Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal

Paul B. Jones; Robert G. Brinson; Saurav J. Sarma; Salwa Elkazaz

doi:10.1039/B810954K

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Organic & Biomolecular Chemistry

Issue 22, 2008

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Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal

Paul B. Jones , Robert G. Brinson , Saurav J. Sarma and Salwa Elkazaz

Org. Biomol. Chem., 2008, 6, 4204-4211

DOI: 10.1039/B810954K
Received 27 Jun 2008, Accepted 05 Aug 2008
First published on the web 19 Sep 2008

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During the course of our study on the photochemistry of 1-alkoxy-9,10-anthraquinones, we have developed a second generation of a caged 4-hydroxy-trans-2-nonenal (4-HNE). As we optimized the anthraquinonyl chromophore to achieve water solubility, we studied the photochemistry of various substituents to understand their effect on the photochemistry. We observed a significant heavy atom effect that severely reduced the rate of oxidative cleavage of the alkoxy group. Based on the results of our substituent study, we designed a new caged 4-HNE that is soluble under physiological conditions, and that releases 4-HNE photochemically in high yield.

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Organic & Biomolecular Chemistry

Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal

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