Diels-Alder adducts of vinyl porphyrins: synthesis and in vivo photodynamic effect against a rat bladder tumor.
Benzoporphyrin derivatives have been proposed as potential photosensitizers for photodynamic therapy. We have prepared a number of benzoporphyrin derivatives and tested their effect, in combination with red light, on the N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide (FANFT) induced rat bladder tumor (AY-27) transplanted into Fischer CDF(F344)/CrlBr rats. Tetracyanoethylene (TCNE) adducts showed very little activity, which may be attributable to their poor tumor uptake or to chemical instability of the adduct under physiological conditions. However, dimethyl acetylenedicarboxylate (DMAD) adducts tested showed greater cytotoxic effect than hematoporphyrin derivative and similar activities to metallopurpurins when tested under the same protocol.
Morgan
A R
AR
Department of Chemistry, University of Toledo, Ohio 43606.
Garbo
G M
GM
Keck
R W
RW
Miller
R A
RA
Selman
S H
SH
Skalkos
D
D
D000114:Acetylene / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D000480:Alkynes; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D010778:Photochemotherapy; D011166:Porphyrins / Q000138:chemical synthesis* / Q000627:therapeutic use; D051381:Rats; D013329:Structure-Activity Relationship; D001749:Urinary Bladder Neoplasms / Q000188:drug therapy*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use
D000480:Alkynes; D011166:Porphyrins; D014753:Vinyl Compounds; C022918:acetylenedicarboxylic acid dimethyl ester; D000114:Acetylene