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Synthesis and photosensitizing efficacy of isomerically pure bacteriopurpurinimides
Yihui Chen1, Adam Sumlin, Janet Morgan
1PDT Center, Department of Dermatology, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
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.
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