A highly selective fluorescent probe for detection of biological samples thiol and its application in living cells

Journal of Fluorescence

Volumn 20, Issue 6, 2010, Pages 1307-1313

  Zuo, Qing Ping ^a   Li, Bing ^a   Pei, Qi ^a   Li, Zuojun ^a   Liu, Shi Kun ^a  

^a CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

Fluorescence; Fluorescent probe; Sensing; Thiols

Indexed keywords

ANALYTES; BIOLOGICAL SAMPLES; BLOOD SAMPLES; FLUORESCENCE INTENSITIES; FLUORESCENCE QUANTUM YIELD; FLUORESCENT PROBES; HUMAN URINE; LIVING CELL; MOLECULAR PROBES; PHYSIOLOGICAL CONDITION; SENSING; THIOLS;

FLUORESCENCE SPECTROSCOPY; PROBES; QUANTUM YIELD;

FLUORESCENCE;

FLUORESCENT DYE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; FLUORESCENCE MICROSCOPY; HUMAN; PATHOLOGY; PH; QUANTUM THEORY; SQUAMOUS CELL CARCINOMA; SYNTHESIS; TONGUE TUMOR; ULTRAVIOLET SPECTROPHOTOMETRY;

CARCINOMA, SQUAMOUS CELL; FLUORESCENCE; FLUORESCENT DYES; HUMANS; HYDROGEN-ION CONCENTRATION; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; QUANTUM THEORY; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFHYDRYL COMPOUNDS; TONGUE NEOPLASMS;

EID: 78650784015     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-010-0673-6     Document Type: Article

References (42)

1. SY Zhang CN Ong HM Shen 2004 Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells Cancer Lett 208 143 153 10.1016/j.canlet.2003.11.028 1:CAS:528: DC%2BD2cXktVOmurY%3D 10.1016/j.canlet.2003.11.028 15142672 (Pubitemid 38624155)
2. H Wang WS Wang HS Zhang 2001 A spectrofluorimetric method for cysteine and glutathione using the fluorescence system of Zn(II)-8-hydroxyquinoline-5- sulphonic acid complex Spectrochim Acta Part A 57 2403 2407 10.1016/S1386- 1425(01)00429-2 1:STN:280:DC%2BD38%2FjvVWgsA%3D%3D 10.1016/S1386-1425(01)00429-2
3. R Kizek J Vacek L Trnkova F Jelen 2004 Cyclic voltammetric study of the redox system of glutathione using the disulfide bond reductant tris(2-carboxyethyl)phosphine Bioelectrochemistry 63 19 24 10.1016/j.bioelechem. 2003.12.001 1:CAS:528:DC%2BD2cXjsVWisr4%3D 10.1016/j.bioelechem.2003.12.001 15110242 (Pubitemid 38534189)
4. B Schulz JB J Lindenau J Seyfried J Dichgans 2000 Glutathione oxidative stress and neurodegeneration Eur J Biochem 267 4904 4911 10.1046/j.1432-1327. 2000.01595.x 10.1046/j.1432-1327.2000.01595.x 10931172 (Pubitemid 30641286)
5. RO Ball G Courtney-Martin PB Pencharz 2006 The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans J Nutr 136 1682S 1693S 1:CAS:528:DC%2BD28Xlt1Wnu7Y%3D 16702340
6. S Shahrokhian 2001 Lead phthalocyanine as a selective carrier for preparation of a cysteine- selective electrode Anal Chem 73 5972 5978 10.1021/ac010541m 1:CAS:528:DC%2BD3MXotV2nur0%3D 10.1021/ac010541m 11791568 (Pubitemid 34042214)
7. MT Heafield S Fearn GB Steventon RH Waring AC Williams SG Sturman 1990 Plasma cysteine and sulphate levels in patients with motor neurone, Parkinson's and Alzheimer's disease Neurosci Lett 110 216 220 10.1016/0304-3940(90)90814-P 1:STN:280:DyaK3c3itFagtQ%3D%3D 10.1016/0304-3940(90)90814-P 2325885
8. C Sofia B Chadefaux M Coude O Oaillard E Kamoun 1990 Concentrations of total homocysteine in plasma in chronic renal failure Clin Chem 36 2137 2138
9. O Nygard JE Nordrehaug H Refsum PM Ueland M Farstad E Vollset 1997 Plasma homocysteine levels and mortality in patients with coronary artery disease N Engl J Med 337 230 236 1:STN:280:DyaK2szlslantg%3D%3D 10.1056/ NEJM199707243370403 9227928 (Pubitemid 27310438)
10. DW Jacobsen 1998 Homocysteine and vitamins in cardiovascular disease Clin Chem 44 1833 1843 1:CAS:528:DyaK1cXlsVajt7Y%3D 9702993
11. S Seshadri A Beiser J Selhub PF Jacques IH Rosenberg RB D'Agostino PW Wilson PA Wolf 2002 Plasma homocysteine as a risk factor for dementia and Alzheimer's disease N Engl J Med 346 476 483 10.1016/S1062-1458(02)00690-6 1:CAS:528:DC%2BD38XhtFCktrw%3D 10.1056/NEJMoa011613 11844848 (Pubitemid 34441738)
12. C Komuro K Ono Y Shibamoto T Nishidai M Takahashi M Abe 1985 Rapid and simple method for quantitative determination of non-protein sulphydryls in mouse liver by reversed-phase high-performance liquid chromatography J Chromatogr 338 209 212 1:CAS:528:DyaL2MXht1yitrs%3D 10.1016/0378-4347(85)80087-6 4019645
13. W Chen Y Zhao T Seefeldt X Guan 2008 Determination of thiols and disulfides via HPLC quantification of 5-thio-2-nitrobenzoic acid J Pharm Biomed Anal 48 1375 1380 10.1016/j.jpba.2008.08.033 10.1016/j.jpba.2008.08.033 18926658
14. T Inoue JR Kirchhoff 2000 Electrochemical detection of thiols with a coenzyme pyrroloquinoline quinone modified electrode Anal Chem 72 5755 5760 10.1021/ac000716c 1:CAS:528:DC%2BD3cXnsFymurg%3D 10.1021/ac000716c 11128932 (Pubitemid 32002326)
15. A Zinellu S Sotgia B Scanu MF Usai AG Fois V Spada A Deledda L Deiana P Pirina C Carru 2009 Simultaneous detection of N-acetyl-l-cysteine and physiological low molecular mass thiols in plasma by capillary electrophoresis Amino Acids 37 395 400 10.1007/s00726-008-0167-x 1:CAS:528:DC%2BD1MXotVKisrk%3D 10.1007/s00726-008-0167-x 18695935
16. K Amarnath V Amarnath K Amarnath HL Valentine WM Valentine 2003 A specific HPLC-UV method for the determination of cysteine and related aminothiols in biological samples Talanta 60 1229 1238 10.1016/S0039-9140(03) 00232-7 1:CAS:528:DC%2BD3sXmsVOrsro%3D 10.1016/S0039-9140(03)00232-7 18969150
17. M Wen H Liu F Zhang Y Zhu D Liu Y Tian Q Wu 2009 Amorphous FeNiPt nanoparticles with tunable length for electrocatalysis and electrochemical determination of thiols Chem Commun (Camb). 30 4530 4532 10.1039/b907379e 10.1039/b907379e
18. L Duan Y Xu X Qian F Wang J Liu T Cheng 2008 Highly selective fluorescent chemosensor with red shift for cysteine in buffer solution and its bioimage: symmetrical naphthalimide aldehyde Tetrahedron Lett 49 6624 6627 10.1016/j.tetlet.2008.09.021 1:CAS:528:DC%2BD1cXht1CqsbjI 10.1016/j.tetlet.2008. 09.021
19. A Shibata K Furukawa H Abe S Tsuneda Y Ito 2008 Rhodamine-based fluorogenic probe for imaging biological thiol Bioorg Med Chem Lett 18 2246 2249 10.1016/j.bmcl.2008.03.014 1:CAS:528:DC%2BD1cXjvFyksb4%3D 10.1016/j.bmcl.2008. 03.014 18358719 (Pubitemid 351442915)
20. T Matsumoto Y Urano T Shoda H Kojima T Nagano 2007 A thiol-reactive fluorescence probe based on donor-excited photoinduced electron transfer: key role of ortho substitution Org Lett 9 3375 3377 10.1021/ol071352e 1:CAS:528:DC%2BD2sXotVKhtLs%3D 10.1021/ol071352e 17645349
21. AM Piggott P Karuso 2007 Fluorometric assay for the determination of glutathione reductase activity Anal Chem 79 8769 8773 10.1021/ac071518p 1:CAS:528:DC%2BD2sXhtFegsrbN 10.1021/ac071518p 17924649 (Pubitemid 350171391)
22. J Bouffard Y Kim TM Swager R Weissleder SA Hilderbrand 2008 A highly selective fluorescent probe for thiol bioimaging Org Lett 10 37 40 : 10.1021/ol702539v 1:CAS:528:DC%2BD2sXhtl2itLjL 10.1021/ol702539v 18062694
23. ST Huanga KN Ting KL Wang 2008 Development of a long-wavelength fluorescent probe based on quinine-methide-type reaction to detect physiologically significant thiols Anal Chim Acta 620 120 126 10.1016/j.aca.2008.05.006 10.1016/j.aca.2008.05.006
24. Fu YY, Li HX, Hu WP, Zhu DB (2005) Fluorescence probes for thiol-containing amino acids and peptides in aqueous solution. Chem Commun (Camb) 3189-3191. doi: 10.1039/b503772g (Pubitemid 41002391)
25. H Maeda H Matsuno M Ushida K Katayama K Saeki N Itoh 2005 2, 4-dinitrobenzenesulfonyl fluoresceins as fluorescent alternatives to Ellman's reagent in thiol-quantification enzyme assays Angew Chem Int Ed 44 2922 2925 10.1002/ange.200500114 1:CAS:528:DC%2BD2MXksVKlsb8%3D 10.1002/anie.200500114
26. M Zhang M Li Q Zhao FY Li DQ Zhang JP Zhang T Yi CH Huang 2007 Novel Y-type two-photon active fluorophore: synthesis and application in fluorescent sensor for cysteine and homocysteine Tetrahedron Lett 48 2329 2333 10.1016/j.tetlet.2007.01.158 1:CAS:528:DC%2BD2sXitlOkurg%3D 10.1016/j.tetlet. 2007.01.158 (Pubitemid 46335807)
27. CF Chow BKW Chiu MHW Lam WY Wong 2003 A trinuclear heterobimetallic Ru(II)/Pt(II) complex as a chemodosimeter selective for sulfhydryl-containing amino acids and peptides J Am Chem Soc 125 7802 7803 10.1021/ja034891x 1:CAS:528:DC%2BD3sXltVGgsL0%3D 10.1021/ja034891x 12822989 (Pubitemid 36782148)
28. Tanaka F, Mase N, Barbas CF (2004) Determination of cysteine concentration by fluorescence increase: reaction of cysteine with a fluorogenic aldehyde. Chem Commun (Camb) 1762-1763. doi: 10.1039/b405642f
29. L Wang XF Yang M Zhao 2009 A 4-methylumbelliferone-based fluorescent probe for the sensitive detection of captopril J Fluoresc 19 593 599 10.1007/s10895-008-0449-4 1:CAS:528:DC%2BD1MXosVGis70%3D 10.1007/s10895-008- 0449-4 19050997
30. S Sreejith KP Divya A Ajayaghosh 2008 A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma Angew Chem Int Ed 47 7883 7887 10.1002/ange.200803194 1:CAS:528:DC%2BD1cXht1OhsrfJ 10.1002/anie.200803194
31. W Lin L Yuan Z Cao Y Feng L Long 2009 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 15 5096 5103 10.1002/chem.200802751 1:CAS:528:DC%2BD1MXls12ksb4%3D 10.1002/chem.200802751
32. Burford N, Eelman MD, Mahony DE, Morash M (2003) Definitive identification of cysteine and glutathione complexes of bismuth by mass spectrometry: assessing the biochemical fate of bismuth pharmaceutical agents. Chem Commun (Camb) 146-147. doi: 10.1039/b210570e (Pubitemid 36051253)
33. M Rafii R Elango G Courtney-Martin JD House L Fisher PB Pencharz 2007 High-throughput and simultaneous measurement of homocysteine and cysteine in human plasma and urine by liquid chromatography-electro spray tandem mass spectrometry Anal Biochem 371 71 81 10.1016/j.ab.2007.07.026 1:CAS:528:DC%2BD2sXhtFGrtLnF 10.1016/j.ab.2007.07.026 17727809 (Pubitemid 47538484)
34. Y Zeng G Zhang D Zhang 2008 A selective colorimetric chemosensor for thiols based on intramolecular charge transfer mechanism Anal Chim Acta 627 254 257 10.1016/j.aca.2008.08.028 1:CAS:528:DC%2BD1cXhtFCitL%2FI 10.1016/j.aca.2008.08.028 18809081
35. Y Guo A Shao J Xu Y Shi S Jiang 2004 A specific colorimetric cysteine sensing probe based on dipyrromethane-TCNQ assembly Tetrahedron Lett 45 6477 6480 10.1016/j.tetlet.2004.06.109 1:CAS:528:DC%2BD2cXmt1Kjtbk%3D 10.1016/j.tetlet.2004.06.109 (Pubitemid 39091071)
36. X Zhang C Li X Cheng X Wang B Zhang 2008 A near-infrared croconium dye-based colorimetric chemodosimeter for biological thiols and cyanide anion Sens Acuators B 129 152 157 10.1016/j.snb.2007.07.094 10.1016/j.snb.2007.07.094
37. FJ Huo YQ Sun J Su JB Chao HJ Zhi CX Yin 2009 Colorimetric detection of thiols using a chromene molecule Org Lett 11 4918 4921 10.1021/ol901951h 1:CAS:528:DC%2BD1MXhtF2ltb7J 10.1021/ol901951h 19788282
38. Lakowicz JR (2002) Topics in fluorescence spectroscopy. Kluwer Academic Publishers, New York
39. L Yi H Li L Sun L Liu C Zhang Z Xi 2009 A highly sensitive fluorescence probe for fast thiol-quantification assay of glutathione reductase Angew Chem Int Ed Engl 48 4034 4037 10.1002/anie.200805693 1:CAS:528:DC%2BD1MXmtVKms70%3D 10.1002/anie.200805693 19388016
40. T Inoue JR Kirchhoff 2002 Determination of thiols by capillary electrophoresis with amperometric detection at a coenzyme pyrroloquinoline quinone modified electrode Anal Chem 74 1349 1354 10.1021/ac0108515 1:CAS:528:DC%2BD38XhtFKnsLw%3D 10.1021/ac0108515 11922303 (Pubitemid 34233326)
41. MP Brigham WH Stein S Moore 1960 The concentrations of cysteine and cystine in human blood plasma J Clin Invest 39 1633 1638 10.1172/JCI104186 1:CAS:528:DyaF3MXitlyntQ%3D%3D 10.1172/JCI104186 16695834
42. M Zhang M Yu F Li M Zhu M Li Y Gao L Li Z Liu J Zhang D Zhang T Yi C Huang 2007 A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging J Am Chem Soc 129 10322 10323 10.1021/ja073140i 1:CAS:528:DC%2BD2sXosVWitbY%3D 10.1021/ja073140i 17672463 (Pubitemid 47330235)