BODIPY-Based Fluorometric Sensor for the Simultaneous Determination of Cys, Hcy, and GSH in Human Serum

ACS Applied Materials and Interfaces

Volumn 7, Issue 10, 2015, Pages 5907-5914

  Jia, Ming Yan ^a,c   Niu, Li Ya ^b   Zhang, Yu ^a   Yang, Qing Zheng ^b   Tung, Chen Ho ^b   Guan, Ya Feng ^a   Feng, Liang ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

BODIPY; cysteine; glutathione; homocysteine; serum

Indexed keywords

DIES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDES; SUBSTITUTION REACTIONS; SULFUR;

BODIPY; CYSTEINE; GLUTATHIONES; HOMOCYSTEINES; SERUM;

AMINO ACIDS;

4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; CYSTEINE; DRUG MIXTURE; GLUTATHIONE; HOMOCYSTEINE;

BLOOD; BLOOD ANALYSIS; CHEMISTRY; DEVICE FAILURE ANALYSIS; DEVICES; DRUG MIXTURE; EQUIPMENT DESIGN; EVALUATION STUDY; FLUOROMETRY; GENETIC PROCEDURES; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY;

BIOSENSING TECHNIQUES; BLOOD CHEMICAL ANALYSIS; BORON COMPOUNDS; COMPLEX MIXTURES; CYSTEINE; EQUIPMENT DESIGN; EQUIPMENT FAILURE ANALYSIS; FLUOROMETRY; GLUTATHIONE; HOMOCYSTEINE; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY;

EID: 84925358445     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b00122     Document Type: Article

References (43)

1. Miller, J. W.; Beresford, S. A. A.; Neuhouser, M. L.; Cheng, T. Y. D.; Song, X.; Brown, E. C.; Zheng, Y.; Rodriguez, B.; Green, R.; Ulrieh, C. M. Homocysteine, Cysteine, and Risk of Incident Colorectal Cancer in the Women's Health Initiative Observational Cohort Am. J. Clin. Nutr. 2013, 97, 827-834
2. Shahrokhian, S. Lead Phthalocyanine as a Selective Carrier for Preparation of a Cysteine-Selective Electrode Anal. Chem. 2001, 73, 5972-5978
3. Refsum, H.; Smith, A. D.; Ueland, P. M.; Nexo, E.; Clarke, R.; McPartlin, J.; Johnston, C.; Engbaek, F.; Schneede, J.; McPartlin, C.; Scott, J. M. Facts and Recommendations about Total Homocysteine Determinations: An Expert Opinion Clin. Chem. 2004, 50, 3-32
4. Townsend, D. M.; Tew, K. D.; Tapiero, H. The Importance of Glutathione in Human Disease Biomed. Pharmacother. 2003, 57, 145-155
5. Chen, X.; Zhou, Y.; Peng, X.; Yoon, J. Fluorescent and Colorimetric Probes for Detection of Thiols Chem. Soc. Rev. 2010, 39, 2120-2135
6. Jung, H. S.; Chen, X.; Kim, J. S.; Yoon, J. Recent Progress in Luminescent and Colorimetric Chemosensors for Detection of Thiols Chem. Soc. Rev. 2013, 42, 6019-6031
7. Tang, B.; Xing, Y. L.; Li, P.; Zhang, N.; Yu, F. B.; Yang, G. W. Rhodamine-Based Fluorescent Probe Containing a Se-N Bond for Detecting Thiols and Its Application in Living Cells J. Am. Chem. Soc. 2007, 129, 11666-11667
8. Yi, L.; Li, H.; Sun, L.; Liu, L.; Zhang, C.; Xi, Z. A Highly Sensitive Fluorescence Probe for Fast Thiol-Quantification Assay of Glutathione Reductase Angew. Chem., Int. Ed. 2009, 48, 4034-4037
9. Lee, M. H.; Han, J. H.; Kwon, P. S.; Bhuniya, S.; Kim, J. Y.; Sessler, J. L.; Kang, C.; Kim, J. S. Hepatocyte-Targeting Single Galactose-Appended Naphthalimide: A Tool for Intracellular Thiol Imaging in Vivo J. Am. Chem. Soc. 2012, 134, 1316-1322
10. McMahon, B. K.; Gunnlaugsson, T. Selective Detection of the Reduced Form of Glutathione (GSH) over the Oxidized (GSSG) Form Using a Combination of Glutathione Reductase and a Tb(III)-Cyclen Maleimide Based Lanthanide Luminescent 'Switch On' Assay J. Am. Chem. Soc. 2012, 134, 10725-10728
11. Guy, J.; Caron, K.; Dufresne, S.; Michnick, S. W.; Skene, W. G.; Keillor, J. W. Convergent Preparation and Photophysical Characterization of Dimaleimide Dansyl Fluorogens: Elucidation of the Maleimide Fluorescence Quenching Mechanism J. Am. Chem. Soc. 2007, 129, 11969-11977
12. Shao, J.; Sun, H.; Guo, H.; Ji, S.; Zhao, J.; Wu, W.; Yuan, X.; Zhang, C.; James, T. D. A Highly Selective Red-Emitting FRET Fluorescent Molecular Probe Derived from BODIPY for the Detection of Cysteine and Homocysteine: An Experimental and Theoretical Study Chem. Sci. 2012, 3, 1049-1061
13. Zhang, M.; Yu, M.; Li, F.; Zhu, M.; Li, M.; Gao, Y.; Li, L.; Liu, Z.; Zhang, J.; Zhang, D.; Yi, T.; Huang, C. A Highly Selective Fluorescence Turn-On Sensor for Cysteine/Homocysteine and Its Application in Bioimaging J. Am. Soc. Chem. 2007, 129, 10322-10323
14. Li, H.; Fan, J.; Wang, J.; Tian, M.; Du, J.; Sun, S.; Sun, P.; Peng, X. A Fluorescent Chemodosimeter Specific for Cysteine: Effective Discrimination of Cysteine from Homocysteine Chem. Commun. 2009, 5904-5906
15. Yang, X.; Guo, Y.; Strongin, R. M. Conjugate Addition/Cyclization Sequence Enables Selective and Simultaneous Fluorescence Detection of Cysteine and Homocysteine Angew. Chem., Int. Ed. 2011, 50, 10690-10693
16. Guo, Z.; Nam, S.; Park, S.; Yoon, J. A Highly Selective Ratiometric Near-Infrared Fluorescent Cyanine Sensor for Cysteine with Remarkable Shift and Its Application in Bioimaging Chem. Sci. 2012, 3, 2760-2765
17. Kong, F.; Liu, R.; Chu, R.; Wang, X.; Xu, K.; Tang, B. A Highly Sensitive Near-Infrared Fluorescent Probe for Cysteine and Homocysteine in Living Cells Chem. Commun. 2013, 49, 9176-9178
18. Niu, L.-Y.; Guan, Y.-S.; Chen, Y.-Z.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. A Turn-On Fluorescent Sensor for the Discrimination of Cystein from Homocystein and Glutathione Chem. Commun. 2013, 49, 1294-1296
19. Wu, S.; Song, H.; Song, J.; He, C.; Ni, J.; Zhao, Y.; Wang, X. Development of Triphenylamine Functional Dye for Selective Photoelectrochemical Sensing of Cysteine Anal. Chem. 2014, 86, 5922-5928
20. Yuan, X.; Tay, Y.; Dou, X.; Luo, Z.; Leong, D. T.; Xie, J. Glutathione-Protected Silver Nanoclusters as Cysteine-Selective Fluorometric and Colorimetric Probe Anal. Chem. 2013, 85, 1913-1919
21. Wang, W. H.; Escobedo, J. O.; Lawrence, C. M.; Strongin, R. M. Direct Detection of Homocysteine J. Am. Chem. Soc. 2004, 126, 3400-3401
22. Chen, H.; Zhao, Q.; Wu, Y.; Li, F.; Yang, H.; Yi, T.; Huang, C. Selective Phosphorescence Chemosensor for Homocysteine Based on an Iridium(III) Complex Inorg. Chem. 2007, 46, 11075-11081
23. Hakuna, L.; Escobedo, J. O.; Lowry, M.; Barve, A.; McCallum, N.; Strongin, R. M. A Photochemical Method for Determining Plasma Homocysteine with Limited Sample Processing Chem. Commun. 2014, 50, 3071-3073
24. Lee, H. Y.; Choi, Y. P.; Kim, S.; Yoon, T.; Guo, Z.; Lee, S.; Swamy, K. M. K.; Kim, G.; Lee, J. Y.; Shin, I.; Yoon, J. Selective Homocysteine Turn-On Fluorescent Probes and Their Bioimaging Applications Chem. Commun. 2014, 50, 6967-6969
25. Shao, N.; Jin, J.; Wang, H.; Zheng, J.; Yang, R.; Chan, W.; Abliz, Z. Design of Bis-spiropyran Ligands as Dipolar Molecule Receptors and Application to in Vivo Glutathione Fluorescent Probes J. Am. Chem. Soc. 2010, 132, 725-736
26. Niu, L.-Y.; Guan, Y.-S.; Chen, Y.-Z.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine J. Am. Chem. Soc. 2012, 134, 18928-18931
27. Lim, S.-Y.; Hong, K.-H.; Kim, D. I.; Kwon, H.; Kim, H.-J. Tunable Heptamethine-Azo Dye Conjugate as an NIR Fluorescent Probe for the Selective Detection of Mitochondrial Glutathione over Cysteine and Homocysteine J. Am. Chem. Soc. 2014, 136, 7018-7025
28. Yin, J.; Kwon, Y.; Kim, D.; Lee, D.; Kim, G.; Hu, Y.; Ryu, J.-H.; Yoon, J. Cyanine-Based Fluorescent Probe for Highly Selective Detection of Glutathione in Cell Cultures and Live Mouse Tissues J. Am. Chem. Soc. 2014, 136, 5351-5358
29. Liu, J.; Sun, Y.-Q.; Huo, Y.; Zhang, H.; Wang, L.; Zhang, P.; Song, D.; Shi, Y.; Guo, W. Simultaneous Fluorescence Sensing of Cys and GSH from Different Emission Channels J. Am. Chem. Soc. 2014, 136, 574-577
30. Liu, J.; Sun, Y.-Q.; Zhang, H.; Huo, Y.; Shi, Y.; Guo, W. Simultaneous Fluorescent Imaging of Cys/Hcy and GSH from Different Emission Channels Chem. Sci. 2014, 5, 3183-3188
31. Yang, X.-F.; Huang, Q.; Zhong, Y.; Li, Z.; Li, H.; Lowry, M.; Escobedo, J. O.; Strongin, R. M. A Dual Emission Fluorescent Probe Enables Simultaneous Detection of Glutathione and Cysteine/Homocysteine Chem. Sci. 2014, 5, 2177-2183
32. Wang, F.; Guo, Z.; Li, X.; Li, X.; Zhao, C. Development of a Small Molecule Probe Capable of Discriminating Cysteine, Homocysteine, and Glutathione with Three Distinct Turn-On Fluorescent Outputs Chem.-Eur. J. 2014, 20, 11471-11478
33. Wang, W. H.; Rusin, O.; Xu, X. Y.; Kim, K. K.; Escobedo, J. O.; Fakayode, S. O.; Fletcher, K. A.; Lowry, M.; Schowalter, C. M.; Lawrence, C. M.; Fronczek, F. R.; Warner, I. M.; Strongin, R. M. Detection of Homocysteine and Cysteine J. Am. Chem. Soc. 2005, 127, 15949-15958
34. Baruah, M.; Qin, W.; Basarić, N.; De Borggraeve, W. M.; Boens, N. BODIPY-Based Hydroxyaryl Derivatives as Fluorescent pH Probes J. Org. Chem. 2005, 70, 4152-4157
35. Domaille, D. W.; Zeng, L.; Chang, C. J. Visualizing Ascorbate-Triggered Release of Labile Copper within Living Cells using a Ratiometric Fluorescent Sensor J. Am. Chem. Soc. 2010, 132, 1194-1195
36. Ferin, R.; Pavão, M. L.; Baptista, J. Methodology for a Rapid and Simultaneous Determination of Total Cysteine, Homocysteine, Cysteinylglycine and Glutathione in Plasma by Isocratic RP-HPLC J. Chromatogr. B 2012, 911, 15-20
37. Kobayashi, T.; Komatsu, T.; Kamiya, M.; Campos, C.; González-Gaitán, M.; Terai, T.; Hanaoka, K.; Nagano, T.; Urano, Y. Highly Activatable and Environment-Insensitive Optical Highlighters for Selective Spatiotemporal Imaging of Target Proteins J. Am. Chem. Soc. 2012, 134, 11153-11160
38. Boens, N.; Leen, V.; Dehaen, W. Fluorescent Indicators Based on BODIPY Chem. Soc. Rev. 2012, 41, 1130-1172
39. Ulrich, G.; Ziessel, R.; Harriman, A. The Chemistry of Fluorescent BODIPY Dyes: Versatility Unsurpassed Angew. Chem., Int. Ed. 2008, 47, 1184-1201
40. Loudet, A.; Burgess, K. BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties Chem. Rev. 2007, 107, 4891-4932
41. Jacobsen, D. W.; Gatautis, V. J.; Green, R.; Robinson, K.; Savon, S. R.; Secic, M.; Ji, J.; Otto, J. M.; Taylor, L. M. Rapid HPLC Determination of Total Homocysteine and Other Thiols in Serum and Plasma: Sex Differences and Correlation with Cobalamin and Folate Concentrations in Healthy Subjects Clin. Chem. 1994, 40, 873-881
42. Morrison, J. A.; Jacobsen, D. W.; Sprecher, D. L.; Robinson, K.; Khoury, P.; Daniels, S. R. Serum Glutathione in Adolescent Males Predicts Parental Coronary Heart Disease Circulation 1999, 100, 2244-2247
43. El-Khairy, L.; Ueland, P. M.; Refsum, H.; Graham, I. M.; Vollset, S. E. Plasma Total Cysteine as a Risk Factor for Vascular Disease-The European Concerted Action Project Circulation 2001, 103, 2544-2549