Synthesis, photophysical properties, in vivo photosensitizing efficacy, and human serum albumin binding properties of some novel bacteriochlorins

Ravindra K. Pandey, Scott Constantine, Takaaki Tsuchida, Gang Zheng, Craig J. Medforth, Mohamed Aoudia, Andrei N. Kozyrev, Michael A J Rodgers, Harubumi Kato, Kevin M. Smith, Thomas J. Dougherty

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The synthesis, photophysical characteristics, in vive photosensitizing efficacy, human serum albumin (HSA) binding properties, and skin phototoxicity of some stable bacteriochlorins were investigated. The novel bacteriochlorins, obtained from chlorophyll-α, have long-wavelength absorptions in the range λmax = 734-758 nm. Preferential migration of ethyl over methyl substituents among ketobacteriochlorins obtained in the pinacol- pinacolone rearrangements of vic-dihydroxybacteriochlorins was confirmed by NOE studies. The bacteriochlorins show relatively low fluorescence quantum yields. Among all the bacteriochlorins the triplet states were quenched by ground state molecular oxygen in a relatively similar manner, yielding comparable singlet oxygen quantum yields. In preliminary in vive studies (DBA/2 mice, transplanted with SMT/F tumors), ketobacteriochlorins were found to be more photodynamically active than the related vic-dihydroxy analogues. Replacement of the methyl ester functionalities with di-tert-butylaspartic acids enhanced the in vive efficacy. Site specific human serum albumin (HSA) binding studies indicated a direct correlation between the ability of the compound to hind to the diazepam binding site (albumin site II) and the in vive photosensitizing efficacy.

Original languageEnglish
Pages (from-to)2770-2779
Number of pages10
JournalJournal of Medicinal Chemistry
Issue number17
Publication statusPublished - Aug 15 1997


ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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