Synthesis of taurine-fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro.
10.1016/j.apsb.2014.10.006
- Author:
Meihong HUANG
1
,
2
;
Jiaqi SONG
3
;
Bingzheng LU
4
;
Huizhi HUANG
3
;
Yizhen CHEN
3
;
Wei YIN
4
;
Wenbo ZHU
4
;
Xinwen SU
4
;
Chuanbin WU
3
;
Haiyan HU
3
Author Information
1. Laboratory of Pharmaceutics, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
2. Pharmacy Department of Guangxi Minzu Hospital, Nanning 530001, China.
3. Laboratory of Pharmaceutics, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
4. Department of Pharmacology, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou 510080, China.
- Publication Type:Journal Article
- Keywords:
ARPE-19;
Retina-targeting;
Taurine;
Taurine–fluorescein conjugate;
Transepithelial permeability;
hRMECs
- From:
Acta Pharmaceutica Sinica B
2014;4(6):447-453
- CountryChina
- Language:English
-
Abstract:
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.
