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Syntheses and Photosensitizing Activity of Porphyrins Joined with Ester Linkages

Oncologic Foundation of Buffalo, Buffalo, New York 14203 [R. K. P.], and Radiation Biology, Department of Radiation Medicine, Roswell Park Memorial Institute, Buffalo, New York 14263 [T. J. D.]

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.

¹ To whom requests for reprints should be addressed, at Oncologic Foundation of Buffalo, 225 Oak Street, Suite 200, Buffalo, NY 14203.

Received 6/16/88. Revised 10/28/88. Revised 1/ 5/89. Accepted 1/10/89.