Symmetry and Asymmetry in Medicinal Chemistry

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: 30 June 2024 | Viewed by 10806

Special Issue Editor


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Guest Editor
1. Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Bratislava, Slovakia
2. Regional Centre of Advanced Technologies and Materials, Palacky University, Olomouc, Czech Republic
Interests: medicinal chemistry; drug design; structure–activity relationships; pharmaceutical analysis; ADME; nanoparticles; nanoformulations; controlled/targeted delivery
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Special Issue Information

Dear Colleagues,

Symmetry, and, on the other hand, asymmetry (chirality), is one of the most important phenomena in nature, causing the uniqueness of life and life processes. Chirality is caused by a so-called chirality element in the structure of a molecule, which can be center (chiral atom), axis (with limited rotation around a simple bond), or plane. Any organism can be considered a chiral environment, and due to this phenomenon, it is possible to specifically influence the binding of biologically active compounds to their target sites, if their effect depends on the specific binding to the target organ.

The effect of diastereoisomers and even individual enantiomers can be completely different or even toxic. For this reason, in the last few decades, increased attention has been paid to the investigation of these optically active forms both in terms of binding to target sites and the detailed knowledge of the mechanism of action, including the structure of target sites and pharmacokinetic profile, i.e., bioavailability for target sites and affinity for metabolism at the formation of potentially toxic chiral metabolites.

This Special Issue “Symmetry and Asymmetry in Medicinal Chemistry” of the journal Symmetry will focus on recent activities in the investigation of bioactive compounds in all areas of medicinal chemistry. Therefore, we are looking for contributions (research and review articles) covering a wide range of topics on the asymmetry of bioactive compounds, including (though not limited to) the following:

  • Asymmetric synthesis
  • Chiral separation
  • Analytical techniques suitable for the study of chiral compounds
  • Structural characterization of receptors, enzymes, and other chiral targets of bioactive agents
  • In silico study of chiral compounds
  • In vitro/in vivo studies of chiral compounds
  • Role of asymmetry in nanosciences
  • Legislation and guidelines relating to the issue of chirality

Submit your paper and select the Journal “Symmetry” and the Special Issue “Symmetry and Asymmetry in Medicinal Chemistry” via: MDPI submission system. Our papers will be published on a rolling basis and we will be pleased to receive your submission once you have finished it.

Prof. Dr. Josef Jampilek
Guest Editor

Manuscript Submission Information

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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. Symmetry is an international peer-reviewed open access monthly 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 2400 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

  • Chirality
  • Drugs
  • Natural compounds
  • Synthesis
  • Analysis
  • Pharmacophore
  • Targets
  • In silico/in vitro/in vivo studies
  • Asymmetry in nanosciences
  • Legislation and guidelines
  • Chemical biology

Published Papers (5 papers)

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Research

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8 pages, 957 KiB  
Article
An Effective Method for the Evaluation of the Enantiomeric Purity of 1,2-Diacyl-sn-glycero-3-phosphocholine-Based Lipids by NMR Analysis
by Antonia Di Mola, Lorenzo de Ferra, Mauro Anibaldi, Guglielmo Monaco and Antonio Massa
Symmetry 2024, 16(5), 624; https://doi.org/10.3390/sym16050624 - 17 May 2024
Viewed by 381
Abstract
In this article, we report a very efficient method for the determination of the enantiopurity of 1,2-diacyl-sn-glycero-3-phosphocholine by 1H NMR analysis using a readily available chiral derivatizing boronic acid (CDA), (R)-(2-(((1-phenylethyl)amino)methyl)phenyl)boronic acid. After the removal of the acyl [...] Read more.
In this article, we report a very efficient method for the determination of the enantiopurity of 1,2-diacyl-sn-glycero-3-phosphocholine by 1H NMR analysis using a readily available chiral derivatizing boronic acid (CDA), (R)-(2-(((1-phenylethyl)amino)methyl)phenyl)boronic acid. After the removal of the acyl groups of 1,2-diacyl-sn-glycero-3-phosphocholine via methanolysis and washing fatty acid byproducts with CHCl3, the obtained sn-glycero-3-phosphocholine (GPC) with the free diol moiety is derivatized by the chiral boronic acid and analyzed by 1H NMR analysis. The choline methyl resonance of each diastereomer is observed at distinctive chemical shifts in the 1H NMR spectrum. Integration of the respective resonances allows direct determination of the enantiomeric purity. The procedure was tested successfully using 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) with different enantiomeric purities and with commercially available 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC). Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Medicinal Chemistry)
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14 pages, 6277 KiB  
Article
Conformational and Chiroptical Properties of Salicylamide-Based Peptidomimetics
by Ivan Raich, Karel Pauk, Ales Imramovsky and Josef Jampílek
Symmetry 2024, 16(2), 138; https://doi.org/10.3390/sym16020138 - 24 Jan 2024
Viewed by 778
Abstract
Optical rotation (OR), the most frequently used chiroptical method, is used for the characterization of newly synthesized or isolated compounds. Computational predictions of OR are, however, mainly used for the determination of the absolute configurations of chiral compounds, but they may also be [...] Read more.
Optical rotation (OR), the most frequently used chiroptical method, is used for the characterization of newly synthesized or isolated compounds. Computational predictions of OR are, however, mainly used for the determination of the absolute configurations of chiral compounds, but they may also be used for the verification of conformational analysis results if the experimental values are known. Our computational study deals with the conformational analysis of flexible salicylamide-based peptidomimetics, starting with a conformation search, then a low-level ab initio preoptimization of the hundreds of conformations found, and, finally, a higher-level DFT optimization. For the resulting minima structures, Boltzmann populations were calculated, followed by OR calculations for all the populated conformers using the DFT method with various basis sets with diffuse functions. Weighted averages of the ORs were compared with experimental values, and the agreement, which ranged from excellent to moderate for various compounds, served as a verification of the conformational analysis results. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Medicinal Chemistry)
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21 pages, 5210 KiB  
Article
The Effect of the Stationary Phase on Resolution in the HPLC-Based Separation of Racemic Mixtures Using Vancomycin as a Chiral Selector: A Case Study with Profen Nonsteroidal Anti-Inflammatory Drugs
by Dehbiya Gherdaoui, Madiha Melha Yahoum, Selma Toumi, Hichem Tahraoui, Fatma Bouazza, Sonia Lefnaoui, Abdelhamid Zeghdaoui, Abdeltif Amrane, Bassem Jaouadi and Jie Zhang
Symmetry 2023, 15(12), 2154; https://doi.org/10.3390/sym15122154 - 4 Dec 2023
Viewed by 1062
Abstract
Chiral resolution is a technique of choice, making it possible to obtain asymmetric and enantiomerically pure compounds from a racemic mixture. This study investigated the behavior of vancomycin when used as a chiral additive in high-performance liquid chromatography (HPLC) to separate enantiomers of [...] Read more.
Chiral resolution is a technique of choice, making it possible to obtain asymmetric and enantiomerically pure compounds from a racemic mixture. This study investigated the behavior of vancomycin when used as a chiral additive in high-performance liquid chromatography (HPLC) to separate enantiomers of nonsteroidal anti-inflammatory drugs (NSAIDs), including ketoprofen, ibuprofen, flurbiprofen, and naproxen enantiomeric impurities. We compared two achiral stationary phases (C18 and NH2) to assess the impact of mobile phase composition and stationary phase on the vancomycin retention time in the racemic resolution of drug enantiomers. Our results demonstrated the successful enantioseparation of all drugs using vancomycin in the mobile phase (phosphate buffer 0.05 M/2-propanol, 50/50) with an NH2 column. This enhanced separation on the NH2 column resulted from the chromatography system’s efficiency and vancomycin dimers’ stereoselective interaction on the NH2 surface. This study underscores the importance of stationary phase selection in the chiral resolution of NSAIDs with vancomycin as a chiral additive. It offers valuable insights for future research and development of NSAID chiral separation methods, highlighting potential vancomycin applications in this context. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Medicinal Chemistry)
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14 pages, 7727 KiB  
Article
Crystal Structure of Chiral Drug Prenalterol and Its Precursor Prone to Spontaneous Resolution
by Alexander A. Bredikhin, Robert R. Fayzullin and Zemfira A. Bredikhina
Symmetry 2022, 14(6), 1150; https://doi.org/10.3390/sym14061150 - 2 Jun 2022
Cited by 4 | Viewed by 1862
Abstract
Due to the chiral uniformity of proteins and carbohydrates, the basic building blocks of living matter, the mirror symmetry characteristics of drugs are of exceptional importance for medicinal chemistry. In this work, we present a new synthesis of the mono-enantiomeric chiral drug prenalterol [...] Read more.
Due to the chiral uniformity of proteins and carbohydrates, the basic building blocks of living matter, the mirror symmetry characteristics of drugs are of exceptional importance for medicinal chemistry. In this work, we present a new synthesis of the mono-enantiomeric chiral drug prenalterol 1 based on the symmetry-breaking phenomenon, namely, the spontaneous resolution of 4-hydroxyphenyl glycerol ether 2. The single crystal X-ray diffraction method was used to investigate both rac- and (S)-1 as well as (R)-2. A feature of the main crystal-forming supramolecular motif (SMM) for diol 2 is the participation of three different molecules representing different types of hydroxyl groups in the formation of its repeating unit. The type of prenalterol SMM, as in the case of the related drugs propranolol 3 and pindolol 4, appears to be a chirality driven property, and is dictated by the enantiomeric composition of the crystals. In single-enantiomeric forms, infinite one-dimensional chains are realized, organized around helical axes, while in racemates, zero-dimensional cycles are realized, organized around inversion symmetry elements. The results obtained again demonstrate the influence of the chiral polarization of a substance not only on the general (selection of a space group), but also on particular characteristics of matter crystal organization, namely selection of a specific SMM. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Medicinal Chemistry)
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Review

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16 pages, 1445 KiB  
Review
Chirality and the Origin of Life
by Ferdinand Devínsky
Symmetry 2021, 13(12), 2277; https://doi.org/10.3390/sym13122277 - 30 Nov 2021
Cited by 23 | Viewed by 5218
Abstract
The origin of life, based on the homochirality of biomolecules, is a persistent mystery. Did life begin by using both forms of chirality, and then one of the forms disappeared? Or did the choice of homochirality precede the formation of biomolecules that could [...] Read more.
The origin of life, based on the homochirality of biomolecules, is a persistent mystery. Did life begin by using both forms of chirality, and then one of the forms disappeared? Or did the choice of homochirality precede the formation of biomolecules that could ensure replication and information transfer? Is the natural choice of L-amino acids and D-sugars on which life is based deterministic or random? Is the handedness present in/of the Universe from its beginning? The whole biosystem on the Earth, all living creatures are chiral. Many theories try to explain the origin of life and chirality on the Earth: e.g., the panspermia hypothesis, the primordial soup hypothesis, theory of parity violation in weak interactions. Additionally, heavy neutrinos and the impact of the fact that only left-handed particles decay, and even dark matter, all have to be considered. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Medicinal Chemistry)
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