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Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety
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SYSNO ASEP 0581608 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety Author(s) Formánek, B. (CZ)
Dupommier, D. (CZ)
Volfová, T. (CZ)
Rimpelová, S. (CZ)
Škarková, A. (CZ)
Herciková, J. (CZ)
Rösel, D. (CZ)
Brábek, J. (CZ)
Perlíková, Pavla (UOCHB-X) RID, ORCIDSource Title RSC MEDICINAL CHEMISTRY. - : Royal Society of Chemistry
Roč. 15, č. 1 (2024), s. 322-343Number of pages 22 s. Language eng - English Country GB - United Kingdom Keywords actin polymerization ; cellular structures ; alkyl-halides R&D Projects LX22NPO5102 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 001127188400001 EID SCOPUS 85180612986 DOI 10.1039/d3md00535f Annotation Cytochalasans are known as inhibitors of actin polymerization and for their cytotoxic and migrastatic activity. In this study, we synthesized a series of cytochalasin derivatives that lack a macrocyclic moiety, a structural element traditionally considered essential for their biological activity. We focused on substituting the macrocycle with simple aryl-containing sidechains, and we have also synthesized compounds with different substitution patterns on the cytochalasin core. The cytochalasin analogues were screened for their migrastatic and cytotoxic activity. Compound 24 which shares the substitution pattern with natural cytochalasins B and D exhibited not only significant in vitro migrastatic activity towards BLM cells but also demonstrated inhibition of actin polymerization, with no cytotoxic effect observed at 50 mu M concentration. Our results demonstrate that even compounds lacking the macrocyclic moiety can exhibit biological activities, albeit less pronounced than those of natural cytochalasins. However, our findings emphasize the pivotal role of substituting the core structure in switching between migrastatic activity and cytotoxicity. These findings hold significant promise for further development of easily accessible cytochalasan analogues as novel migrastatic agents. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2025 Electronic address https://doi.org/10.1039/D3MD00535F
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