title: Synthesis and photosensitizing efficacy of isomerically pure bacteriopurpurinimides.
abstract: 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.
authors.affiliation: PDT Center, Department of Dermatology, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
authors.forename: Yihui
authors.initials: Y
authors.lastname: Chen
authors.forename: Adam
authors.initials: A
authors.lastname: Sumlin
authors.forename: Janet
authors.initials: J
authors.lastname: Morgan
authors.forename: Amy
authors.initials: A
authors.lastname: Gryshuk
authors.forename: Allan
authors.initials: A
authors.lastname: Oseroff
authors.forename: Barbara W
authors.initials: BW
authors.lastname: Henderson
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Dougherty
authors.forename: Ravindra K
authors.initials: RK
authors.lastname: Pandey
mesh_terms: 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
chemical_list: D017319:Photosensitizing Agents