1.Synthesis of taurine-fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro.
Meihong HUANG ; Jiaqi SONG ; Bingzheng LU ; Huizhi HUANG ; Yizhen CHEN ; Wei YIN ; Wenbo ZHU ; Xinwen SU ; Chuanbin WU ; Haiyan HU
Acta Pharmaceutica Sinica B 2014;4(6):447-453
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 (P<0.05). These results showed that taurine may be a useful ligand for targeting small-molecule hydrophobic pharmaceuticals into the retina.
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