Hydroxyethylamide substituted triterpenoic acids hold good cytotoxicity for human tumor cells

Results in Chemistry

Hans-Peter Deigner¹  Toni C. Denner²  Sophie Hoenke²  Oliver Kraft²  René Csuk²  Ahmed Al-Harrasi³ 

[1] Furtwangen University, Institute of Precision Medicine, Medical and Life Science Faculty, Jakob–Kienzle–Str. 17, D-78054 Villigen–Schwenningen, Germany;Martin–Luther–University Halle–Wittenberg, Organic Chemistry, Kurt–Mothes–Str. 2, D–06120 Halle (Saale), Germany;University of Nizwa, Chair of Oman’s Medicinal Plants and Marine Natural Products, P.O. Box 33, PC 616, Birkat Al-Mauz, Nizwa, Sultanate of Oman;

关键词: Betulinic acid;    Oleanolic acid;    Ursolic acid;    Platanic acid;    Cytotoxicity;   

DOI  :  

来源: DOAJ

【 摘 要 】

Pentacyclic triterpenoic acids, betulinic acid, platanic acid, oleanolic acid and ursolic acid, were acetylated and subsequently converted into mono-, bis- and tris(hydroxyl)ethyl amides. While parent compounds are of none or minor cytotoxicity, these amides showed EC50 values even in low μM concentration for a variety of different human tumor cell lines. Especially a bis(hydroxyethyl)amide 12 derived from oleanolic acid held an EC50 = 7.7 μM for A375 melanoma cells while being less cytotoxic for non-malignant fibroblasts NIH 3 T3 (EC50 > 30 μM). Several of these amides were converted into their corresponding sulfamates. While these sulfamates held no inhibitory activity for the enzyme carbonic anhydrase II, the highest cytotoxicity was observed for a betulinic acid derived sulfamate 17 with an EC50 = 4.9 μM for A375 melanoma cells.

【 授权许可】

Unknown