Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00581608" target="_blank" >RIV/61388963:_____/24:00581608 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/24:43929074 RIV/60461373:22330/24:43929074 RIV/00216208:11310/24:10476385
Result on the web
<a href="https://doi.org/10.1039/D3MD00535F" target="_blank" >https://doi.org/10.1039/D3MD00535F</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d3md00535f" target="_blank" >10.1039/d3md00535f</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
RSC Medicinal Chemistry
ISSN
2632-8682
e-ISSN
2632-8682
Volume of the periodical
15
Issue of the periodical within the volume
1
Country of publishing house
GB - UNITED KINGDOM
Number of pages
22
Pages from-to
322-343
UT code for WoS article
001127188400001
EID of the result in the Scopus database
2-s2.0-85180612986