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