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

*Corresponding author for this work

Research output: Contribution to journalArticle

150 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.