title: Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal.
abstract: 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.
authors.affiliation: Department of Chemistry, Wake Forest University, Winston-Salem, NC, USA. jonespb@wfu.edu
authors.forename: Paul B
authors.initials: PB
authors.lastname: Jones
authors.forename: Robert G
authors.initials: RG
authors.lastname: Brinson
authors.forename: Saurav J
authors.initials: SJ
authors.lastname: Sarma
authors.forename: Salwa
authors.initials: S
authors.lastname: Elkazaz
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000880:Anthraquinones / Q000737:chemistry; D010084:Oxidation-Reduction; D010777:Photochemistry; D012995:Solubility; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000880:Anthraquinones; D014867:Water; C027576:4-hydroxy-2-nonenal