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利用点击化学探索硫杂环丙烷作为明胶酶抑制剂的功能空间。

Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry.

作者信息

Testero Sebastian A, Llarrull Leticia I, Fisher Jed F, Chang Mayland, Mobashery Shahriar

机构信息

Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.

出版信息

ARKIVOC. 2011;2011(7):221-226. doi: 10.3998/ark.5550190.0012.719. Epub 2011 Feb 27.

DOI:10.3998/ark.5550190.0012.719
PMID:32774191
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7412954/
Abstract

A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative , showed very good activity (>50% inhibitory activity following a 3 h pre-incubation of at a concentration of 3 μM) as an inhibitor of human matrix metalloproteinase-2.

摘要

对一系列苯氧基苯基取代的硫杂环丙烷SB - 3CT的4 - [(三唑基)甲氧基]苯基类似物进行了评估，以确定其抑制明胶酶（基质金属蛋白酶家族的酶成员）的能力。这些抑制剂的三唑部分是通过Meldal - Sharpless铜催化的叠氮化物和末端炔烃的Huisgen偶极环加成反应组装而成。虽然这些三唑衍生物作为明胶酶抑制剂具有一定活性，但偶极环加成反应中使用的中间体4 - (炔丙氧基)苯基衍生物作为人基质金属蛋白酶 - 2的抑制剂表现出非常好的活性（在3 μM浓度下预孵育3小时后抑制活性>50%）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/907c2874b1ac/nihms-1059152-f0029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/4bcffba2a3b8/nihms-1059152-f0022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/3ec6721d88e4/nihms-1059152-f0023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/6b3f28c32c51/nihms-1059152-f0024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/53b2cdb72cd0/nihms-1059152-f0025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/0d9ad8404bd0/nihms-1059152-f0026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/aa080615801d/nihms-1059152-f0027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/508926830769/nihms-1059152-f0028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/907c2874b1ac/nihms-1059152-f0029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/4bcffba2a3b8/nihms-1059152-f0022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/3ec6721d88e4/nihms-1059152-f0023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/6b3f28c32c51/nihms-1059152-f0024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/53b2cdb72cd0/nihms-1059152-f0025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/0d9ad8404bd0/nihms-1059152-f0026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/aa080615801d/nihms-1059152-f0027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/508926830769/nihms-1059152-f0028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cbc/7412954/907c2874b1ac/nihms-1059152-f0029.jpg

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本文引用的文献

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In situ click chemistry: probing the binding landscapes of biological molecules.原位点击化学：探测生物分子的结合景观。
Chem Soc Rev. 2010 Apr;39(4):1252-61. doi: 10.1039/b901969n. Epub 2010 Mar 1.
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Active site ring-opening of a thiirane moiety and picomolar inhibition of gelatinases.硫杂环戊烷部分的活性部位开环和明胶酶的皮摩尔抑制作用。
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Matrix metalloproteinases: what do they not do? New substrates and biological roles identified by murine models and proteomics.基质金属蛋白酶：它们无所不能？通过小鼠模型和蛋白质组学鉴定的新底物及生物学作用
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