Structural Symmetry and Asymmetry Implications in Development of Recent Pharmacy and Medicine

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 12852

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Department of Physical Chemistry, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University, Toruń, Poland
Interests: molecular modeling of aromatic systems; properties of fullerenes using HF; DFT methods
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Department of Physical Chemistry, Collegium Medicum Nicolaus Copernicus University, Bydgoszcz, Poland

Special Issue Information

Dear Colleagues,

Structural symmetry or asymmetry are one of the most fundamental properties of chemical compounds, which is often an important factor determining their chemical and biological activity. This property of compounds is diverse and can be considered at various levels of structural organization, starting from the phenomenon of chirality, which plays an important role in numerous biological compounds, such as proteins, saccharides and nucleic acids, the presence of centers, planes or axes off symmetry which determine the structure of numerous chemical systems like metal complexes of organic compounds, and crystal lattices of compounds exhibiting pharmacological potential up to nanomaterials. The investigation of structural correlations with biological activity of compounds has becomea large area of research in modern chemistry, pharmacy, and medicinal chemistry. Such a research field has important practical implications in the development of novel materials, targeted therapies, drug design, and others. The aim of this Special Issue is to highlight and overview structural symmetry and asymmetry implications in the development of modernchemistry, pharmacy, and medicinal chemistry. All types of papers, including comprehensive reviews on general areas, mini reviews on specialized subjects, accounts of own research work, full experimental or theoretical papers, short communications, technical notes, comments, and others are welcome for consideration.

Prof. Dr. Lorentz JÄNTSCHI
Dr. Beata Szefler
Dr. Przemysław Czeleń
Guest Editors

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Published Papers (4 papers)

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Editorial

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4 pages, 215 KiB  
Editorial
Introducing Structural Symmetry and Asymmetry Implications in Development of Recent Pharmacy and Medicine
by Lorentz Jäntschi
Symmetry 2022, 14(8), 1674; https://doi.org/10.3390/sym14081674 - 12 Aug 2022
Cited by 9 | Viewed by 1358
Abstract
Structural symmetry, anti-symmetry, or asymmetry represent a foundational property that, for chemical compounds, often determines their chemical and biological activity [...] Full article

Research

Jump to: Editorial

22 pages, 3802 KiB  
Article
Making and Breaking—Insight into the Symmetry of Salen Analogues
by Katarzyna M. Krupka, Sylwia Banach, Michał Pocheć, Jarosław J. Panek and Aneta Jezierska
Symmetry 2023, 15(2), 424; https://doi.org/10.3390/sym15020424 - 05 Feb 2023
Cited by 1 | Viewed by 1780
Abstract
This study focuses on selected members of the general salen-analogues family possessing two O-H⋯N hydrogen bonds, namely three isomers of N,N’-bis(salicylidene)-X-phenylenediamine, denoted as ortho, meta and para. Two of the isomers are not planar in the published crystal [...] Read more.
This study focuses on selected members of the general salen-analogues family possessing two O-H⋯N hydrogen bonds, namely three isomers of N,N’-bis(salicylidene)-X-phenylenediamine, denoted as ortho, meta and para. Two of the isomers are not planar in the published crystal structures. The current study tackles the problem of symmetry and interactions within the molecules, as well as in the crystal lattice. The aromaticity of the phenyl rings is evaluated using the Harmonic Oscillator Model of Aromaticity (HOMA) index. Intra- and inter-molecular non-covalent interactions are studied via Hirshfeld surface analysis, Independent Gradient Model (IGM), Quantum Theory of Atoms in Molecules (QTAIM), Non-Covalent Interaction (NCI) index, Electron Localisation Function (ELF), Core-Valence Bifurcation (CVB) index and Symmetry-Adapted Perturbation Theory (SAPT). Density Functional Theory (DFT) simulations were carried out in vacuo and with solvent reaction field based on Polarisable Continuum Model (IEF-PCM formulation) at the ωB97XD/6-311+G(2d,2p) level. Crystal structure analyses were performed for the data reported previously in the literature. The obtained results demonstrate that the three isomers differ greatly in their structural properties (molecular symmetry is broken for the ortho and meta isomers in the solid state) and ability to form intermolecular interactions, while retaining overall similar physico-chemical characteristics, e.g., aromaticity of the phenyl rings. It was found that the presence of the polar solvent does not significantly affect the structure of the studied compounds. An application of the Hirshfeld surface analysis revealed the nature of the non-covalent interactions present in the investigated crystals. The SAPT results showed that the stability of the dimers extracted from the crystals of the Schiff base derivatives arises from electrostatics and dispersion. Full article
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17 pages, 5773 KiB  
Communication
Binomial Distributed Data Confidence Interval Calculation: Formulas, Algorithms and Examples
by Lorentz Jäntschi
Symmetry 2022, 14(6), 1104; https://doi.org/10.3390/sym14061104 - 27 May 2022
Cited by 13 | Viewed by 1689
Abstract
When collecting experimental data, the observable may be dichotomous. Sampling (eventually with replacement) thus emulates a Bernoulli trial leading to a binomial proportion. Because the binomial distribution is discrete, the analytical evaluation of the exact confidence interval of the sampled outcome is a [...] Read more.
When collecting experimental data, the observable may be dichotomous. Sampling (eventually with replacement) thus emulates a Bernoulli trial leading to a binomial proportion. Because the binomial distribution is discrete, the analytical evaluation of the exact confidence interval of the sampled outcome is a mathematical challenge. This paper proposes three alternative confidence interval calculation methods that are characterized and exemplified. Full article
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19 pages, 1007 KiB  
Article
Microsolvation of Histidine—A Theoretical Study of Intermolecular Interactions Based on AIM and SAPT Approaches
by Beata Kizior, Jarosław J. Panek and Aneta Jezierska
Symmetry 2020, 12(7), 1153; https://doi.org/10.3390/sym12071153 - 10 Jul 2020
Cited by 3 | Viewed by 2920
Abstract
Histidine is unique among amino acids because of its rich tautomeric properties. It participates in essential enzymatic centers, such as catalytic triads. The main aim of the study is the modeling of the change of molecular properties between the gas phase and solution [...] Read more.
Histidine is unique among amino acids because of its rich tautomeric properties. It participates in essential enzymatic centers, such as catalytic triads. The main aim of the study is the modeling of the change of molecular properties between the gas phase and solution using microsolvation models. We investigate histidine in its three protonation states, microsolvated with 1:6 water molecules. These clusters are studied computationally, in the gas phase and with water as a solvent (Polarizable Continuum Model, PCM) within the Density Functional Theory (DFT) framework. The structural analysis reveals the presence of intra- and intermolecular hydrogen bonds. The Atoms-in-Molecules (AIM) theory is employed to determine the impact of solvation on the charge flow within the histidine, with emphasis on the similarity of the two imidazole nitrogen atoms—topologically not equivalent, they are revealed as electronically similar due to the heterocyclic ring aromaticity. Finally, the Symmetry-Adapted Perturbation Theory (SAPT) is used to examine the stability of the microsolvation clusters. While electrostatic and exchange terms dominate in magnitude over polarization and dispersion, the sum of electrostatic and exchange term is close to zero. This makes polarization the factor governing the actual interaction energy. The most important finding of this study is that even with microsolvation, the polarization induced by the presence of implicit solvent is still significant. Therefore, we recommend combined approaches, mixing explicit water molecules with implicit models. Full article
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