Three azobisporphyrins (Por1, Por2 and Por3) were synthesized by coupling two molecules of (4-nitrophenyl/pyridyl) porphyrins in the presence of KOH/butanol. The structures of porphyrins were confirmed by UV, IR, NMR and mass spectra and elemental analysis. With tetraphenylporphyrin (H2TPP) as a control, the singlet oxygen (1O[Formula: see text] generation of porphyrins was evaluated through 1,3-diphenylisobenzofuran (DPBF) method. The order of ability to generate 1O2 for three azobisporphyrins was Por 1 [Formula: see text]Por 2 > Por 3[Formula: see text] H2TPP. The photocytotoxicity and sub-cellular localization of azobisporphyrins over Hela cells were studied through MTT analysis and confocal laser scanning microscope, respectively. The results indicated Por 1 and Por 2 displayed the low dark-cytotoxicity, while Por 3 induced a concentration-dependent cytotoxicity to Hela cells with the concentration of porphyrins ranging from 1 to 100 [Formula: see text] M. With the light dose at 4 J/cm2, Por 3 killed more than 60% Hela cells at 2 [Formula: see text] M, indicating a high photocytoxicity. As seen from the laser scanning confocal microscopy images, Por 3 was mainly localized in cell membrane, while Por 1 and Por 2 do not displayed significant fluorescent emission in Hela cells. These results suggest the synthesized cationic azobisporphyrin could be used as a potential therapeutic agent for photodynamic therapy of cancers.

中文翻译：

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偶氮双卟啉的合成、单线态氧产生、光细胞毒性和亚细胞定位作为潜在的光动力治疗剂体外细胞研究

通过在 KOH/丁醇存在下偶联两分子 (4-硝基苯基/吡啶基) 卟啉合成了三种偶氮二卟啉 (Por1、Por2 和 Por3)。卟啉的结构经紫外、红外、核磁共振、质谱和元素分析证实。与四苯基卟啉（H2TPP）作为对照，单线态氧（1O[公式：见正文]通过1,3-二苯基异苯并呋喃(DPBF)法评价卟啉的生成。生成能力的顺序1○2对于三种偶氮二卟啉，Por 1 [公式：见正文]Por 2 > Por 3[公式：见正文] H2跨太平洋伙伴关系协定。分别通过MTT分析和共聚焦激光扫描显微镜研究了偶氮双卟啉对Hela细胞的光细胞毒性和亚细胞定位。结果表明Por 1和Por 2表现出较低的暗细胞毒性，而Por 3对Hela细胞产生浓度依赖性细胞毒性，卟啉浓度范围为1-100 [公式：见正文] M。 4 焦耳/厘米2, Por 3 在 2 [公式：见正文] M 时杀死 60% 以上的 Hela 细胞，表明具有高光细胞毒性。从激光扫描共聚焦显微镜图像中可以看出，Por 3 主要位于细胞膜中，而 Por 1 和 Por 2 在 Hela 细胞中没有显示出显着的荧光发射。这些结果表明，合成的阳离子偶氮二卟啉可用作癌症光动力治疗的潜在治疗剂。