Diego Mauricio Gil

M. Judith Percino

Subbiah Thamotharan

Frontiers in Chemistry

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Editorial: Experimental andtheoretical investigation ofnon-covalent interactions inpotential bioactive compoundsSubbiah Thamotharan1*, M. Judith Percino2 andDiego Mauricio Gil31Biomolecular Crystallography Laboratory and DBT-Bioinformatics Center, School of Chemical andBiotechnology, SASTRA Deemed University, Thanjavur, India, 2Unidad de Polímeros y ElectrónicaOrgánica, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Puebla, México, 3INBIOFAL(CONICET-UNT), Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia,Universidad Nacional de Tucumán, San Miguel de Tucumán, ArgentinaKEYWORDSweak noncovalent interaction, energetics, bioactive, DFT, CLP-PIXEL energy, hirshfeldsurfaceEditorial on the Research TopicExperimental and theoretical investigation of non-covalent interactions inpotential bioactive compoundsIntroductionThe properties of the bioactive solids are primarily dependent on the various types ofnoncovalent interactions such as hydrogen, halogen, chalcogen, pnictogen, tetrel, triel, π-stacking, cation-π and anion-π, and lone pair-π interactions (Jena et al., 2022; Schneider,2022). Among various non-covalent interactions, hydrogen bonds and π-stackinginteractions are well recognized in structural chemistry, biology, and crystal engineering.The other mentioned interactions play an essential role in synthesis, catalysis, drug designand materials science, crystal engineering, etc. either alone or in combination with multipletypes of noncovalent interactions. Therefore, understanding the presence, hierarchy ofinteractions, energetics, and importance of different interactions is vital to understanding thebiological action of compounds and designing more specific and active molecules. Severalmodern theoretical tools such as the Hirshfeld surface, CLP-PIXEL energy, quantum theoryof atoms in molecules (QTAIM), and molecular docking aid in understanding the role ofvarious intermolecular interactions in the context of supramolecular assemblies andbiological action of crystalline solids.In this Research Topic, we collected four research articles which highlight theimportance of various weak noncovalent interactions in different systems. Saeed et al.described the crystal structure analysis of N-((4-acetylphenyl) carbamothioyl) pivalamide,and the molecular conformation of this molecule is locked by an intramolecular N–H···Ohydrogen bond that generatesa S (6) ring Saeed et al. The intermolecular N–H···O=C andC–H···π in addition to π-stacking interactions are formed in the solid state to stabilize theOPEN ACCESSEDITED AND REVIEWED BYTony D. James,University of Bath, United Kingdom*CORRESPONDENCESubbiah Thamotharan,thamu@scbt.sastra.eduRECEIVED 24 October 2023ACCEPTED 03 November 2023PUBLISHED 13 November 2023CITATIONThamotharan S, Percino MJ and Gil DM(2023), Editorial: Experimental andtheoretical investigation of non-covalentinteractions in potentialbioactive compounds.Front. Chem. 11:1326955.doi: 10.3389/fchem.2023.1326955COPYRIGHT© 2023 Thamotharan, Percino and Gil.This is an open-access article distributedunder the terms of the CreativeCommons Attribution License (CC BY).The use, distribution or reproduction inother forums is permitted, provided theoriginal author(s) and the copyrightowner(s) are credited and that the originalpublication in this journal is cited, inaccordance with accepted academicpractice. No use, distribution orreproduction is permitted which does notcomply with these terms.Frontiers in Chemistry frontiersin.org01TYPE EditorialPUBLISHED 13 November 2023DOI 10.3389/fchem.2023.1326955crystal structure. The molecular docking analysis of this compoundagainst four biological targets, namely, α-amylase, urease,acetylcholinesterase (AChE), and butylcholinesterase (BChE),suggests that AChE and BChE have a relatively stronger bindingto the compound than the other two protein targets. These findingsare in good agreement with those from the in vitro experiment.Gunasekaran et al. identified potential bioactive phytochemicalsfrom leaf extracts of Aegle marmelos. In particular, threephytochemicals, aegeline, marmin, and marminol, showedinhibition of sperm hyaluronidase activity, as evident from thein vitro assay Gunasekaran et al.. Further, in silico moleculardocking analysis reveals the key active site residues are involvedin the molecular recognition of aegeline, marmin and marmenolphytochemicals. These phytochemicals establish hydrogen bondsand hydrophobic interactions at the active site residues. Thetopological properties of the intermolecular interactions formedbetween the ligands and active site residues provided the strengthof these interactions. Further, the noncovalent interaction (NCI)plot reveals the nature of interactions between ligand and enzymes.Percino et al. synthesized two positional isomers of acrylonitrilederivatives, and X-ray diffraction analysis revealed that they exhibitsimilar crystal packing and hence similar optical properties Percinoet al.. Hirshfeld surface analysis reveals the effect of positional isomerson the intermolecular interactions formed in the crystal structures. Thecharacteristic intramolecular C–H···C(π) interaction is observed inthese structure and helps to maintain the molecular conformation.Weak C–H···π and C–H···N interactions dominate the crystal packing.The energetics of molecular dimers held by various interactions andeach of these interactions was further characterized by the QTAIMapproach. This study clearly demonstrated the isomeric effect usingX-ray structures, and various theoretical calculations help to designnovel molecules with desired properties. Aguiar et al. demonstrated theeffect of water molecules on paraquat salts. DFT calculations werecarried out to obtain the chemical reactivity of the bipyridylium cation,and supramolecular arrangements were analyzed Aguiar et al.. Thesupramolecular assemblies are generated via various shortintermolecular contacts such as O–H···O and C–H···O/Cl hydrogenbonds. It is interesting to note that the energy associated with C–H···Clis remarkably different in hydrated and anhydrous systems of paraquatsalts.In conclusion, the study of various weak molecular interactionsin different molecular solids and bioactive compounds with theirbiological targets has gained great attention in recent years to help usunderstand the molecular behaviors in a solid state and in thebiological system. This Research Topic clearly captures theimportance of studying noncovalent interactions to betterunderstand the system to design novel molecules with desiredproperties to some extent.Author contributionsST: Conceptualization, Writing–original draft, Writing–reviewand editing. MP: Writing–review and editing. DG: Writing–reviewand editing.FundingThe author(s) declare that no financial support was received forthe research, authorship, and/or publication of this article.AcknowledgmentsWe gratefully thank all the authors and reviewers who haveparticipated in this Research Topic. The authors thank theLaboratorio Nacional de Supercómputo del Sureste (LNS-BUAP)and SASTRA Deemed University for computational resources.Conflict of interestThe authors declare that the research was conducted in theabsence of any commercial or financial relationships that could beconstrued as a potential conflict of interest.Publisher’s noteAll claims expressed in this article are solely those of the authorsand do not necessarily represent those of their affiliatedorganizations, or those of the publisher, the editors and thereviewers. Any product that may be evaluated in this article, orclaim that may be made by its manufacturer, is not guaranteed orendorsed by the publisher.ReferencesJena, S., Dutta, J., Tulsiyan, K. D., Sahu, A. K., Choudhury, S. S., and Biswal, H. S.(2022). Noncovalent interactions in proteins and nucleic acids: beyond hydrogenbonding and π-stacking. Chem. Soc. Rev. 51, 4261–4286. doi:10.1039/D2CS00133KSchneider, H.-J. (2022). Noncovalent interactions: a brief account of a long history.J. Phys. Org. Chem. 35, e4340. doi:10.1002/poc.4340Frontiers in Chemistry frontiersin.org02Thamotharan et al. 10.3389/fchem.2023.1326955

Editorial: Experimental and theoretical investigation of non-covalent interactions in potential bioactive compounds

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Editorial: Experimental and theoretical investigation of non-covalent interactions in potential bioactive compounds

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