Synthesis of taurine-fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro

作     者：Meihong Huang Jiaqi Song Bingzheng Lu Huizhi Huang Yizhen Chen Wei Yin Wenbo Zhu Xinwen Su Chuanbin Wu Haiyan Hu 

作者机构：Laboratory of PharmaceuticsSchool of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China Pharmacy Department of Guangxi Minzu HospitalNanning 530001China Department of PharmacologyZhongshan School of MedicineSun Yat-sen UniversityGuangzhou 510080China 

出 版 物：《Acta Pharmaceutica Sinica B》 (药学学报（英文版）)

年 卷 期：2014年第4卷第6期

页      面：447-453页

核心收录：

学科分类：1007[医学-药学(可授医学、理学学位)] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

主　　题：Taurine Taurine-fluorescein con-jugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability 

摘      要：In this work, retinal penetration of fluorescein was achieved in vitro by covalent attachment of taurine to fluorescein, yielding the F-Tau conjugate. Nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS) were used to confirm the successful synthesis of F-Tau. The cellular uptake of F-Tau in adult retinal pigment epithelial cells (ARPE-19) and human retinal microvascular endothelial cells (hRMECs) was visualized via confocal scanning microscopy. The results indicated an improvement of solubility and a reduction of logP of F-Tau compared with fluorescein. As compared with fluorescein, F-Tau showed little toxicity, and was retained longer by cells in uptake experiments. F-Tau also displayed higher transepithelial permeabilities than fluorescein in ARPE-19 and hRMECs monolayer cells (Po0.05). These results showed that taurine may be a useful ligand for targeting small-molecule hydrophobic pharmaceuticals into the retina.