Počet záznamů: 1

Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters

  1. 1.
    0369330 - MBU-M 2012 RIV US eng J - Článek v odborném periodiku
    Gažák, Radek - Valentová, K. - Fuksová, Kateřina - Marhol, Petr - Kuzma, Marek - Medina, M. A. - Oborná, I. - Ulrichová, J. - Křen, Vladimír
    Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters.
    Journal of Medicinal Chemistry. Roč. 54, č. 20 (2011), s. 7397-7407 ISSN 0022-2623
    Grant CEP: GA ČR GAP207/10/0288; GA ČR(CZ) GAP301/11/0767; GA MŠk OC08049
    Výzkumný záměr: CEZ:AV0Z50200510
    Klíčová slova: Silybin * gallates * HUVEC
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 5.248, rok: 2011

    The synthesis of various silybin monogalloyl esters was developed, and their antiangiogenic activities were evaluated in a variety of in vitro tests with human umbilical vein endothelial cells (HUVECs). A structure-activity relationship (SAR) study found the regioselectivity of the silybin galloylation to be highly significant. Silybin (as an equimolar mixture of two diastereomers A and B) exhibited quite poor antiangiogenic activities, whereas its B isomer is more active than silybin A. Galloylation of phenolic OH groups of natural silybin (a mixture of both isomers) leads to increases in their antiangiogenic activities, which is more apparent with the 7-OH than the 20-OH. In contrast, gallates at aliphatic OH groups either had a comparable activity to the parent compound or are even worse than silybin, which was observed in the case of 3-O-galloylsilybin. The most effective 7-O-galloylsilybin has also been prepared from pure silybins A and B. B isomer was more active than A isomer
    Trvalý link: http://hdl.handle.net/11104/0203423