TY - JOUR
T1 - Alkyl ether analogs of chlorophyll-a derivatives
T2 - Part 1. Synthesis, photophysical properties and photodynamic efficacy
AU - Pandey, Ravindra K.
AU - Sumlin, Adam B.
AU - Constantine, Scott
AU - Aoudia, Mohamed
AU - Potter, William R.
AU - Bellnier, David A.
AU - Henderson, Barbara W.
AU - Rodgers, Michael A.
AU - Smith, Kevin M.
AU - Dougherty, Thomas J.
PY - 1996
Y1 - 1996
N2 - 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).
AB - 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).
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U2 - 10.1111/j.1751-1097.1996.tb02442.x
DO - 10.1111/j.1751-1097.1996.tb02442.x
M3 - Article
C2 - 8787014
AN - SCOPUS:0030199072
SN - 0031-8655
VL - 64
SP - 194
EP - 204
JO - Photochemistry and Photobiology
JF - Photochemistry and Photobiology
IS - 1
ER -