Spizzirri P G, Hill J S, Kahl S B, Ghiggino K P
School of Chemistry, University of Melbourne, Parkville, Victoria, Australia.
Photochem Photobiol. 1996 Dec;64(6):975-83. doi: 10.1111/j.1751-1097.1996.tb01864.x.
The absorption and emission spectra, fluorescence quantum yields and lifetimes and triplet state properties of a boronated porphyrin, the tetrakiscarborane carboxylate ester of 2,4-(alpha, beta-dihydroxyethyl) deuteroporphyrin IX (BOPP), have been determined. This compound is an alternative photodynamic therapy (PDT) agent that exhibits highly selective tumor localization, with the potential to be used in conjunction with boron neutron capture therapy. The photophysical characteristics of BOPP are similar to other porphyrins and it exhibits marked aggregation and acid-base speciation under typical physiological conditions. In particular, protonation of the porphyrin imino (-N=) nitrogens occurs in the pH 5-7 region and influences the photophysical properties. Time-resolved confocal fluorescence imaging of the intracellular distribution of BOPP in C6 glioma cells indicates distinct subcellular localization and heterogeneity of emission. The results are interpreted and discussed in terms of the possible mechanisms for cellular uptake and localization.
已测定了一种硼化卟啉，即2,4-(α,β-二羟乙基) 去甲卟啉IX的四碳硼烷羧酸酯（BOPP）的吸收光谱和发射光谱、荧光量子产率和寿命以及三重态性质。该化合物是一种替代光动力疗法（PDT）药物，具有高度选择性的肿瘤定位能力，有可能与硼中子俘获疗法联合使用。BOPP的光物理特性与其他卟啉相似，并且在典型生理条件下表现出明显的聚集和酸碱形态变化。特别是，卟啉亚氨基（-N=）氮在pH 5 - 7区域发生质子化，并影响光物理性质。对C6胶质瘤细胞中BOPP细胞内分布的时间分辨共聚焦荧光成像表明其在亚细胞水平上有明显的定位和发射异质性。根据细胞摄取和定位的可能机制对结果进行了解释和讨论。
