Synthesis and photosensitizing efficacy of isomerically pure bacteriopurpurinimides.
The isomerically pure 3-deacetyl-3-(1-heptyloxy)ethylbacteriopurpurin-N-hexylimides exhibiting long-wavelength absorption near 800 nm were obtained from 3-acetylbacteriopurpurin-N-hexylimide in high stereospecificity by following Corey's synthetic approach. Both heptyl ether derivatives (R- and S-isomers) showed similar in vitro photosensitizing efficacy and limited skin phototoxicity and were found to localize in mitochondria. However, in preliminary in vivo screening, compared to the S-isomer, the corresponding R-isomer produced enhanced in vivo photodynamic therapy efficacy.
Chen
Yihui
Y
PDT Center, Department of Dermatology, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
Sumlin
Adam
A
Morgan
Janet
J
Gryshuk
Amy
A
Oseroff
Allan
A
Henderson
Barbara W
BW
Dougherty
Thomas J
TJ
Pandey
Ravindra K
RK
D000818:Animals; D001671:Biochemistry / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D051379:Mice; D008809:Mice, Inbred C3H; D009374:Neoplasms, Experimental / Q000188:drug therapy; D010778:Photochemotherapy / Q000379:methods; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D017319:Photosensitizing Agents