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

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 up...
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Autor*in:	Meihong Huang [verfasserIn] Jiaqi Song [verfasserIn] Bingzheng Lu [verfasserIn] Huizhi Huang [verfasserIn] Yizhen Chen [verfasserIn] Wei Yin [verfasserIn] Wenbo Zhu [verfasserIn] Xinwen Su [verfasserIn] Chuanbin Wu [verfasserIn] Haiyan Hu [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2014

Schlagwörter:	Taurine Taurine–fluorescein conjugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability

Übergeordnetes Werk:	In: Acta Pharmaceutica Sinica B - Elsevier, 2013, 4(2014), 6, Seite 447-453
Übergeordnetes Werk:	volume:4 ; year:2014 ; number:6 ; pages:447-453

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc Journal toc

DOI / URN:	10.1016/j.apsb.2014.10.006

Katalog-ID:	DOAJ028288947

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spelling	10.1016/j.apsb.2014.10.006 doi (DE-627)DOAJ028288947 (DE-599)DOAJ20f0a2ba471d49abb6f1b54719ffb9ee DE-627 ger DE-627 rakwb eng RM1-950 Meihong Huang verfasserin aut Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. Taurine Taurine–fluorescein conjugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability Therapeutics. Pharmacology Jiaqi Song verfasserin aut Bingzheng Lu verfasserin aut Huizhi Huang verfasserin aut Yizhen Chen verfasserin aut Wei Yin verfasserin aut Wenbo Zhu verfasserin aut Xinwen Su verfasserin aut Chuanbin Wu verfasserin aut Haiyan Hu verfasserin aut In Acta Pharmaceutica Sinica B Elsevier, 2013 4(2014), 6, Seite 447-453 (DE-627)670211095 (DE-600)2631779-5 22113843 nnns volume:4 year:2014 number:6 pages:447-453 https://doi.org/10.1016/j.apsb.2014.10.006 kostenfrei https://doaj.org/article/20f0a2ba471d49abb6f1b54719ffb9ee kostenfrei http://www.sciencedirect.com/science/article/pii/S2211383514001051 kostenfrei https://doaj.org/toc/2211-3835 Journal toc kostenfrei https://doaj.org/toc/2211-3843 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2014 6 447-453
allfields_unstemmed	10.1016/j.apsb.2014.10.006 doi (DE-627)DOAJ028288947 (DE-599)DOAJ20f0a2ba471d49abb6f1b54719ffb9ee DE-627 ger DE-627 rakwb eng RM1-950 Meihong Huang verfasserin aut Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. Taurine Taurine–fluorescein conjugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability Therapeutics. Pharmacology Jiaqi Song verfasserin aut Bingzheng Lu verfasserin aut Huizhi Huang verfasserin aut Yizhen Chen verfasserin aut Wei Yin verfasserin aut Wenbo Zhu verfasserin aut Xinwen Su verfasserin aut Chuanbin Wu verfasserin aut Haiyan Hu verfasserin aut In Acta Pharmaceutica Sinica B Elsevier, 2013 4(2014), 6, Seite 447-453 (DE-627)670211095 (DE-600)2631779-5 22113843 nnns volume:4 year:2014 number:6 pages:447-453 https://doi.org/10.1016/j.apsb.2014.10.006 kostenfrei https://doaj.org/article/20f0a2ba471d49abb6f1b54719ffb9ee kostenfrei http://www.sciencedirect.com/science/article/pii/S2211383514001051 kostenfrei https://doaj.org/toc/2211-3835 Journal toc kostenfrei https://doaj.org/toc/2211-3843 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2014 6 447-453
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allfieldsSound	10.1016/j.apsb.2014.10.006 doi (DE-627)DOAJ028288947 (DE-599)DOAJ20f0a2ba471d49abb6f1b54719ffb9ee DE-627 ger DE-627 rakwb eng RM1-950 Meihong Huang verfasserin aut Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. Taurine Taurine–fluorescein conjugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability Therapeutics. Pharmacology Jiaqi Song verfasserin aut Bingzheng Lu verfasserin aut Huizhi Huang verfasserin aut Yizhen Chen verfasserin aut Wei Yin verfasserin aut Wenbo Zhu verfasserin aut Xinwen Su verfasserin aut Chuanbin Wu verfasserin aut Haiyan Hu verfasserin aut In Acta Pharmaceutica Sinica B Elsevier, 2013 4(2014), 6, Seite 447-453 (DE-627)670211095 (DE-600)2631779-5 22113843 nnns volume:4 year:2014 number:6 pages:447-453 https://doi.org/10.1016/j.apsb.2014.10.006 kostenfrei https://doaj.org/article/20f0a2ba471d49abb6f1b54719ffb9ee kostenfrei http://www.sciencedirect.com/science/article/pii/S2211383514001051 kostenfrei https://doaj.org/toc/2211-3835 Journal toc kostenfrei https://doaj.org/toc/2211-3843 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2014 6 447-453
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topic_facet	Taurine Taurine–fluorescein conjugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability Therapeutics. Pharmacology
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authorswithroles_txt_mv	Meihong Huang @@aut@@ Jiaqi Song @@aut@@ Bingzheng Lu @@aut@@ Huizhi Huang @@aut@@ Yizhen Chen @@aut@@ Wei Yin @@aut@@ Wenbo Zhu @@aut@@ Xinwen Su @@aut@@ Chuanbin Wu @@aut@@ Haiyan Hu @@aut@@
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callnumber-first	R - Medicine
author	Meihong Huang
spellingShingle	Meihong Huang misc RM1-950 misc Taurine misc Taurine–fluorescein conjugate misc Retina-targeting misc ARPE-19 misc hRMECs misc Transepithelial permeability misc Therapeutics. Pharmacology Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro
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topic_title	RM1-950 Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro Taurine Taurine–fluorescein conjugate Retina-targeting ARPE-19 hRMECs Transepithelial permeability
topic	misc RM1-950 misc Taurine misc Taurine–fluorescein conjugate misc Retina-targeting misc ARPE-19 misc hRMECs misc Transepithelial permeability misc Therapeutics. Pharmacology
topic_unstemmed	misc RM1-950 misc Taurine misc Taurine–fluorescein conjugate misc Retina-targeting misc ARPE-19 misc hRMECs misc Transepithelial permeability misc Therapeutics. Pharmacology
topic_browse	misc RM1-950 misc Taurine misc Taurine–fluorescein conjugate misc Retina-targeting misc ARPE-19 misc hRMECs misc Transepithelial permeability misc Therapeutics. Pharmacology
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title	Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro
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title_full	Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro
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author_browse	Meihong Huang Jiaqi Song Bingzheng Lu Huizhi Huang Yizhen Chen Wei Yin Wenbo Zhu Xinwen Su Chuanbin Wu Haiyan Hu
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title_sort	synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro
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title_auth	Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro
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.
abstractGer	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.
abstract_unstemmed	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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title_short	Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro
url	https://doi.org/10.1016/j.apsb.2014.10.006 https://doaj.org/article/20f0a2ba471d49abb6f1b54719ffb9ee http://www.sciencedirect.com/science/article/pii/S2211383514001051 https://doaj.org/toc/2211-3835 https://doaj.org/toc/2211-3843
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author2	Jiaqi Song Bingzheng Lu Huizhi Huang Yizhen Chen Wei Yin Wenbo Zhu Xinwen Su Chuanbin Wu Haiyan Hu
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up_date	2024-07-03T16:45:58.726Z
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Synthesis of taurine–fluorescein conjugate and evaluation of its retina-targeted efficiency in vitro

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