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Synthesis and cytotoxic properties of alkynic triterpenoid Mannich compounds

Ronny Sczepek, Christoph Nitsche, Lucie Heller, Bianka Siewert, Renate Schäfer, Franziska Flemming, Choijiljav Otgonbayar, René Csuk


In summary, we prepared alkynic Mannich bases of betulinic or glycyrrhetinic acid; many of these compounds showed an improved cytotoxicity as compared to their parent compounds glycyrrhetinic or betulinic acid. The selectivity between malignant and nonmalignant cells is not affected by these transformations. The highest cytotoxicity was determined for a Mannich compound derived from glycyrrhetinic acid, and EC50 values as low as 3.3 myM were achieved for this compound employing the human submandibular carcinoma cell line A253. As shown by AO/PI staining as well as by DNA-laddering experiments this compound acts by apoptosis.

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