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

Department of Chemistry, Wake Forest University, Winston-Salem, NC, USA. jonespb@wfu.edu

Organic & biomolecular chemistry 2008 Nov 21

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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.

Citation

Paul B Jones, Robert G Brinson, Saurav J Sarma, Salwa Elkazaz. Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal. Organic & biomolecular chemistry. 2008 Nov 21;6(22):4204-11