Thiol-chromene click chemistry: A coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications

CORC > 武汉物理与数学研究所 > 中国科学院武汉物理与数学研究所 > 磁共振应用研究部

	Thiol-chromene click chemistry: A coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications
	Yang, Yutao 1,2; Huo, Fangjun 2; Yin, Caixia 1; Zheng, Anmin 3; Chao, Jianbin 2; Li, Yingqi 1; Nie, Zongxiu 4; Martinez-Manez, Ramon 5,6; Liu, Diansheng 2
刊名	BIOSENSORS & BIOELECTRONICS
	2013-09-15
卷号	47 页码:300-306
关键词	Click Thiol Coumarin-chromene Regenerable Bioimaging
英文摘要	The synthesis and characterization of a coumarin-chromene (8, 9-dihydro-2H-cyclopenta[b]pyrano[2,3-f]chromene-2,10(7aH)-dione) (1) derivative and its use for thiol chemosensing in water was reported. Experimental details showed 1 acts as a probe for the detection of thiols including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), whereas amino acids which do not contain thiols induced no changes in UV-vis spectra and fluorescence emission properties of 1. A possible detection mechanism is a nucleophilic attack of thiols to the a,p-unsaturated ketone in 1 that resulted in a fluorescent coumarin derivative. Further studies showed that 1-thiol derivatives can be applied to the design of regenerative chemodosimeters for Cu2+, Hg2+ and Cd2+ in water based on Mn+-promoted desulfurization and recovery of 1. Furthermore, the optical properties of the probe and its Cys-addition product were theoretically studied. The ability of probe 1 to detect thiols in living cells (HepG2 cells) via an enhancement of the fluorescence was proved. Moreover, the applicability of 1 for the direct determination of biorelevant thiols in a complex matrix such as human plasma was also demonstrated. (C) 2013 Elsevier B.V. All rights reserved.
WOS标题词	Science & Technology ; Life Sciences & Biomedicine ; Physical Sciences
类目[WOS]	Biophysics ; Biotechnology & Applied Microbiology ; Chemistry, Analytical ; Electrochemistry ; Nanoscience & Nanotechnology
研究领域[WOS]	Biophysics ; Biotechnology & Applied Microbiology ; Chemistry ; Electrochemistry ; Science & Technology - Other Topics
关键词[WOS]	FLUORESCENT-PROBE ; IN-VIVO ; COLORIMETRIC CHEMOSENSOR ; ULTRASENSITIVE DETECTION ; LIVING CELLS ; CYSTEINE ; GLUTATHIONE ; HOMOCYSTEINE ; MECHANISM ; SENSOR
收录类别	SCI
语种	英语
WOS记录号	WOS:000320481900044
公开日期	2015-07-14
内容类型	期刊论文
源URL	[http://ir.wipm.ac.cn/handle/112942/1539]
专题	武汉物理与数学研究所_磁共振应用研究部
作者单位	1.Shanxi Univ, Key Lab Chem Biol & Mol Engn, Minist Educ, Inst Mol Sci, Taiyuan 030006, Peoples R China 2.Shanxi Univ, Res Inst Appl Chem, Taiyuan 030006, Peoples R China 3.Chinese Acad Sci, Wuhan Ctr Magnet Resonance, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan Inst Phys & Math, Wuhan 430071, Peoples R China 4.Chinese Acad Sci, Inst Chem, Beijing 100190, Peoples R China 5.Univ Valencia, Ctr Interuniv Reconocimiento Mol & Desarrollo Tec, IDM, Unidad Mixta Univ Politecn Valencia, E-46003 Valencia, Spain 6.CIBER BBN, Zaragoza, Spain
推荐引用方式 GB/T 7714	Yang, Yutao,Huo, Fangjun,Yin, Caixia,et al. Thiol-chromene click chemistry: A coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications[J]. BIOSENSORS & BIOELECTRONICS,2013,47:300-306.
APA	Yang, Yutao.,Huo, Fangjun.,Yin, Caixia.,Zheng, Anmin.,Chao, Jianbin.,...&Liu, Diansheng.(2013).Thiol-chromene click chemistry: A coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications.BIOSENSORS & BIOELECTRONICS,47,300-306.
MLA	Yang, Yutao,et al."Thiol-chromene click chemistry: A coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications".BIOSENSORS & BIOELECTRONICS 47(2013):300-306.