(22β,25R)-3β-Hydroxy-spirost-5-en-7-iminoxy-heptanoic acid exhibits anti-prostate cancer activity through caspase pathway

•Diverse long chain fatty acid/esters of diosgenin-7-ketoxime have been prepared.•Analogue 16, cytotoxicity IC50 = 12 μM prostate cancer, cell cycle arrest at S phase and induces apoptosis through caspase pathway.•Simultaneously antiinflammatory property by inhibition of TNF-α and IL-6.•Safe up to 1000 mg/kg dose in Swiss-albino mice.•Simultaneous, antiinflammatory property in an anticancer molecule is favourable.

Prostate cancer is one of the most common cancers in men. Diosgenin and related compounds are potential cytotoxic agents. Twelve diverse analogues of long chain fatty acid/ester of diosgenin-7-ketoxime have been prepared. Six of the analogues exhibited significant anticancer activity against a panel of human cancer cell lines with IC50 ranging from 12 to 35 μM. Compound 16, the best representative of the series exerted S phase arrest in DU145 prostate cancer cells and induced apoptosis through caspase pathway. Additionally, these analogues inhibited lipopolysaccharide induced pro-inflammatory cytokines (TNF-α and IL-6) up to 47.7% and 23.3% respectively. Compound 16 was found to be safe in acute oral toxicity in Swiss albino mice up to 300 mg/kg dose. The anticancer and antiinflammatory properties of compound 16 are important and can further be optimized for a better anti-prostate cancer candidate.

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