Differences in heterocycle basicity distinguish homocysteine from cysteine using aldehyde-bearing fluorophores

被引:63
作者
Barve, Aabha [1 ]
Lowry, Mark [1 ]
Escobedo, Jorge O. [1 ]
Huynh, Katherine T. [1 ]
Hakuna, Lovemore [1 ]
Strongin, Robert M. [1 ]
机构
[1] Portland State Univ, Dept Chem, Portland, OR 97207 USA
基金
美国国家卫生研究院;
关键词
HIGHLY SELECTIVE DETECTION; PLASMA HOMOCYSTEINE; FLUORESCENT SENSOR; THIOL COMPOUNDS; CYCLIC AMINES; GLUTATHIONE; DISEASE; PROBES; CHEMOSENSORS; AGGREGATION;
D O I
10.1039/c4cc03527e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the detection of homocysteine over cysteine based upon characteristic differences between 5- and 6-membered heterocyclic amines formed upon reaction with aldehyde-bearing compounds. Homocysteine-derived thiazinane-4-carboxylic acids are more basic than cysteine-derived thiazolidines-4-carboxylic acids. Fluorescence enhancement in response to homocysteine is achieved by tuning pH and excitation wavelength.
引用
收藏
页码:8219 / 8222
页数:4
相关论文
共 35 条
[11]   A photochemical method for determining plasma homocysteine with limited sample processing [J].
Hakuna, Lovemore ;
Escobedo, Jorge O. ;
Lowry, Mark ;
Barve, Aabha ;
McCallum, Naneki ;
Strongin, Robert M. .
CHEMICAL COMMUNICATIONS, 2014, 50 (23) :3071-3073
[12]   Recent progress in luminescent and colorimetric chemosensors for detection of thiols [J].
Jung, Hyo Sung ;
Chen, Xiaoqiang ;
Kim, Jong Seung ;
Yoon, Juyoung .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (14) :6019-6031
[13]   Highly selective fluorescent sensor for homocysteine and cysteine [J].
Kim, Tae-Ki ;
Lee, Dong-Nam ;
Kim, Hae-Jo .
TETRAHEDRON LETTERS, 2008, 49 (33) :4879-4881
[14]  
KIM TR, 1986, B KOR CHEM SOC, V7, P25
[15]   Selective homocysteine turn-on fluorescent probes and their bioimaging applications [J].
Lee, Hye Yeon ;
Choi, Yoon Pyo ;
Kim, Sunkyung ;
Yoon, Taejin ;
Guo, Zhiqian ;
Lee, Songyi ;
Swamy, K. M. K. ;
Kim, Gyoungmi ;
Lee, Jin Yong ;
Shin, Injae ;
Yoon, Juyoung .
CHEMICAL COMMUNICATIONS, 2014, 50 (53) :6967-6969
[16]   Fluorescence turn-on probe for homocysteine and cysteine in water [J].
Lee, Kyung-Sik ;
Kim, Tae-Ki ;
Lee, Jong Ho ;
Kim, Hae-Jo ;
Hong, Jong-In .
CHEMICAL COMMUNICATIONS, 2008, (46) :6173-6175
[17]   Simultaneous analysis of multiple aminothiols in human plasma by high performance liquid chromatography with fluorescence detection [J].
McMenamin, M. Elizabeth ;
Himmelfarb, Jonathan ;
Nolin, Thomas D. .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2009, 877 (28) :3274-3281
[18]   Discriminatory Detection of Cysteine and Homocysteine Based on Dialdehyde-Functionalized Aggregation-Induced Emission Fluorophores [J].
Mei, Ju ;
Wang, Yijia ;
Tong, Jiaqi ;
Wang, Jian ;
Qin, Anjun ;
Sun, Jing Zhi ;
Tang, Ben Zhong .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (02) :612-619
[19]   Discriminative fluorescence detection of cysteine, homocysteine and glutathione via reaction-dependent aggregation of fluorophore-analyte adducts [J].
Mei, Ju ;
Tong, Jiaqi ;
Wang, Jian ;
Qin, Anjun ;
Sun, Jing Zhi ;
Tang, Ben Zhong .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (33) :17063-17070
[20]   BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine [J].
Niu, Li-Ya ;
Guan, Ying-Shi ;
Chen, Yu-Zhe ;
Wu, Li-Zhu ;
Tung, Chen-Ho ;
Yang, Qing-Zheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (46) :18928-18931