Morgan A R, Skalkos D, Garbo G M, Keck R W, Selman S H
Department of Chemistry, University of Toledo, Ohio 43606.
J Med Chem. 1991 Jul;34(7):2126-33. doi: 10.1021/jm00111a031.
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.
细菌叶绿素已被提议作为光动力疗法中潜在的光敏剂。我们已经表明，类似细菌叶绿素的大环化合物可以通过5,10-或5,15-双[（乙氧基羰基）乙烯基]卟啉的环化反应生成；然而，所得产物在暴露于空气中时会迅速分解。通过亲双烯体（如乙酰基二羧酸二甲酯或四氰基乙烯）与乙烯基卟啉酮之间的狄尔斯-阿尔德反应，可以生成更稳定的体系。尽管这些后一种产物的光谱性质类似于卟啉酮而非细菌叶绿素，但在将N-[4-（5-硝基-2-呋喃基）-2-噻唑基]-甲酰胺诱导的大鼠膀胱肿瘤（AY-27）移植到Fisher CDF（F344）/CrlBr大鼠体内的体内研究中，显示出了强大的光动力反应。
