Alkyl ether analogs of chlorophyll-a derivatives: Part 1. Synthesis, photophysical properties and photodynamic efficacy

Ravindra K. Pandey, Adam B. Sumlin, Scott Constantine, Mohamed Aoudia, William R. Potter, David A. Bellnier, Barbara W. Henderson, Michael A. Rodgers, Kevin M. Smith, Thomas J. Dougherty

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148 Citations (Scopus)

Abstract

The synthesis, preliminary in vivo biological activity, singlet oxygen and fluorescence yields of a series of alkyl ether derivatives of chlorophyll-a analogs are described. For short-chain carbon ethers (1-7 carbon units), it was observed that the biological activity increased by increasing the length of the carbon chain, being maximum in compounds with n- hexyl and n-heptyl chains. Related sensitizers prepared by reacting 2-(1- bromoethyl)-2-devinylpyropheophorbide-a with (sec)alcohols were found to be less effective. Under similar treatment conditions, photosensitizers containing cis- and trans- 3-hexenyl side chains were ineffective. Thus, both stereochemical and steric factors caused differences in sensitizing activity. In general, pyropheophorbide-a analogs were found to be more active than related chlorine, derivatives, in which the isocyclic ring (ring 'E') was cleaved. Related photosensitizers in the 9-deoxy- series were found to be as effective as the corresponding pyropheophorbide-a analogs. The photosensitizers prepared from pyropheophorhide-a methyl ester and chlorine6 trimethyl ester have lung wavelength absorption at 660 nm (ε 45000 to 50000). Reduction of the carbonyl group in the pyrophenphorbide-a to methylene (ring E) resulted in a blue shift to 648 nm (ε 38000).

Original languageEnglish
Pages (from-to)194-204
Number of pages11
JournalPhotochemistry and Photobiology
Volume64
Issue number1
Publication statusPublished - Jul 1996

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics

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    Pandey, R. K., Sumlin, A. B., Constantine, S., Aoudia, M., Potter, W. R., Bellnier, D. A., Henderson, B. W., Rodgers, M. A., Smith, K. M., & Dougherty, T. J. (1996). Alkyl ether analogs of chlorophyll-a derivatives: Part 1. Synthesis, photophysical properties and photodynamic efficacy. Photochemistry and Photobiology, 64(1), 194-204.