{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T21:06:56Z","timestamp":1792789616727,"version":"4.5.0"},"reference-count":87,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T00:00:00Z","timestamp":1715644800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"ID-UB","award":["054\/12\/SN\u015a.0011 (KB)"],"award-info":[{"award-number":["054\/12\/SN\u015a.0011 (KB)"]}]},{"name":"ID-UB","award":["054\/13\/SN\u015a\/0008 (NB)"],"award-info":[{"award-number":["054\/13\/SN\u015a\/0008 (NB)"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"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\u2032-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>","DOI":"10.3390\/ijms25105364","type":"journal-article","created":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T10:26:36Z","timestamp":1715682396000},"page":"5364","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Novel C3-Methylene-Bridged Indole Derivatives with and without Substituents at N1: The Influence of Substituents on Their Hemolytic, Cytoprotective, and Antimicrobial Activity"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5620-1800","authenticated-orcid":false,"given":"Karolina","family":"Babijczuk","sequence":"first","affiliation":[{"name":"Department of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Natalia","family":"Berdzik","sequence":"additional","affiliation":[{"name":"Department of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3739-3306","authenticated-orcid":false,"given":"Damian","family":"Nowak","sequence":"additional","affiliation":[{"name":"Department of Quantum Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3872-631X","authenticated-orcid":false,"given":"Beata","family":"War\u017cajtis","sequence":"additional","affiliation":[{"name":"Department of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Urszula","family":"Rychlewska","sequence":"additional","affiliation":[{"name":"Department of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Justyna","family":"Starzyk","sequence":"additional","affiliation":[{"name":"Department of Soil Science and Microbiology, Faculty of Agronomy, Horticulture, and Bioengineering, University of Life Science, Szyd\u0142owska 50, 60-656 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4425-5596","authenticated-orcid":false,"given":"Lucyna","family":"Mr\u00f3wczy\u0144ska","sequence":"additional","affiliation":[{"name":"Department of Cell Biology, Faculty of Biology, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 6, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6741-473X","authenticated-orcid":false,"given":"Beata","family":"Jasiewicz","sequence":"additional","affiliation":[{"name":"Department of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,14]]},"reference":[{"key":"ref_1","first-page":"439","article-title":"Tropane Alkaloids as Medicinally Useful Natural Products and Their Synthetic Derivatives as New Drugs","volume":"60","author":"Grynkiewicz","year":"2008","journal-title":"Pharmacol. 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