title: Does one keto group matter? Structure-activity relationships of glycyrrhetinic acid derivatives modified at position C-11.
abstract: Several triterpenoic acids display a remarkable cytotoxicity on tumor cells. Glycyrrhetinic acid - the main content of the licorice root - possesses an apoptotic effect on tumor cells. Previous studies pointed out the presence of a keto group at position C-11 in glycyrrhetinic acid derivatives as the main reason for its apoptotic activity. Several pairs of derivatives were synthesized differing only at position C-11. These compounds were tested in a sulforhodamine B colorimetric assay for cytotoxicity screening on 12 tumor cell lines and mouse embryonic fibroblasts (NIH3T3). Our results show that there is no direct relation between the existence of the C-11 keto group and the apoptotic activity of the compounds.
authors.affiliation: Martin-Luther-Universität Halle-Wittenberg, Bereich Organische Chemie, Halle (Saale), Germany. rene.csuk@chemie.uni-halle.de
authors.forename: René
authors.initials: R
authors.lastname: Csuk
authors.forename: Stefan
authors.initials: S
authors.lastname: Schwarz
authors.forename: Ralph
authors.initials: R
authors.lastname: Kluge
authors.forename: Dieter
authors.initials: D
authors.lastname: Ströhl
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D005347:Fibroblasts / Q000187:drug effects / Q000473:pathology; D006034:Glycyrrhetinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D006034:Glycyrrhetinic Acid