Stictamides A-C, MMP12 Inhibitors Containing 4-Amino-3-hydroxy-5-phenylpentanoic Acid Subunits

被引：15

作者：

Liang, Zhibin ^{[1
]}

Sorribas, Analia ^{[1
]}

Sulzmaier, Florian J. ^{[4
]}

Jimenez, Jorge I. ^{[5
]}

Wang, Xin ^{[2
]}

Sauvage, Thomas ^{[3
]}

Yoshida, Wesley Y. ^{[1
]}

Wang, Guangyi ^{[2
]}

Ramos, Joe W. ^{[4
]}

Williams, Philip G. ^{[1
,4
]}

机构：

[1] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA

[2] Univ Hawaii Manoa, Dept Oceanog, Honolulu, HI 96822 USA

[3] Univ Hawaii Manoa, Dept Bot, Honolulu, HI 96822 USA

[4] Univ Hawaii, Ctr Canc, Honolulu, HI 96813 USA

[5] AgraQuest Inc, Davis, CA 95618 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 10期

基金：

美国国家科学基金会;

关键词：

MATRIX-METALLOPROTEINASE INHIBITORS; AMINO-ACIDS; EXPRESSION; PEPSTATIN; INVASION; DEPSIPEPTIDES; OPTIMIZATION; MACROPHAGES; PROGRESSION; PROTEASES;

D O I：

10.1021/jo200241h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 mu M and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism.

引用

页码：3635 / 3643

页数：9

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