Solid-phase synthesis of a combinatorial methylated (±)- epigallocatechin gallate library and the growth-inhibitory effects of these compounds on melanoma B16 cells

Hiroshi Tanaka, Maasa Yamanouchi, Haruko Miyoshi, Keisuke Hirotsu, Hirofumi Tachibana, Takashi Takahashi

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15 Citations (Scopus)

Abstract

We report on the solid-phase synthesis of a combinatorial methylated (±)-epigallocatechin gallate (EGCG) library and its biological evaluation. Epigallocatechin gallate (EGCG) and its methylated derivatives, which are members of the catechin family, exhibit various anti-cancer effects. The solid-phase synthesis of methylated EGCG involves the preparation of the αl-acyloxyketone by the coupling of a solid-supported aldehyde with a ketone and an acid. The subsequent release and reductive etherification reaction of the solid-supported α-acyloxyketone provide the protected EGCG in good total yields. Sixty-four methylated EGCGs were successfully prepared. The growth-inhibitory effects of the methylated EGCG library were also examined. Although methylation of EGCG generally causes reduced growth inhibition, the growth-inhibitory effect of 7-OMe EGCGs was comparable to that of EGCG. The 7-OMe EGCGs are attractive drug candidates because of their enhanced bioavailability.

Original languageEnglish
Pages (from-to)2231-2248
Number of pages18
JournalChemistry - An Asian Journal
Volume5
Issue number10
DOIs
Publication statusPublished - Oct 4 2010

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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