酞菁-生物素缀合物的合成与研究
Synthesis and investigation of phthalocyanine-biotin conjugates.
作者信息
Okoth Elizabeth A, Zhou Zehua, Ongarora Benson, Stutes Alyssa, Mathis J Michael, Vicente M Graça H
机构信息
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
Department of Comparative Biomedical Sciences, Louisiana State University School of Veterinary Medicine, Baton Rouge Louisiana 70803, USA.
出版信息
J Porphyr Phthalocyanines. 2019;23(1n02):125-135. doi: 10.1142/s1088424619500056.
An isothiocyanato-functionalized phthalocyanine (Pc) was synthesized in good yield from the corresponding amine-substituted Pc. This Pc reacted with ethanolamine, biotin hydrazine, and biotin diethylamine under mild conditions (room temperature in DMF or DMSO in the presence of TEA) to produce the corresponding thiourea products in 60-75% yields. All Pcs showed intense Q absorptions in DMF around 677 nm, emissions centered at 683 nm, and fluorescence quantum yields in the range 0.18-0.27. The Pcs were phototoxic to human carcinoma HEp2 cells (IC ~ 7 at 1.5 J/cm) and localized in multiple organelles, including the lysosomes, Golgi and ER. One biotin-Pc conjugate was injected tail vein into nude mice bearing HT-29 tumors and demonstrated selective localization in the tumor tissue.
通过相应的胺取代酞菁以良好的产率合成了异硫氰酸酯官能化的酞菁（Pc）。该酞菁在温和条件下（室温，在DMF或DMSO中，在三乙胺存在下）与乙醇胺、生物素肼和生物素二乙胺反应，以60 - 75%的产率生成相应的硫脲产物。所有的酞菁在DMF中于677 nm左右显示出强烈的Q吸收，发射峰位于683 nm，荧光量子产率在0.18 - 0.27范围内。这些酞菁对人肝癌HEp2细胞具有光毒性（在1.5 J/cm²时IC₅₀约为7），并定位于包括溶酶体、高尔基体和内质网在内的多个细胞器中。一种生物素 - Pc缀合物通过尾静脉注射到携带HT - 29肿瘤的裸鼠体内，并在肿瘤组织中显示出选择性定位。
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