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Novel C3-Methylene-Bridged Indole Derivatives with and without Substituents at N1: The Influence of Substituents on Their Hemolytic, Cytoprotective, and Antimicrobial Activity

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cris.virtual.author-orcid0000-0002-8295-5980
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dc.abstract.enAlkaloids are natural compounds useful as scaffolds for discovering new bioactive molecules. This study utilized alkaloid gramine to synthesize two groups of C3-substituted indole derivatives, which were either functionalized at N1 or not. The compounds were characterized by spectroscopic methods. The protective effects of the new compounds against in vitro oxidative hemolysis induced by standard oxidant 2,2′-azobis(2-amidinopropane dihydro chloride (AAPH) on human erythrocytes as a cell model were investigated. Additionally, the compounds were screened for antimicrobial activity. The results indicated that most of the indole derivatives devoid of the N1 substitution exhibited strong cytoprotective properties. The docking studies supported the affinities of selected indole-based ligands as potential antioxidants. Furthermore, the derivatives obtained exhibited potent fungicidal properties. The structures of the eight derivatives possessing indole moiety bridged to the imidazole-, benzimidazole-, thiazole-, benzothiazole-, and 5-methylbenzothiazoline-2-thiones were determined by X-ray diffraction. The C=S bond lengths in the thioamide fragment pointed to the involvement of zwitterionic structures of varying contribution. The predominance of zwitterionic mesomers may explain the lack of cytoprotective properties, while steric effects, which limit multiple the hydrogen-bond acceptor properties of a thione sulfur, seem to be responsible for the high hemolytic activity.
dc.affiliationWydział Rolnictwa, Ogrodnictwa i Biotechnologii
dc.affiliation.instituteKatedra Gleboznawstwa i Mikrobiologii
dc.contributor.authorBabijczuk, Karolina
dc.contributor.authorBerdzik, Natalia
dc.contributor.authorNowak, Damian
dc.contributor.authorWarżajtis, Beata
dc.contributor.authorRychlewska, Urszula
dc.contributor.authorStarzyk, Justyna Irena
dc.contributor.authorMrówczyńska, Lucyna
dc.contributor.authorJasiewicz, Beata
dc.date.access2025-02-24
dc.date.accessioned2025-02-24T09:36:20Z
dc.date.available2025-02-24T09:36:20Z
dc.date.copyright2024-05-14
dc.date.issued2024
dc.description.abstract<jats:p>Alkaloids are natural compounds useful as scaffolds for discovering new bioactive molecules. This study utilized alkaloid gramine to synthesize two groups of C3-substituted indole derivatives, which were either functionalized at N1 or not. The compounds were characterized by spectroscopic methods. The protective effects of the new compounds against in vitro oxidative hemolysis induced by standard oxidant 2,2′-azobis(2-amidinopropane dihydro chloride (AAPH) on human erythrocytes as a cell model were investigated. Additionally, the compounds were screened for antimicrobial activity. The results indicated that most of the indole derivatives devoid of the N1 substitution exhibited strong cytoprotective properties. The docking studies supported the affinities of selected indole-based ligands as potential antioxidants. Furthermore, the derivatives obtained exhibited potent fungicidal properties. The structures of the eight derivatives possessing indole moiety bridged to the imidazole-, benzimidazole-, thiazole-, benzothiazole-, and 5-methylbenzothiazoline-2-thiones were determined by X-ray diffraction. The C=S bond lengths in the thioamide fragment pointed to the involvement of zwitterionic structures of varying contribution. The predominance of zwitterionic mesomers may explain the lack of cytoprotective properties, while steric effects, which limit multiple the hydrogen-bond acceptor properties of a thione sulfur, seem to be responsible for the high hemolytic activity.</jats:p>
dc.description.accesstimeat_publication
dc.description.bibliographyil., bibliogr.
dc.description.financepublication_nocost
dc.description.financecost0,00
dc.description.if4,9
dc.description.number10
dc.description.points140
dc.description.reviewreview
dc.description.versionfinal_published
dc.description.volume25
dc.identifier.doi10.3390/ijms25105364
dc.identifier.issn1422-0067
dc.identifier.urihttps://sciencerep.up.poznan.pl/handle/item/2502
dc.identifier.weblinkhttps://www.mdpi.com/1422-0067/25/10/5364
dc.languageen
dc.pbn.affiliationagriculture and horticulture
dc.relation.ispartofInternational Journal of Molecular Sciences
dc.relation.pagesart. 5364
dc.rightsCC-BY
dc.sciencecloudsend
dc.share.typeOPEN_JOURNAL
dc.subject.engramine
dc.subject.enindole derivatives
dc.subject.enthione derivatives
dc.subject.enanti-oxidant properties
dc.subject.enoxidative hemolysis
dc.subject.endocking study
dc.subject.encrystal structures
dc.titleNovel C3-Methylene-Bridged Indole Derivatives with and without Substituents at N1: The Influence of Substituents on Their Hemolytic, Cytoprotective, and Antimicrobial Activity
dc.title.volumeSpecial Issue Recent Studies on Biological Activities of Alkaloids and Their Modifications
dc.typeJournalArticle
dspace.entity.typePublication
oaire.citation.issue10
oaire.citation.volume25