Syntheses and photosensitizing activity of porphyrins joined with ester linkages.
In order to investigate the structure of hematoporphyrin derivative and its purified version, Photofrin-II, porphyrin dimers with ester linkage were synthesized. 2,4-Diacetyldeuteroporphyrin dimethyl ester and protoporphyrin IX dimethyl ester were used as starting materials. The methyl esters were replaced by trimethylsilylethyl esters to protect the carboxylic groups. Deprotection using tetra-n-butylammonium fluoride in tetrahydrofuran regenerated the carboxylic functions. Reversed phase high performance liquid chromatography was used to compare the synthetic dimers with components of Photofrin-II. Our data indicate that these dimers are not components of Photofrin-II. During the synthesis of a 13C-labeled dimer with an ester linkage, a small amount of trimer was also isolated. The structures of these compounds were confirmed by nuclear magnetic resonance and mass spectroscopy. Using a standard screening system with DBA/2 mice bearing transplanted SMT-F tumors, these dimers were found not to be as active as Photofrin-II.
Pandey
R K
RK
Oncologic Foundation of Buffalo, New York 14203.
Dougherty
T J
TJ
D000818:Animals; D017323:Dihematoporphyrin Ether; D017324:Hematoporphyrin Derivative; D006414:Hematoporphyrin Photoradiation; D006415:Hematoporphyrins / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008811:Mice, Inbred DBA; D009374:Neoplasms, Experimental / Q000188:drug therapy; D010778:Photochemotherapy
D006415:Hematoporphyrins; D017324:Hematoporphyrin Derivative; D017323:Dihematoporphyrin Ether