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https://open.uns.ac.rs/handle/123456789/18866
Назив: | Evaluation of A-ring fused pyridine d-modified androstane derivatives for antiproliferative and aldo-keto reductase 1C3 inhibitory activity | Аутори: | Savić (Zaviš) Marina Ajduković Jovana J. Plavša Jovana J. Bekić Sofija Ćelić Andjelka S. Klisurić Olivera R. Jakimov Dimitar Petri Edward T. Djurendić Evgenija A. |
Датум издавања: | 2018 | Часопис: | MedChemComm | Сажетак: | © 2018 The Royal Society of Chemistry. New A-ring pyridine fused androstanes in 17a-homo-17-oxa (d-homo lactone), 17α-picolyl or 17(E)-picolinylidene series were synthesized and validated by X-ray crystallography, HRMS, IR and NMR spectroscopy. Novel compounds 3, 5, 8 and 12 were prepared by treatment of 4-en-3-one or 4-ene-3,6-dione d-modified androstane derivatives with propargylamine catalyzed by Cu(ii), and evaluated for potential anticancer activity in vitro using human cancer cell lines and recombinant targets of steroidal anti-cancer drugs. Pyridine fusion to position 3,4 of the A-ring may dramatically enhance affinity of 17α-picolyl compounds for CYP17 while conferring selective antiproliferative activity against PC-3 cells. Similarly, pyridine fusion to the A-ring of steroidal d-homo lactones led to identification of new inhibitors of aldo-keto reductase 1C3, an enzyme targeted in acute myeloid leukemia, breast and prostate cancers. One A-pyridine d-lactone steroid 5 also has selective submicromolar antiproliferative activity against HT-29 colon cancer cells. None of the new derivatives have affinity for estrogen or androgen receptors in a yeast screen, suggesting negligible estrogenicity and androgenicity. Combined, our results suggest that A-ring pyridine fusions have potential in modulating the anticancer activity of steroidal compounds. | URI: | https://open.uns.ac.rs/handle/123456789/18866 | ISSN: | 2040-2503 | DOI: | 10.1039/c8md00077h |
Налази се у колекцијама: | PMF Publikacije/Publications |
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