A fluorescent probe for biothiols based on the conjugate addition of thiols to α,β-unsaturated ester

Luminescence

Volumn 26, Issue 6, 2011, Pages 486-493

  Du, Jun ^a   Yang, Zhe ^a   Qi, Haiping ^a   Yang, Xiao Feng ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

benzimidazole; biothiols; fluorescent probe; Michael addition

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; CARBON; CHLORINE COMPOUNDS; FLUORESCENCE SPECTROSCOPY; FLUOROPHORES;

ACRYLOYL CHLORIDE; BENZIMIDAZOLES; BIOTHIOLS; CONJUGATE ADDITION; FLUORESCENT PROBES; FLUOROGENIC PROBES; MICHAEL ADDITION REACTIONS; MICHAEL ADDITIONS; SYNTHESISED; Β-UNSATURATED ESTERS;

PROBES;

EID: 83455205947     PISSN: 15227235     EISSN: 15227243     Source Type: Journal    
DOI: 10.1002/bio.1257     Document Type: Article

References (39)

1. Cecchi C, Latorraca S, Sorbi S, Iantomasi T, Favilli F, Vincenzini MT, Liguri G,. Gluthatione level is altered in lymphoblasts from patients with familial Alzheimer's disease. Neurosci Lett 1999; 275: 152-4. (Pubitemid 29502559)
2. Staal FJ, Ela TS, Roederer M, Anderson MT, Herzenberg LA,. Glutathione deficiency and human immunodeficiency virus infection. Lancet 1992; 339: 909-12.
3. White AC, Thannickal VJ, Fanburg BL,. Glutathione deficiency in human disease. J Nutr Biochem 1994; 5: 218-26. (Pubitemid 24156610)
4. 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 Edn 2009; 48: 4034-7.
5. Lin W, Yuan L, Cao Z, Feng Y, Long L,. A sensitive and selective fluorescent thiol probe in water based on the conjugate 1,4-addition of thiols to α,β-unsaturated ketones. Chem Eur J 2009; 15: 5096-103.
6. Matsumoto T, Urano Y, Shoda T, Kojima H, Nagano T,. A thiol-reactive fluorescence probe based on donor-excited photoinduced electron transfer: key role of ortho substitution. Org Lett 9: 3375-7.
7. Guo XF, Wang H, Guo YH, Zhang HS,. 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 2009; 633: 71-5.
8. Chen XQ, Ko SK, Kim MJ, Shin I, Yoon J,. A thiol-specific fluorescent probe and its application for bioimaging. Chem Commun 2010; 46: 2751-3.
9. Sreejith S, Divya KP, Ajayaghosh A,. A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma. Angew Chem Int Ed 2008; 47: 7883-7.
10. Li HL, Fan JL, Wang JY, Tian MZ, Du JJ, Sun SG, Sun PP, Peng XJ,. A fluorescent chemodosimeter specific for cysteine: effective discrimination of cysteine from homocysteine. Chem Commun 2009; 5904-6.
11. Wang WH, Rusin O, Xu XY, Kim KK, Escobedo JO, Fakayode SO, Fletcher KA, Lowry M, Schowalter CM, Lawrence CM, Fronczek FR, Warner IM, Strongin RM,. Detection of homocysteine and cysteine. J Am Chem Soc 2005; 127: 15949-58. (Pubitemid 41643305)
12. Lee KS, Kim TK, Lee JH, Kim HJ, Hong JI,. Fluorescence turn-on probe for homocysteine and cysteine in water. Chem Commun 2008; 6173-5.
13. Tanaka F, Mase N, Barbas III CF., Determination of cysteine concentration by fluorescence increase: reaction of cysteine with a fluorogenic aldehyde. Chem Commun 2004; 1762-3. (Pubitemid 39127871)
14. Li HL, Fan JL, Wang Y, Tian MZ, Du JJ, Sun SG, Sun PP, Peng XJ,. A fluorescent chemodosimeter specific for cysteine: effective discrimination of cysteine from homocysteine. Chem Commun 2009; 5904-6.
15. Duan LP, Xu YF, Qian XH, Wang F, Liu JW, Cheng TY,. Highly selective fluorescent chemosensor with red shift for cysteine in buffer solution and its bioimage: symmetrical naphthalimide aldehyde. Tetrahedron Lett 2008; 49: 6624-7.
16. Kim TK, Lee DN, Kim HJ,. Highly selective fluorescent sensor for homocysteine and cysteine. Tetrahedron Lett 2008; 49: 4879-81.
17. Zhang M, Li MY, Zhao Q, Li FY, Zhang DQ, Zhang JP, Yi T, Huang CH., Novel Y-type two-photon active fluorophore: synthesisand application in fluorescent sensor for cysteine and homocysteine. Tetrahedron Lett 2007; 48: 2329-33. (Pubitemid 46335807)
18. Zhang XJ, Ren XS, Xu QH, Loh KP, Chen ZK,. One- and two-photon turn-on fluorescent probe for cysteine and homocysteine with large emission shift. Org Lett 2009; 11: 1257-60.
19. Maeda H, Matsuno H, Ushida M, Katayama K, Saeki K, Itoh N,. 2,4-Dinitrobenzenesulfonyl fluoresceins as fluorescent alternatives to Ellman's reagent in thiol-quantification enzyme assays. Angew Chem Int Edn 2005; 44: 2922-5. (Pubitemid 40689674)
20. Wang SP, Deng WJ, Sun D, Yan M, Zheng H, Xu JG,. A colorimetric and fluorescent merocyanine-based probe for biological thiols. Org Biomol Chem 2009; 7: 4017-20.
21. Bouffard J, Kim Y, Swager TM, Weissleder R, Hilderbrand SA,. A highly selective fluorescent probe for thiol bioimaging. Org Lett 2008; 10: 37-40.
22. Jiang W, Fu QQ, Fan HY, Ho J, Wang W,. A highly selective fluorescent probe for thiophenols. Angew Chem Int Edn 2007; 46: 8445-8. (Pubitemid 350114957)
23. Shibata A, Furukawa K, Abe H, Tsuneda S, Ito Y,. Rhodamine-based fluorogenic probe for imaging biological thiol. Bioorg Med Chem Lett 2008; 18: 2246-9. (Pubitemid 351442915)
24. Tang B, Yin LL, Wang X, Chen ZZ, Tong LL, Xu KH,. A fast-response highly sensitive and specific organoselenium fluorescent probe for thiols and its application in bioimaging. Chem Commun 2009; 5293-5.
25. Tang B, Xing YL, Li P, Zhang N, Yu FB, Yang GW,. A rhodamine-based fluorescent probe containing a Se-N bond for detecting thiols and its application in living cells. J Am Chem Soc 2007; 129: 11666-7. (Pubitemid 47479900)
26. Yang XF, Su Z, Liu CH, Qi HP, Zhao ML,. A thiol-selective fluorogenic probe based on the cleavage of 4-methylumbelliferyl-2′,4′,6′- trinitropheyl ether. Anal Bioanal Chem 2010; 396: 2667-74.
27. Hong V, Kislukhin AA, Finn MG,. Thiol-selective fluorogenic probes for labeling and release. J Am Chem Soc 2009; 131: 9986-94.
28. 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 Chem Soc 2007; 129: 10322-3. (Pubitemid 47330235)
29. Huang ST, Ting KN, Wang KL,. Development of a long-wavelength fluorescent probe based on quinone-methide-type reaction to detect physiologically significant thiols. Anal Chim Acta 2008; 620: 120-6.
30. Lee JH, Lim CS, Tian YS, Han JH, Cho BR,. A two-photon fluorescent probe for thiols in live cells and tissues. J Am Chem Soc 2010; 132: 1216-7.
31. Pires MM, Chmielewski J,. Fluorescence imaging of cellular glutathione using a latent rhodamine. Org lett 2008; 10: 837-40.
32. Dubernet M, Caubert V, Guillard J, Viaud-Massuard M., Synthesis of substituted bis(heteroaryl)maleimides. Tetrahedron 2005; 61: 4585-93. (Pubitemid 40523664)
33. Kalia J, Raines RT,. Catalysis of imido group hydrolysis in a maleimide conjugate. Bioorg Med Chem Lett 2007; 17: 6286-9. (Pubitemid 47552813)
34. Khatik GL, Kumar R, Chakraborti AK,. Catalyst-free conjugated addition of thiols to α, β-unsaturated carbonyl compounds in water. Org Lett 2006; 8: 2433-6. (Pubitemid 43998275)
35. Tavman A,. Synthesis, spectral characterisation of 2-(5-methyl-1H- benzimidazol-2-yl)-4-bromo/nitro-phenols and their complexes with zinc(II) ion, and solvent effect on complexation. Spectrochim Acta A 2006; 63: 343-8. (Pubitemid 43131478)
36. Fan NT, editors. Organic synthesis dictionaries. Beijing: Beijing University of Technology Press, 1992.
37. Whitesides GM, Lilburn JE, Szajewski RP, Rates of thiol-disulfide interchange reactions between monoand dithiols and ellman's reagent. J Org Chem 1977; 42: 332-8.
38. Prieto FR, Rodriguez MCR, Gonzalez MM, Fernandez MAR, Ground- and excited-state tautomerism in 2-(3′-hydroxy-2′-pyridyl) benzimidazole. J Phys Chem 1994; 98: 8666-72.
39. Inoue T, Kirchhoff JR,. Determination of thiols by capillary electrophoresis with amperometric detection at a coenzyme pyrroloquinoline quinone modified electrode. Anal Chem 2002; 74: 1349-54. (Pubitemid 34233326)