Synthesis and in vivo photodynamic activity of some bacteriochlorin derivatives against bladder tumors in rodents.
Bacteriochlorins have been suggested as potential photosensitizers for use in photodynamic therapy. We have shown that bacteriochlorin-like macrocycles can be generated through cyclization of either 5,10- or 5,15-bis[(ethoxycarbonyl)vinyl]porphyrins; however, the resulting products are rapidly decomposed on exposure to air. More stable systems can be generated by Diels-Alder reactions between dienophiles such as dimethyl acetylenedicarboxylate or tetracyanoethylene, and vinylporphyrinones. Although spectroscopic properties of these latter products resemble those of porphyrinones rather than bacteriochlorins, in vivo studies using the N-[4-(5-nitro-2-furyl)-2-thiazolyl]-formamide-induced rat bladder tumor (AY-27) transplanted into Fisher CDF (F344)/CrlBr rats demonstrated a powerful photodynamic response.
Morgan
A R
AR
Department of Chemistry, University of Toledo, Ohio 43606.
Skalkos
D
D
Garbo
G M
GM
Keck
R W
RW
Selman
S H
SH
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D010778:Photochemotherapy; D011166:Porphyrins / Q000138:chemical synthesis* / Q000627:therapeutic use; D051381:Rats; D011916:Rats, Inbred F344; D013329:Structure-Activity Relationship; D001749:Urinary Bladder Neoplasms / Q000188:drug therapy*
D000970:Antineoplastic Agents; D011166:Porphyrins