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Macrocycles as Catalysts and Drug Carriers
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Macrocycles as Catalysts and Drug Carriers

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Biochemistry".

Deadline for manuscript submissions: closed (31 March 2021) | Viewed by 12388

Special Issue Editors

Prof. Dr. Grigory V. Zyryanov

E-Mail Website
Guest Editor
1. I.Ya. Postovsky Insititute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences (IOS UB RAS), 620137 Ekaterinburg, Russia
2. Department of Organic and Biomolecular Chemistry, Ural Federal University, 620062 Ekaterinburg, Russia
Interests: fluorophores; chemosensors; ligands; drug candidates; fluorescence; luminescent lanthanide complexes; luminescence
Special Issues, Collections and Topics in MDPI journals
Dr. Sougata Santra

E-Mail Website
Guest Editor
Department of Organic & Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Yekaterinburg, Russia
Interests: green chemistry; (aza)pyridines; lantahanide chelates; CH-functionalization; (hetero)macrocycles; molecular recognition; drug candidates
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Naturally occurring and synthetic macrocyclic compounds possess tunable physic-chemical properties as well as intriguing host–guest properties which are controlled by both peripheral substitution and inner cavity size. Progress in the synthesis and fundamental understanding of host–guest properties has led to significant advances in the creation of macrocycle-based materials for various medicinal and catalytic applications.

For these applications, it is important to design and synthesize macrocycles which have great potential to interact with both various biological targets and organic/inorganic molecules, architectures, or metal NPs through supramolecular (self-)assembly by means of noncovalent interactions including encapsulation, hydrogen bonding, pi-stacking, and electrostatic interactions.

In this respect, new macrocycles and macrocycle-based materials with the ability to support, transport, and release drug molecules, macrocycles, and materials for bioimaging and theranostics as well as macrocycles with the ability to support various catalysts for catalyzing chemical reactions are attracting the increasing interest of the world scientific community.

This Special Issue welcomes the submission of original research papers or comprehensive reviews that describe significant advances in macrocyclic hosts, macrocyclic druglike molecules, or macrocycle-based hybrid materials and composites in terms of their applications as drug delivery systems, catalysts, materials for bioimaging or theranostic, nano(bio)materials for personal medicine, and other aspects.

Subtopics:

  1. Pre- and post-modification of macrocycles with ionic and nonionic groups for the enhanced encapsulation and/or controlled release of drugs and/or for improved catalytic activity
  2. Druglike (metallo)macrocycles
  3. Encapsulation and (photo)controlled release of therapeutic agents
  4. (Metallo)macrocyclic agents for photodynamic therapy
  5. Macrocycle-supported metal NPs for medicinal and catalytic applications
  6. Macrocycle-based nanocomposites for medicinal and catalytic applications
  7. (Photo)catalytic effects and (photo)catalytic activity

Prof. Dr. Zyryanov Grigoriy
Dr. Sougata Santra
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. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. 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
  • cucurbiturils
  • calixarenes
  • pillararenes
  • resorcinarenes
  • cycloparaphenylenes
  • (metallo)porphyrins/phthalocyanines
  • cyclic peptides
  • (element)crown ethers
  • (aza)pyridine-based macrocycles

Published Papers (5 papers)

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Research

19 pages, 4131 KiB  
Article
Cyclodextrins Allow the Combination of Incompatible Vancomycin and Ceftazidime into an Ophthalmic Formulation for the Treatment of Bacterial Keratitis
by Yassine Bouattour, Florent Neflot-Bissuel, Mounir Traïkia, Anne-Sophie Biesse-Martin, Robin Frederic, Mouloud Yessaad, Mireille Jouannet, Mathieu Wasiak, Philip Chennell and Valerie Sautou
Int. J. Mol. Sci. 2021, 22(19), 10538; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms221910538 - 29 Sep 2021
Cited by 2 | Viewed by 2027
Abstract
Ceftazidime (CZ) and vancomycin (VA) are two antibiotics used to treat bacterial keratitis. Due to their physical incompatibility (formation of a precipitate), it is not currently possible to associate both molecules in a single container for ophthalmic administration. We firstly characterized the incompatibility [...] Read more.
Ceftazidime (CZ) and vancomycin (VA) are two antibiotics used to treat bacterial keratitis. Due to their physical incompatibility (formation of a precipitate), it is not currently possible to associate both molecules in a single container for ophthalmic administration. We firstly characterized the incompatibility then investigated if 2-hydroxypropyl-beta (HPβCD) and 2-hydroxypropyl-gamma cyclodextrins (HPγCD) could prevent this incompatibility. The impact of pH on the precipitation phenomena was investigated by analysing the supernatant solution of the mixture using high performance liquid chromatography. A characterization of the inclusion of CZ with HPγCD using 1H nuclear magnetic resonance (NMR), and VA with HPβCD using 1H-NMR and a solubility diagram was performed. A design of experiment was built to determine the optimal conditions to obtain a formulation that had the lowest turbidity and particle count. Our results showed that VA and CZ form an equimolar precipitate below pH 7.3. The best formulation obtained underwent an in-vitro evaluation of its antibacterial activity. The impact of HPCDs on incompatibility has been demonstrated through the inclusion of antibiotics and especially VA. The formulation has been shown to be able to inhibit the incompatibility for pH higher than 7.3 and to possess unaltered antibacterial activity. Full article
(This article belongs to the Special Issue Macrocycles as Catalysts and Drug Carriers)
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16 pages, 2746 KiB  
Article
Ligand-Tuning of the Stability of Pd(II) Conjugates with Cyanocobalamin
by Dominika Porębska, Łukasz Orzeł, Dorota Rutkowska-Zbik, Grażyna Stochel and Rudi van Eldik
Int. J. Mol. Sci. 2021, 22(15), 7973; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms22157973 - 26 Jul 2021
Cited by 4 | Viewed by 1737
Abstract
Besides the well-known functions performed by vitamin B12 (CblCN) in biochemical processes of the human body, an increasing interest has been raised by the possibility of its use as a transmembrane drug carrier, capable, among others, of enhancing the accumulation of inorganic [...] Read more.
Besides the well-known functions performed by vitamin B12 (CblCN) in biochemical processes of the human body, an increasing interest has been raised by the possibility of its use as a transmembrane drug carrier, capable, among others, of enhancing the accumulation of inorganic cytostatics in cancer cells. The present study was aimed at determining the possibility of the formation of CblCN conjugates with Pd(II) complexes. A key aspect was their stability, which we attempted to tune by appropriate choice of ligands. Syntheses, spectroscopic analysis of postreaction systems and kinetic investigations of conjugate formation reactions, have been complemented by DFT modelling. The obtained results showed that ligand charge, geometry and electron affinity may have a significant impact on carrier binding and release leading to the activation of the Pd(II) complex. This provides a rationale to expect that with appropriate composition of the coordination sphere, it will be possible to extend the spectrum of less toxic inorganic chemotherapeutics. Full article
(This article belongs to the Special Issue Macrocycles as Catalysts and Drug Carriers)
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10 pages, 2586 KiB  
Article
Supramolecular Zn(II)-Dipicolylamine-Azobenzene-Aminocyclodextrin-ATP Complex: Design and ATP Recognition in Water
by Shohei Minagawa, Shoji Fujiwara, Takeshi Hashimoto and Takashi Hayashita
Int. J. Mol. Sci. 2021, 22(9), 4683; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms22094683 - 28 Apr 2021
Cited by 8 | Viewed by 2101
Abstract
Cyclodextrins (CyDs) are water-soluble host molecules possessing a nanosized hydrophobic cavity. In the realm of molecular recognition, this cavity is used not only as a recognition site but also as a reaction medium, where a hydrophobic sensor recognizes a guest molecule. Based on [...] Read more.
Cyclodextrins (CyDs) are water-soluble host molecules possessing a nanosized hydrophobic cavity. In the realm of molecular recognition, this cavity is used not only as a recognition site but also as a reaction medium, where a hydrophobic sensor recognizes a guest molecule. Based on the latter concept, we have designed a novel supramolecular sensing system composed of Zn(II)-dipicolylamine metal complex-based azobenzene (1-Zn) and 3A-amino-3A-deoxy-(2AS,3AS)-γ-cyclodextrin (3-NH2-γ-CyD) for sensing adenosine-5′-triphosphate (ATP). 1-Zn showed redshifts in the UV-Vis spectra and induced circular dichroism (ICD) only when both ATP and 3-NH2-γ-CyD were present. Calculations of equilibrium constants indicated that the amino group of 3-NH2-γ-CyD was involved in the formation of supramolecular 1-Zn/3-NH2-γ-CyD/ATP. The Job plot of the ICD spectral response revealed that the stoichiometry of 1-Zn/3-NH2-γ-CyD/ATP was 2:1:1. The pH effect was examined and 1-Zn/3-NH2-γ-CyD/ATP was most stable in the neutral condition. The NOESY spectrum suggested the localization of 1-Zn in the 3-NH2-γ-CyD cavity. Based on the obtained results, the metal coordination interaction of 1-Zn and the electrostatic interaction of 3-NH2-γ-CyD were found to take place for ATP recognition. The “reaction medium approach” enabled us to develop a supramolecular sensing system that undergoes multi-point interactions in water. This study is the first step in the design of a selective sensing system based on a good understanding of supramolecular structures. Full article
(This article belongs to the Special Issue Macrocycles as Catalysts and Drug Carriers)
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13 pages, 4220 KiB  
Article
Enhancing the Physiochemical Properties of Puerarin via L-Proline Co-Crystallization: Synthesis, Characterization, and Dissolution Studies of Two Phases of Pharmaceutical Co-Crystals
by Muhammad Inam, Lu Liu, Jian-Wei Wang, Ka-Xi Yu, Chi-Uyen Phan, Jie Shen, Wen-Hua Zhang, Guping Tang and Xiurong Hu
Int. J. Mol. Sci. 2021, 22(2), 928; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms22020928 - 18 Jan 2021
Cited by 12 | Viewed by 3194
Abstract
Puerarin (PUE) is a Chinese traditional medicine known to enhance glucose uptake into the insulin cells to downregulate the blood glucose levels in the treatment of type II diabetes. Nevertheless, the bioavailability of pristine PUE is limited due to its poor solubility and [...] Read more.
Puerarin (PUE) is a Chinese traditional medicine known to enhance glucose uptake into the insulin cells to downregulate the blood glucose levels in the treatment of type II diabetes. Nevertheless, the bioavailability of pristine PUE is limited due to its poor solubility and low intestinal permeability. In this work, we demonstrate that the solubility of PUE can be significantly enhanced via its co-crystallization with L-Proline (PRO). Two crystalline phases, namely, the solvate-free form [PUE][PRO] (I) and the solvated form [PUE]2[PRO]∙EtOH∙(H2O)2 (II) are isolated. These two phases are characterized by single-crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD), Fourier-transformed infrared (FT-IR) spectra, nuclear magnetic resonance (NMR), and thermogravimetric analysis in association with differential scanning calorimetry (TGA-DSC). The solubility and dissolution rate of both I and II in water, gastrointestinal tract at pH 1.2, and phosphate buffer at pH 6.8 indicates a nearly doubled increase as compared to the pristine PUE. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay of pristine PUE, I and II against murine colon cancer cell lines CT-26 and human kidney cell lines HEK-293 indicated that neither compound exhibits obvious cytotoxicity after 24 h. This work showcases that the readily available and biocompatible PRO can be a promising adjuvant to enhance the physicochemical properties of PUE toward orally administered drug formulation with improved pharmacokinetics. Full article
(This article belongs to the Special Issue Macrocycles as Catalysts and Drug Carriers)
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13 pages, 4574 KiB  
Article
On the Single-Crystal Structure of Tenofovir Alafenamide Mono-Fumarate: A Metastable Phase Featuring a Mixture of Co-Crystal and Salt
by Jian-Wei Wang, Lu Liu, Ka-Xi Yu, Hong-Zhen Bai, Jun Zhou, Wen-Hua Zhang, Xiurong Hu and Guping Tang
Int. J. Mol. Sci. 2020, 21(23), 9213; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21239213 - 03 Dec 2020
Cited by 2 | Viewed by 2567
Abstract
Tenofovir alafenamide (TAF) is a prodrug of tenofovir as a potent nucleotide reverse transcriptase inhibitor. It serves as the key component of Genvoya® for the first-line treatment of human immunodeficiency virus infection (HIV) and is the active component of Vemlidy® for [...] Read more.
Tenofovir alafenamide (TAF) is a prodrug of tenofovir as a potent nucleotide reverse transcriptase inhibitor. It serves as the key component of Genvoya® for the first-line treatment of human immunodeficiency virus infection (HIV) and is the active component of Vemlidy® for the treatment of chronic hepatitis B. Vemlidy® is also a monotherapeutic regimen formulated as TAF hemifumarate (1; TAF:fumarate = 2:1). In this work, we report for the first time the single-crystal structure of TAF fumarate hemihydrate (2, TAF:fumarate:H2O = 2:2:1). Compound 2 is initially documented as a salt in which one proton of the fumaric acid migrates to the amine group of the adenine moiety in TAF. It was recently proposed that ca. 20–30% proton is transferred to the N atom on the aromatic adenine backbone. We herein provide definitive single-crystal X-ray diffraction results to confirm that 2, though phase pure, is formed as a mixture of co-crystal (75%) and salt (25%). It features two pairs of TAF fumarates, wherein one of the four H atoms on the fumaric acid is transferred to the N atom of the adjacent adenine moiety while the other three carboxylates remain in their intrinsic acid form. Compound 2 is a metastable phase during the preparation of 1 and can be isolated by halting the reaction during the refluxing of TAF and fumaric acid in acetonitrile (MeCN). Our report complements the previous characterizations of TAF monofumarate, and its elusive structural patterns are finally deciphered. Full article
(This article belongs to the Special Issue Macrocycles as Catalysts and Drug Carriers)
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