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Design and Synthesis of Fluoroacylshikonin as an Anticancer Agent
Author(s) -
Kong WenYao,
Chen XiaoFeng,
Shi Jing,
Baloch Shahla Karim,
Qi JinLiang,
Zhu HaiLiang,
Wang XiaoMing,
Yang YongHua
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22209
Subject(s) - chemistry , docking (animal) , stereochemistry , chirality (physics) , lead compound , melanoma , combinatorial chemistry , biochemistry , cancer research , in vitro , medicine , chiral symmetry breaking , physics , nursing , quantum mechanics , nambu–jona lasinio model , quark , biology
A series of shikonin derivatives, selectively acylated by various fluorinated carboxylic acids at the side chain of shikonin, were synthesized and their anticancer activity evaluated, in which eight compounds are reported for the first time. Among all the compounds tested, compound S7 showed the most potent anticancer activity against B16‐F10 (malignant melanoma cells), MG63 (human osteosarcoma cells), and A549 (lung cancer cells) with IC 50 0.39 ± 0.01, 0.72 ± 0.04 and 0.58 ± 0.02 µmol/L. Docking simulation of compound S7 was carried out to position S7 into a tubulin active site to determine the probable binding conformation. All the results suggested that compound S7 may be a potential anticancer agent. Chirality 25:757–762, 2013 . © 2013 Wiley Periodicals, Inc.