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

Trimethyl Lock: A Stable Chromogenic Substrate for Esterases

1, 2 and 1,* email
Received: 19 January 2008; Accepted: 30 January 2008 / Published: 31 January 2008
(This article belongs to the collection Prodrugs)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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
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MDPI and ACS Style

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

AMA Style

Levine MN, Lavis LD, Raines RT. Trimethyl Lock: A Stable Chromogenic Substrate for Esterases. Molecules. 2008; 13(2):204-211.

Chicago/Turabian Style

Levine, Michael N.; Lavis, Luke D.; Raines, Ronald T. 2008. "Trimethyl Lock: A Stable Chromogenic Substrate for Esterases." Molecules 13, no. 2: 204-211.

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