A colorimetric and fluorescent probe for thiols based on 1, 8-naphthalimide and its application for bioimaging

Dyes and Pigments

Volumn 100, Issue 1, 2014, Pages 255-260

  Shi, Jinmin ^a   Wang, Yujiao ^a   Tang, Xiaoliang ^a   Liiu, Wei ^a   Jiang, Huie ^a   Dou, Wei ^a   Liu, Weisheng ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Bioimaging; Colorimetric; Fluorescent; Naphthalimide; Probe; Thiols

Indexed keywords

BIO-IMAGING; COLORIMETRIC; FLUORESCENT; NAPHTHALIMIDE; THIOLS;

AMINO ACIDS; CHEMICAL SENSORS; COLOR; COLORIMETRY; FLUORESCENCE;

PROBES;

EID: 84884767942     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.09.021     Document Type: Article

References (58)

1. R.L. Krauth-Siegel, H. Bauer, and R.H. Schirmer Dithiol proteins as guardians of the intracellular redox milieu in parasites: old and new drug targets in trypanosomes and malaria-causing plasmodia Angew Chem Int Ed 44 5 2005 690 715 (Pubitemid 40203977)
2. R. Ball, G. Courtney-Martin, and P. Pencharz The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans J Nutr 136 2006 1682s 1693s (Pubitemid 43765381)
3. R. Hong, G. Han, J.M. Fernandez, B.J. Kim, N.S. Forbes, and V.M. Rotello Glutathione-mediated delivery and release using monolayer protected nanoparticle carriers J Am Chem Soc 128 4 2006 1078 1079 (Pubitemid 43190611)
4. S. Seshadri, A. Beiser, J. Selhub, P.F. Jacques, I.H. Rosenberg, and R.B. D'Agostino Plasma homocysteine as a risk factor for dementia and Alzheimer's disease N Engl J Med 346 7 2002 476 483 (Pubitemid 34441738)
5. R. Njälsson, and S. Norgren Physiological and pathological aspects of GSH metabolism Acta Paediatr 94 2 2005 132 137 (Pubitemid 40343683)
6. S. Shahrokhian Lead phthalocyanine as a selective carrier for preparation of a cysteine-selective electrode Anal Chem 73 24 2001 5972 5978 (Pubitemid 34042214)
7. D.M. Townsend, K.D. Tew, and H. Tapiero The importance of glutathione in human disease Biomed Pharmacother 57 3-4 2003 145 155 (Pubitemid 36740460)
8. L.A. Herzenberg, S.C. De Rosa, J.G. Dubs, M. Roederer, M.T. Anderson, and S.W. Ela PNAS-1997-Herzenberg-1967-72.pdf Proc Natl Acad Sci 94 1997 1967 1972
9. H. Refsum, P.M. Ueland, O. Nygard, and S.E. Vollset Homocysteine and cardiovascular disease Annu Rev Med 49 1998 31 62 (Pubitemid 28197439)
10. A.R. Ivanov, I.V. Nazimov, and L.A. Baratova Qualitative and quantitative determination of biologically active low-molecular-mass thiols in human blood by reversed-phase high-performance liquid chromatography with photometry and fluorescence detection J Chromatogr A 870 1-2 2000 433 442 (Pubitemid 30077446)
11. Y.V. Tcherkas, and A.D. Denisenko Simultaneous determination of several amino acids, including homocysteine, cysteine and glutamic acid, in human plasma by isocratic reversed-phase high-performance liquid chromatography with fluorimetric detection J Chromatogr A 913 1-2 2001 309 313 (Pubitemid 32260995)
12. M.J. MacCoss, N.K. Fukagawa, and D.E. Matthews Measurement of homocysteine concentrations and stable isotope tracer enrichments in human plasma Anal Chem 71 20 1999 4527 4533
13. A.P. Vellasco, R. Haddad, M.N. Eberlin, and N.F. Hoehr Combined cysteine and homocysteine quantitation in plasma by trap and release membrane introduction mass spectrometry Analyst 127 8 2002 1050 1053
14. S. Fei, J. Chen, S. Yao, G. Deng, D. He, and Y. Kuang Electrochemical behavior of L-cysteine and its detection at carbon nanotube electrode modified with platinum Anal Biochem 339 1 2005 29 35 (Pubitemid 40342674)
15. W. Wang, L. Li, S. Liu, C. Ma, and S. Zhang Determination of physiological thiols by electrochemical detection with piazselenole and its application in rat breast cancer cells 4T-1 J Am Chem Soc 130 33 2008 10846 10847
16. T. Inoue, and J.R. Kirchhoff Determination of thiols by capillary electrophoresis with amperometric detection at a coenzyme pyrroloquinoline quinone modified electrode Anal Chem 74 6 2002 1349 1354 (Pubitemid 34233326)
17. G. Chen, L. Zhang, and J. Wang Miniaturized capillary electrophoresis system with a carbon nanotube microelectrode for rapid separation and detection of thiols Talanta 64 4 2004 1018 1023
18. Y. Zeng, G. Zhang, and D. Zhang A selective colorimetric chemosensor for thiols based on intramolecular charge transfer mechanism Anal Chim Acta 627 2 2008 254 257
19. N. Shao, J.Y. Jin, S.M. Cheung, R.H. Yang, W.H. Chan, and T. Mo A spiropyran-based ensemble for visual recognition and quantification of cysteine and homocysteine at physiological levels Angew Chem Int Ed 45 30 2006 4944 4948 (Pubitemid 44166125)
20. C. Zheng, S. Pu, G. Liu, B. Chen, and Y. Dai A highly selective colorimetric sensor for cysteine and homocysteine based on a new photochromic diarylethene Dyes Pigm 98 2 2013 280 285
21. J.V. Ros-Lis, B. Garcia, D. Jimenez, R. Martinez-Manez, F. Sancenon, and J. Soto Squaraines as fluoro-chromogenic probes for thiol-containing compounds and their application to the detection of biorelevant thiols J Am Chem Soc 126 13 2004 4064 4065 (Pubitemid 38453843)
22. W. Wang, J.O. Escobedo, C.M. Lawrence, and R.M. Strongin Direct detection of homocysteine J Am Chem Soc 126 11 2004 3400 3401 (Pubitemid 38366712)
23. J. Zhu, I. Dhimitruka, and D. Pei 5-(2-Aminoethyl)dithio-2-nitrobenzoate as a more base-stable alternative to Ellman's reagent Org Lett 6 21 2004 3809 3812 (Pubitemid 39421950)
24. X. Zhang, C. Li, X. Cheng, X. Wang, and B. Zhang A near-infrared croconium dye-based colorimetric chemodosimeter for biological thiols and cyanide anion Sens Actuators B 129 1 2008 152 157
25. Y. Guo, S. Shao, J. Xu, Y. Shi, and S. Jiang A specific colorimetric cysteine sensing probe based on dipyrromethane-TCNQ assembly Tetrahedron 45 34 2004 6477 6480 (Pubitemid 39091071)
26. M.S. Han, and D.H. Kim Rationally designed chromogenic chemosensor that detects cysteine in aqueous solution with remarkable selectivity Tetrahedron 60 49 2004 11251 11257 (Pubitemid 39429486)
27. W. Jiang, Q. Fu, H. Fan, J. Ho, and W. Wang A highly selective fluorescent probe for thiophenols Angew Chem Int Ed 46 44 2007 8445 8448 (Pubitemid 350114957)
28. H. Maeda, H. Matsuno, M. Ushida, K. Katayama, K. Saeki, and N. Itoh 2,4-Dinitrobenzenesulfonyl fluoresceins as fluorescent alternatives to Ellman's reagent in thiol-quantification enzyme assays Angew Chem Int Ed 44 19 2005 2922 2925 (Pubitemid 40689674)
29. L. Long, W. Lin, B. Chen, W. Gao, and L. Yuan Construction of a FRET-based ratiometric fluorescent thiol probe Chem Commun 47 3 2011 893 895
30. M.H. Lee, J.H. Han, P.S. Kwon, S. Bhuniya, J.Y. Kim, and J.L. Sessler Hepatocyte-targeting single galactose-appended naphthalimide: a tool for intracellular thiol imaging in vivo J Am Chem Soc 134 2 2012 1316 1322
31. C.S. Lim, G. Masanta, H.J. Kim, J.H. Han, H.M. Kim, and B.R. Cho Ratiometric detection of mitochondrial thiols with a two-photon fluorescent probe J Am Chem Soc 133 29 2011 11132 11135
32. B. Tang, Y. Xing, P. Li, N. Zhang, F. Yu, and G. Yang A rhodamine-based fluorescent probe containing a Se-N bond for detecting thiols and its application in living cells J Am Chem Soc 129 38 2007 11666 11667 (Pubitemid 47479900)
33. K.S. Lee, T.K. Kim, J.H. Lee, H.J. Kim, and J.I. Hong Fluorescence turn-on probe for homocysteine and cysteine in water Chem Commun 46 2008 6173 6175
34. S. Lim, J.O. Escobedo, M. Lowry, X. Xu, and R. Strongin Selective fluorescence detection of cysteine and N-terminal cysteine peptide residues Chem Commun 46 31 2010 5707 5709
35. L. Yuan, W. Lin, and Y. Yang A ratiometric fluorescent probe for specific detection of cysteine over homocysteine and glutathione based on the drastic distinction in the kinetic profiles Chem Commun 47 22 2011 6275 6277
36. X. Liu, N. Xi, S. Liu, Y. Ma, H. Yang, and H. Li Highly selective phosphorescent nanoprobes for sensing and bioimaging of homocysteine and cysteine J Mater Chem 22 16 2012 7894
37. M. Hu, J. Fan, H. Li, K. Song, S. Wang, and G. Cheng Fluorescent chemodosimeter for Cys/Hcy with a large absorption shift and imaging in living cells Org Biomol Chem 9 4 2011 980 983
38. P. Wang, J. Liu, X. Lv, Y. Liu, Y. Zhao, and W. Guo A naphthalimide-based glyoxal hydrazone for selective fluorescence turn-on sensing of Cys and Hcy Org Lett 14 2 2012 520 523
39. X. Zhang, X. Ren, Q.H. Xu, K.P. Loh, and Z.K. Chen One- and two-photon turn-on fluorescent probe for cysteine and homocysteine with large emission shift Org Lett 11 6 2009 1257 1260
40. M. Zhang, M. Li, Q. Zhao, F. Li, D. Zhang, and J. Zhang Novel Y-type two-photon active fluorophore: synthesis and application in fluorescent sensor for cysteine and homocysteine Tetrahedron Lett 48 13 2007 2329 2333 (Pubitemid 46335807)
41. X.F. Guo, H. Wang, Y.H. Guo, and H.S. Zhang Selective spectrofluorimetric determination of glutathione in clinical and biological samples using 1,3,5,7-tetramethyl-8-phenyl-(2-maleimide)-difluoroboradiaza-s-indacene Anal Chim Acta 633 1 2009 71 75
42. S. Sreejith, K.P. Divya, and A. Ajayaghosh A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma Angew Chem Int Ed 47 41 2008 7883 7887
43. X. Yang, Y. Guo, and R.M. Strongin Conjugate addition/cyclization sequence enables selective and simultaneous fluorescence detection of cysteine and homocysteine Angew Chem Int Ed 50 45 2011 10690 10693
44. L. Yi, H. Li, L. Sun, L. Liu, C. Zhang, and Z. Xi A highly sensitive fluorescence probe for fast thiol-quantification assay of glutathione reductase Angew Chem Int Ed 48 22 2009 4034 4037
45. X. Chen, S.K. Ko, M.J. Kim, I. Shin, and J. Yoon A thiol-specific fluorescent probe and its application for bioimaging Chem Commun 46 16 2010 2751 2753
46. H.S. Jung, J.H. Han, Y. Habata, C. Kang, and J.S. Kim An iminocoumarin-Cu(II) ensemble-based chemodosimeter toward thiols Chem Commun 47 18 2011 5142 5144
47. H. Kwon, K. Lee, and H.J. Kim Coumarin-malonitrile conjugate as a fluorescence turn-on probe for biothiols and its cellular expression Chem Commun 47 6 2011 1773 1775
48. H. Wang, G. Zhou, H. Gai, and X. Chen A fluorescein-based probe with high selectivity to cysteine over homocysteine and glutathione Chem Commun 48 67 2012 8341 8343
49. H. Zhang, P. Wang, Y. Yang, and H. Sun A selective fluorescent probe for thiols based on alpha, beta-unsaturated acyl sulfonamide Chem Commun 48 86 2012 10672 10674
50. W. Lin, L. Yuan, Z. Cao, Y. Feng, and L. Long A sensitive and selective fluorescent thiol probe in water based on the conjugate 1,4-addition of thiols to alpha, beta-unsaturated ketones Chemistry 15 20 2009 5096 5103
51. Y. Liu, Y. Yu, J.W. Lam, Y. Hong, M. Faisal, and W.Z. Yuan Simple biosensor with high selectivity and sensitivity: thiol-specific biomolecular probing and intracellular imaging by AIE fluorogen on a TLC plate through a thiol-ene click mechanism Chemistry 16 28 2010 8433 8438
52. V. Hong, A.A. Kislukhin, and M.G. Finn Thiol-selective fluorogenic probes for labeling and release J Am Chem Soc 131 29 2009 9986 9994
53. T. Matsumoto, Y. Urano, T. Shoda, H. Kojima, and T. Nagano A thiol-Reactive fluorescence probe based on donor-excited photoinduced electron transfer: key role of ortho substitution Org Lett 9 17 2007 3375 3377
54. L. Zhou, Y. Lin, Z. Huang, J. Ren, and X. Qu Carbon nanodots as fluorescence probes for rapid, sensitive, and label-free detection of Hg2+ and biothiols in complex matrices Chem Commun 48 8 2012 1147 1149
55. Y. Fujikawa, Y. Urano, T. Komatsu, K. Hanaoka, H. Kojima, and T. Terai Design and synthesis of highly sensitive fluorogenic substrates for glutathione S-transferase and application for activity imaging in living cells J Am Chem Soc 130 44 2008 14533 14543
56. Z. Meng, Y.M. Xiao, L.F. You, Z.M. Wei, L.M. Yu, and G.Y. ong A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging J Am Chem Soc 129 2007 10322 10323
57. M. Zhang, M. Yu, F. Li, M. Zhu, M. Li, and Y. Gao A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging J Am Chem Soc 129 34 2007 10322 10323 (Pubitemid 47330235)
58. J. Ren, Z. Wu, Y. Zhou, Y. Li, and Z. Xu Colorimetric fluoride sensor based on 1,8-naphthalimide derivatives Dyes Pigm 91 3 2011 442 445