Anti-Cancer Efficacy of Silybin Derivatives - A Structure-Activity Relationship

0392676 - MBÚ 2014 RIV US eng J - Journal Article
Agarwal, Ch. - Wadhwa, R. - Deep, G. - Biedermann, David - Gažák, Radek - Křen, Vladimír - Agarwal, R.
Anti-Cancer Efficacy of Silybin Derivatives - A Structure-Activity Relationship.
PLoS ONE. Roč. 8, č. 3 (2013), e00074. ISSN 1932-6203. E-ISSN 1932-6203
R&D Projects: GA MŠMT(CZ) ME10027
Institutional support: RVO:61388971
Keywords : Silybin * silibinin * anti-cancer efficacy
Subject RIV: CE - Biochemistry
Impact factor: 3.534, year: 2013

Silybin or silibinin, a flavonolignan isolated from Milk thistle seeds, is one of the popular dietary supplements and has been extensively studied for its antioxidant, hepatoprotective and anti-cancer properties. We have envisioned that potency of silybin could be further enhanced through suitable modification/s in its chemical structure. Accordingly, here, we synthesized and characterized a series of silybin derivatives namely 2,3-dehydrosilybin (DHS), 7-O-methylsilybin (7OM), 7-Ogalloylsilybin (7OG), 7,23-disulphatesilybin (DSS), 7-O-palmitoylsilybin (7OP), and 23-O-palmitoylsilybin (23OP); and compared their anti-cancer efficacy using human bladder cancer HTB9, colon cancer HCT116 and prostate carcinoma PC3 cells. In all the 3 cell lines, DHS, 7OM and 7OG demonstrated better growth inhibitory effects and compared to silybin, while other silybin derivatives showed lesser or no efficacy. Next, we prepared the optical isomers (A and B) of silybin, DHS, 7OM and 7OG, and compared their anti-cancer efficacy. Isomers of these three silybin derivatives also showed better efficacy compared with respective silybin isomers, but in each, there was no clear cut silybin A versus B isomer activity preference
Permanent Link: http://hdl.handle.net/11104/0221497