Suppression of thiol exchange reaction in the determination of reduced-form thiols by high-performance liquid chromatography with fluorescence detection after derivatization with fluorogenic benzofurazan reagent, 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate and 4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole

Biomedical Chromatography

Volumn 20, Issue 6-7, 2006, Pages 656-661

  Santa, Tomofumi ^a   Aoyama, Chiaki ^a   Fukushima, Takeshi ^b   Imai, Kazuhiro ^c   Funatsu, Takashi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

^c MUSASHINO UNIVERSITY   (Japan)

Author keywords

4 aminosulfonyl 7 fluoro 2,1,3 benzoxadiazole (ABD F); 7 fluoro 2,1,3 benzoxadiazole 4 sulfonate (SBD F); Benzofurazan; Cysteine; Glutathione; Homocysteine; Thiol exchange

Indexed keywords

AMINO ACIDS; BROMINE COMPOUNDS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; TEMPERATURE;

4-AMINOSULFONYL-7-FLUORO-2,1,3-BENZOXADIAZOLE (ABD-F); 7-FLUORO-2,1,3-BENZOXADIAZOLE-4-SULPHONATE (SBD-F); BENZOFURAZAN; CYSTEINE; DERIVATIZATIONS; GLUTHATHIONE; HOMOCYSTEINES; SULPHONATES; THIOL EXCHANGE; THIOL EXCHANGE REACTIONS;

PEPTIDES;

4 AMINOSULFONYL 7 FLUORO 2,1,3 BENZOXADIAZOLE; 7 FLUORO 2,1,3 BENZOXADIAZOLE 4 SULFONATE; BENZOFURAZAN DERIVATIVE; BORIC ACID; BROMOBIMANE; BUFFER; CYSTEINE; GLUTATHIONE; HOMOCYSTEINE; PHTHALALDEHYDE; REAGENT; THIOL; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DERIVATIZATION; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LOW TEMPERATURE; OXIDATION REDUCTION REACTION; PH; SAMPLE;

EID: 33745884368     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.683     Document Type: Article

References (29)

1. Abukhalaf IK, Silvestrov NA, Menter JM, von Deutsch DA, Bayorh MA, Socci RR, Ganafa AA. High performance liquid chromatographic assay for quantitation of total glutathione in plasma. Journal of Pharmaceutical and Biomedical Analysis 2002: 28: 637-643.
2. Camera E and Picardo M. Analytical methods to investigate glutathione and related compounds in biological and pathological process. Journal of Chromatography B 2002; 781: 181-206.
3. Daskalakis I, Lucock MD, Anderson A, Wild J, Schorah CJ and Levene MI. Determination of plasma total homocysteine and cysteine using HPLC with fluorescence detection and an ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F) derivatization protocol optimization reagent concentration, temperature, and matrix pH. Biomedical Chromatography 1996; 10: 205-212.
4. Ducros V, Demuth K, Sauvant M-R, Quillard M, Causse E, Candito M, Read M-H, Drai J, Garcia I, Gerhardt M-F. Methods for homocysteine analysis and biological relevance of the results. Journal of Chromatography B 2002; 781: 207-226.
5. Ercal N, Yang P and Aykin N. Determination of biological thiols by high-performance liquid chromatography following derivatization by ThioGlo maleimide. Journal of Chromatography B 2001; 753: 287-292.
6. Giustarini D, Dalle-Donne A, Colombo R, Milzani A and Rossi R. Interference of plasmatic reduced glutathione and homolysis on glutathione disulfide levels in human blood. Free Radical Research 2004; 38: 1101-1106.
7. Imai K, Uzu S and Toyo'oka T. Fluorogenic reagents, having benzofurazan structure, in liquid chromatography. Journal of Pharmaceutical and Biomedical Analysis 1989: 7: 1395-1403.
8. Imai K, Uzu S, Kanda S and Baeyens WRG. Availability of fluorogenic reagents having a benzofurazan structure in the biosciences. Analytica Chimica Acta 1994: 290: 3-20.
9. Ivanov AR, Nazimov IV and Baratova LA. 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. Journal of Chromatography A 2000; 870: 433-442.
10. Ivanov AR, Nazamov IV, Baratova L, Lobazov AP and Popkovich GB. Determination of biologically active low molecular-mass thiols in human blood. Journal of Chromatography A 2001; 913: 315-318.
11. Komatsu H and Obata F. An optimized method for determination of intracellular glutathione in mouse macrophage cultures by fluorimetric high-performance liquid chromatography. Biomedical Chromatography 2003; 17: 345-350.
12. Luo JL, Hammarqvist F, Cotgreave IA, Lind C, Anderson K and Wernerman J. Determination of intracellular glutathione in human skeletal muscle by reversed-phase high-performance liquid chromatography. Journal of Chromatography B 1995; 670: 29-36.
13. Mansoor MA, Svardal AM and Ueland PM. Determination of the in vivo redox status of cysteine, cysteinylglycine, homocysteine and glutathione in human plasma. Analytical Biochemistry 1992; 200: 218-229.
14. Molnar-Perl I. Derivatization and chromatographic behavior of the o-phthaldialdehyde amino acid derivatives obtained with various SH-group-containing additives. Journal of Chromatography A 2001; 913: 283-302.
15. Nekrassova O, Lawrence NS, Copton RG. Analytical determination of homocysteine: a review. Talanta 2003; 60: 1085-1095.
16. Oe T, Ohyagi T and Naganuma A. Determination of γ-glutamylglutathione and other low-molecular-mass biological thiol compounds by isocratic high-performance liquid chromatography with fluorimetric detection. Journal of Chromatography 1998; 708: 285-289.
17. Ozkan Y, Ozkan E and Simsek B. Plasma total homocysteine and cysteine levels as cardiovascular risk factors in coronary heart disease. Internal Journal of Cardiology 2002; 82: 269-277.
18. Parmentier C, Leroy P, Wellman M and Nicolas A. Determination of cellular thiols and glutathione-related enzymes activities: versatility of high-performance liquid chromatography-spectrofluorometric detection. Journal of Chromatography B 1998; 719: 37-46.
19. Pastore A, Federici G, Bertini E and Piemonte F. Analysis of glutathione: implication in redox and detoxication. Clinica Chimica Acta 2003; 333: 19-39.
20. Pfeiffer CM, Huff D and Gunter EW. Rapid and accurate HPLC assay for plasma total homocysteine and cysteine in a clinical laboratory setting. Clinical Chemistry 1999; 45: 290-292.
21. Rizzo V, Montalbetti L, Valli M, Bostoni T, Scoglio E and Moratti R. Study of factors affecting the determination of total plasma 7-fluorobenzo-2-oxa-1,3-diazole-4-sulfonate (SBD)-thiol derivatives by liquid chromatography. Journal of Chromatography B 1998; 706: 209-215.
22. Rossi R, Milzani A, Dalle-Donne I, Giustarini D, Lusini L, Colombo R and Di Simplicio P. Blood glutathione disulfide: in vivo factor or in vitro artifact? Clinical Chemistry 2002; 48: 742-753.
23. Tang D, Wen LS, Santschi PH. Analysis of biogenic thiols in natural water samples by high-performance liquid chromatographic separation and fluorescence detection with ammonium 7-fluorobenzo-2-oxa-1,3-diazole-4-sulfonate (SBD-F). Analytica Chimica Acta 2000; 408: 299-307.
24. Toyo'oka T and Imai K. High-performance liquid chromatography and fluorometric detection of biologically important thiols, derivatized with ammonium 7-fluorobenzo-2-oxa-1,3-diazole-4-sulfonate. Journal of Chromatography 1983; 282: 495-500.
25. Toyo'oka T, Uchiyama S, Saito Y and Imai K. Simultaneous determination of thiols and disulfides by high-performance liquid chromatography with fluorescence detection. Analytica Chimica Acta 1988; 205: 29-41.
26. Toyo'oka T, Furukawa F, Suzuki T, Saito Y, Takahashi M, Uzu S and Imai K. Determination of thiols and disulfides in normal rat tissues and hamster pancreas treated with N-nitrosobis(2-oxopropyl)amine using 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole and ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate. Biomedical Chromatography 1989; 3: 166-172.
27. Uchiyama S, Santa T, Okiyama N, Fukushima T and Imai K. Fluorogenic and fluorescent labeling reagents with a benzofurazan skelton. Biomedical Chromatography 2001; 15: 295-318.
28. Wang H, Liang S-C, Zhang Z-M and Zhang H-S. 3-Iodoacetylaminobenzanthrone as a fluorescent derivatizing reagent for thiols in high-performance liquid chromatography. Analytica Chimica Acta 2004; 512: 281-286.
29. Yoshida Y, Ohiwa Y, shimamura M, Izumi T, Yoshida S, Takahashi K, Miyairi S, Makimura M and Naganuma A. Optimum conditions for derivatization of glutathione, cysteine and cysteinylglycine in human plasma with ammonium 7-fluorobenzo-2-oxa-1,3-diazole-4-sulfonate for accurate quantification by high-performance liquid chromatography. Journal of Health Science 2003; 49: 527-530.