Photodynamic therapy (PDT) has been developed as a promising therapeutic method in cancer treatment. The discovery of effective photosensitizer, which is the key factor of PDT, is highly desired. This paper reports the synthesis of novel chlorin derivatives, 5,10,15,20-tetraphenyl-[2:3]-[(methoxycarbonyl, carboxy)methano] chlorin I and 5,10,15,20-tetraphenyl-[2:3]- {[methoxycarbonyl, (2-hydroxyethyl)amide]methano}chlorin II. Their structures were characterized with UV-vis, 1HNMR, 13CNMR and HRMS spectroscopies. Photophysical and photochemical experiments results showed that compound I and II had an absorption maximum around 650 nm, with molar extinction coefficients of 1 × 104 M-1 cm-1. They had strong fluorescence emission in 650-660 nm upon excitation with 419-422 nm light. ESR showed that singlet oxygen was produced upon irradiation of compounds with 650 nm light in the presence of molecular oxygen. The photo-bleaching test indicated that the structure of compounds was stable. These new compounds exhibit excellent anti-tumor effects and lower toxicity compared to m-THPC in vitro and in vivo. Compound I and II had high tumor selectivity, which could induced tumor cells shrinkage and necrosis under 650 nm laser irradiation. Flow cytometry revealed that the compounds might mediate PDT effect at late apoptotic phase. These results make these compound I and II promising candidates for future study in photo-diagnosis and photodynamic therapy of cholangiocarcinoma.

中文翻译：

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二氢卟酚衍生物的合成及其药理学评价对胆管癌的光动力治疗。

光动力疗法（PDT）已被开发为一种有前途的癌症治疗方法。迫切需要发现有效的光敏剂，它是PDT的关键因素。本文报道了新型二氢卟酚衍生物5,10,15,20-四苯基-[2：3]-[（甲氧羰基，羧基）甲氧基]二氢卟酚I和5,10,15,20-四苯基-[2： 3]-{[甲氧基羰基，（2-羟乙基）酰胺]亚甲基}二氢卟酚II。用紫外可见，1 HNMR，13 C NMR和HRMS光谱对它们的结构进行了表征。光物理和光化学实验结果表明，化合物I和II在650 nm附近具有最大吸收，摩尔消光系数为1×104 M-1 cm-1。当用419-422 nm的光激发时，它们在650-660 nm处具有很强的荧光发射。ESR表明在分子氧存在下用650 nm光照射化合物会产生单线态氧。光漂白测试表明化合物的结构是稳定的。与m-THPC体外和体内相比，这些新化合物具有出色的抗肿瘤作用和较低的毒性。化合物I和II具有较高的肿瘤选择性，可以在650 nm激光照射下诱导肿瘤细胞缩小和​​坏死。流式细胞仪显示这些化合物可能在细胞凋亡的后期介导PDT的作用。这些结果使得这些化合物I和II有望在胆管癌的光诊断和光动力疗法的未来研究中有希望。与m-THPC体外和体内相比，这些新化合物具有出色的抗肿瘤作用和较低的毒性。化合物I和II具有较高的肿瘤选择性，可以在650 nm激光照射下诱导肿瘤细胞缩小和​​坏死。流式细胞仪显示这些化合物可能在细胞凋亡的后期介导PDT的作用。这些结果使得这些化合物I和II有望在胆管癌的光诊断和光动力疗法的未来研究中有希望。与m-THPC体外和体内相比，这些新化合物具有出色的抗肿瘤作用和较低的毒性。化合物I和II具有较高的肿瘤选择性，可以在650 nm激光照射下诱导肿瘤细胞缩小和​​坏死。流式细胞仪显示这些化合物可能在细胞凋亡的后期介导PDT的作用。这些结果使得这些化合物I和II有望在胆管癌的光诊断和光动力疗法的未来研究中有希望。