hu and Wing-Fu Lai
Molecules 2018, 23(5), 1169; https://doi.org/10.3390/molecules23051169 - 14 May 2018
Cited by 19 | Viewed by 4154
Abstract
Over the years, various methods have been developed to enhance the solubility of insoluble drugs; however, most of these methods are time-consuming and labor intensive or involve the use of toxic materials. A method that can safely and effectively enhance the solubility of [...] Read more.
Over the years, various methods have been developed to enhance the solubility of insoluble drugs; however, most of these methods are time-consuming and labor intensive or involve the use of toxic materials. A method that can safely and effectively enhance the solubility of insoluble drugs is lacking. This study adopted baicalin as an insoluble drug model, and used hydroxypropyl-β-cyclodextrin for the delivery of baicalin via the inclusion complexation by supercritical fluid encapsulation. Different parameters for the complex preparation as well as the physicochemical properties of the complex have been investigated. Our results showed that when compared to the conventional solution mixing approach, supercritical fluid encapsulation enables a more precise control of the properties of the complex, and gives higher loading and encapsulation efficiency. It is anticipated that our reported method can be useful in enhancing the preparation efficiency of inclusion complexes, and can expand the application potential of insoluble herbal ingredients in treatment development and pharmaceutical formulation. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

Review

Jump to: Research, Other

18 pages, 1089 KiB  
Review
Cyclodextrin-Enabled Polymer Composites for Packaging
by Lajos Szente and Éva Fenyvesi
Molecules 2018, 23(7), 1556; https://doi.org/10.3390/molecules23071556 - 27 Jun 2018
Cited by 53 | Viewed by 6489
Abstract
Cyclodextrin complexes of fragrances, antimicrobial agents, dyes, insecticides, UV-filters can be incorporated into polymers (packaging films, trays, containers) either to ensure the slow release or a homogeneous distribution of the complexed substances. This way the propagation of microorganisms on surface of enwrapped products [...] Read more.
Cyclodextrin complexes of fragrances, antimicrobial agents, dyes, insecticides, UV-filters can be incorporated into polymers (packaging films, trays, containers) either to ensure the slow release or a homogeneous distribution of the complexed substances. This way the propagation of microorganisms on surface of enwrapped products is decelerated, or the product is made more attractive by slowly released fragrances, protected against UV-light-induced deterioration, oxidation, etc. Incorporating empty cyclodextrins into the packaging material an aroma barrier packaging is produced, which decelerates the loss of the aroma from the packaged food, prevents the penetration of undesired volatile pollutants from the environment, like components of exhaust gases, cigarette smoke, and reduces the migration of plasticizers, residual solvents and monomers, etc. Applying cyclodextrins in active packaging allows to preserve the quality of food and ensures a longer shelf-life for the packaged items. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

23 pages, 2114 KiB  
Review
Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review
by Miriana Kfoury, David Landy and Sophie Fourmentin
Molecules 2018, 23(5), 1204; https://doi.org/10.3390/molecules23051204 - 17 May 2018
Cited by 114 | Viewed by 10938
Abstract
Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion [...] Read more.
Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion complexes. Such a property is interestingly employed to retain volatile guests and reduce their volatility. Within this scope, the starting crucial point for a suitable and careful characterization of an inclusion complex is to assess the value of the formation constant (Kf), also called stability or binding constant. This task requires the application of the appropriate analytical method and technique. Thus, the aim of the present paper is to give a general overview of the main analytical tools used for the determination of Kf values for CD/volatile inclusion complexes. This review emphasizes on the advantages, inconvenients and limits of each applied method. A special attention is also dedicated to the improvement of the current methods and to the development of new techniques. Further, the applicability of each technique is illustrated by a summary of data obtained from the literature. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Figure 1

15 pages, 1197 KiB  
Review
Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes
by Phennapha Saokham, Chutimon Muankaew, Phatsawee Jansook and Thorsteinn Loftsson
Molecules 2018, 23(5), 1161; https://doi.org/10.3390/molecules23051161 - 11 May 2018
Cited by 403 | Viewed by 22860
Abstract
Cyclodextrins (CDs), a group of oligosaccharides formed by glucose units bound together in a ring, show a promising ability to form complexes with drug molecules and improve their physicochemical properties without molecular modifications. The stoichiometry of drug/CD complexes is most frequently 1:1. However, [...] Read more.
Cyclodextrins (CDs), a group of oligosaccharides formed by glucose units bound together in a ring, show a promising ability to form complexes with drug molecules and improve their physicochemical properties without molecular modifications. The stoichiometry of drug/CD complexes is most frequently 1:1. However, natural CDs have a tendency to self-assemble and form aggregates in aqueous media. CD aggregation can limit their solubility. Through derivative formation, it is possible to enhance their solubility and complexation capacity, but this depends on the type of substituent and degree of substitution. Formation of water-soluble drug/CD complexes can increase drug permeation through biological membranes. To maximize drug permeation the amount of added CD into pharmaceutical preparation has to be optimized. However, solubility of CDs, especially that of natural CDs, is affected by the complex formation. The presence of pharmaceutical excipients, such as water-soluble polymers, preservatives, and surfactants, can influence the solubilizing abilities of CDs, but this depends on the excipients’ physicochemical properties. The competitive CD complexation of drugs and excipients has to be considered during formulation studies. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

Other

Jump to: Research, Review

11 pages, 3328 KiB  
Concept Paper
Development of Dipicolylamine-Modified Cyclodextrins for the Design of Selective Guest-Responsive Receptors for ATP
by Tatsuru Yamada, Shoji Fujiwara, Kyohhei Fujita, Yuji Tsuchido, Takeshi Hashimoto and Takashi Hayashita
Molecules 2018, 23(3), 635; https://doi.org/10.3390/molecules23030635 - 12 Mar 2018
Cited by 15 | Viewed by 5541
Abstract
The construction of supramolecular recognition systems based on specific host–guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent [...] Read more.
The construction of supramolecular recognition systems based on specific host–guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent indicator. We synthesized dipicolylamine (DPA)-modified CyD–Cu2+ complexes (Cu·1α, Cu·1β, and Cu·1γ), and evaluated their recognition capabilities toward phosphoric acid derivatives in water. The UV-Vis absorption and fluorescence spectra revealed that Cu·1β selectively recognized ATP over other organic and inorganic phosphates, and that β-CyD had the most suitable cavity size for complexation with ATP. The 1D and 2D NMR analyses suggested that the ATP recognition was based on the host–guest interaction between the adenine moiety of ATP and the CyD cavity, as well as the recognition of phosphoric moieties by the Cu2+–DPA complex site. The specific interactions between the CyD cavity and the nucleobases enabled us to distinguish ATP from other nucleoside triphosphates, such as guanosine triphosphate (GTP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). This study clarified the basic mechanisms of molecular recognition by modified CyDs, and suggested the potential for further application of CyDs in the design of highly selective supramolecular recognition systems for certain molecular targets in water. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
Show Figures

Graphical abstract

Back to TopTop