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Molecules 2008, 13(2), 204-211; doi:10.3390/molecules13020204

Trimethyl Lock: A Stable Chromogenic Substrate for Esterases

1, 2 and 1,*
1 Department of Biochemistry, University of Wisconsin–Madison, 433 Babcock Drive, Madison, WI 53706-1544, USA 2 Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706-1322, USA
* Author to whom correspondence should be addressed.
Received: 19 January 2008 / Accepted: 30 January 2008 / Published: 31 January 2008
(This article belongs to the Special Issue Prodrugs)
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p-Nitrophenyl acetate is the most commonly used substrate for detecting thecatalytic activity of esterases, including those that activate prodrugs in human cells. Thissubstrate is unstable in aqueous solution, limiting its utility. Here, a stable chromogenicsubstrate for esterases is produced by the structural isolation of an acetyl ester andp-nitroaniline group using a trimethyl lock moiety. Upon ester hydrolysis, unfavorablesteric interactions between the three methyl groups of this o-hydroxycinnamic acidderivative encourage rapid lactonization to form a hydrocoumarin and releasep-nitroaniline. This “prochromophore” could find use in a variety of assays.
Keywords: enzyme catalysis; chromogenic substrate; p-nitrophenyl acetate; trimethyl lock enzyme catalysis; chromogenic substrate; p-nitrophenyl acetate; trimethyl lock
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Levine, M.N.; Lavis, L.D.; Raines, R.T. Trimethyl Lock: A Stable Chromogenic Substrate for Esterases. Molecules 2008, 13, 204-211.

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