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  • Title: Synthesis and biological evaluation of 4β-acrylamidopodophyllotoxin congeners as DNA damaging agents.
    Author: Kamal A, Suresh P, Janaki Ramaiah M, Mallareddy A, Kumar BA, Raju P, Vinay Gopal J, Pushpavalli SN, Lavanya A, Sarma P, Pal-Bhadra M.
    Journal: Bioorg Med Chem; 2011 Aug 01; 19(15):4589-600. PubMed ID: 21737288.
    Abstract:
    A series of new 4β-acrylamidopodophyllotoxin derivatives (13a-o) were synthesized by coupling of substituted acrylic acids (10a-l and 11m-o) to the 4β-aminopodophyllotoxin. The synthesized derivatives 13a-o were evaluated for their cytotoxicity against five human cancer cell lines (breast, oral, colon, lung and ovarian). These podophyllotoxin conjugates have shown promising activity with GI₅₀ values ranging from <0.1 to 0.29 μM. Some of the compounds 13j, 13k and 13l that showed significant antiproliferative activity were also evaluated for related cytotoxic effects in MCF-7 cells, and compared to etoposide. These compounds (13j, 13k and 13l) showed G2/M cell cycle arrest and the apoptotic event was found to be due to both the single-strand DNA breaks as observed by comet assay as well as double-strand breaks as observed by the large accumulation of gamma H2AX foci.
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