Mimicking the biological activity of diazobenzo[b]fluorene natural products with electronically tuned diazofluorene analogs.
Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells.
Zeng
Wei
W
Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA.
Eric Ballard
T
T
Tkachenko
Alexander G
AG
Burns
Virginia A
VA
Feldheim
Daniel L
DL
Melander
Christian
C
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002227:Carbazoles / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D004249:DNA Damage / Q000187:drug effects*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D018716:Molecular Mimicry; D013329:Structure-Activity Relationship; D000095602:Angucyclines and Angucyclinones
D000970:Antineoplastic Agents; D002227:Carbazoles; D005449:Fluorenes; C088442:kinamycin D; D000095602:Angucyclines and Angucyclinones