Development of a 6-hydroxychroman-based derivatization reagent: Application to the analysis of 5-hydroxytryptamine and catecholamines by using high-performance liquid chromatography with electrochemical detection

Biomedical Chromatography

Volumn 22, Issue 8, 2008, Pages 888-899

  Sasaki, Tsukasa ^a   Fukushima, Takeshi ^a   Ohishi, Madoka ^a   Toyo'oka, Toshimasa ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

5 hydroxytryptamine; Catecholamines; Chroman; Derivatization reagent; Electrochemical detection; High performance liquid chromatography; Rat urine

Indexed keywords

AMINES; BODY FLUIDS; CARBOXYLATION; CHEMICAL DETECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORMONES; NEUROPHYSIOLOGY; RATS; SIGNAL TO NOISE RATIO;

5-HYDROXYTRYPTAMINE; CATECHOLAMINE; CHROMAN; DERIVATIZATION REAGENT; DOPAMINE; ELECTROCHEMICAL DETECTION; ELECTROCHEMICAL RESPONSE; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; NORMETANEPHRINE; RAT URINE;

METABOLITES;

2,5 DIOXOPYRROLIDIN 1 YL 2,5,7,8 TETRAMETHYL 6 (TETRAHYDRO 2H PYRAN 2 YLOXY)CHROMAN 2 CARBOXYLIC ACID; 3 O METHYLDOPAMINE; 3,4 DIHYDROXYPHENYLACETIC ACID; 5 HYDROXYINDOLEACETIC ACID; 6 HYDROXY 2,2,5,7,8 PENTAMETHYLCHROMAN; ADRENALIN; CATECHOLAMINE; DOPAMINE; HOMOVANILLIC ACID; METADRENALIN; SEROTONIN;

ACCURACY; ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; COULOMETRY; DERIVATIZATION; ELECTROCHEMICAL ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; RAT; SIGNAL NOISE RATIO; STRUCTURE ANALYSIS; URINALYSIS;

RATTUS;

EID: 50049123936     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1007     Document Type: Article

References (36)

1. Adamczyk M, Fishpaugh JR and Mattingly PG. Preparation and use of N-hydroxysuccinimidyl active ester resins. Tetrahedron Letters 1999; 40: 463.
2. Forster CD and Macdonald IA. The assay of the catecholamine content of small volumes of human plasma. Biomedical Chromatography 1999; 13: 209.
3. Jones BJ and Blackburn TP. The medical benefit of 5-HT research. Pharmacology Biochemistry and Behavior 2002; 71: 555.
4. Kantoci D, Wechter WJ, Murray Jr. ED, Dewind SA, Borchardt D and Khan SI. Endogenous natriuretic factors 6: the stereochemistry of a natriuretic γ-tocopherol metabolite LLU-α The Journal of Pharmacology and Experimental Therapeutics 1997; 282: 648.
5. Kiyose C, Saito H, Kaneko K, Hamamura K, Tomioka M, Ueda T and Igarashi O. α-Tocopherol affects the urinary and biliary excretion of 2,7,8-trimethyl-2(2′-carboxyethyl)-6-hydroxychroman, γ-tocopherol metabolite, in rats. Lipids 2001; 36: 467.
6. Liu YL, Cheng ATA, Chen HR and Hsu YPP. Simultaneous HPLC of twelve monoamines and metabolites shows neuroblastoma cell line releases HVA and HIAA. Biomedical Chromatography 2000; 14: 544.
7. Lodge JK, Traber MG, Elsner A and Brigelius-Flohe R. A rapid method for the extraction and determination of vitamin E metabolites in human urine. Journal of Lipid Research 2000; 41: 148.
8. Lou R, Alstine MV, Sun X and Wentland W. Preparation of N-hydroxysuccinimido esters via palladium-catalyzed carbonylation of aryl triflates and halides. Tetrahedron Letters 2003; 44: 2477.
9. Marzanna PC and Anna W. Spectrofluorimetric determination of hydrogen peroxide scavenging activity. Analytica Chimica Acta 2002; 452: 177.
10. Minami T, Matsumoto Y, Nakamura S, Koyanagi S and Yamaguchi M. 3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes. Journal of Organic Chemistry 1992; 57: 167.
11. Miyashita M, Yoshikoshi A and Grieco PA. Pyridinium p-toluene-sulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcohols. Journal of Organic Chemistry 1977; 42: 3772.
12. Nemeroff CB. The burden of severe depression: a review of diagnostic challenges and treatment alternatives. Journal of Psychiatric Research 2007; 41: 189.
13. 1. Simplified and improved polymeric perfluorinated resin sulfonic acid (Nafion-H) catalyzed protection-deprotection reactions. Synthesis 1983; 11: 892.
14. Pallis EG, Spyraki C and Thermos K. Chronic antidepressant treatment modulates the release of somatostatin in the rat nucleus accumbens. Neuroscience Letters 2006; 395: 76.
15. Parrot S, Lambas-Senas L, Sentenac S, Denoroy L and Renaud B. Highly sensitive assay for the measurement of serotonin in micro-dialysates using capillary high-performance liquid chromatography with electrochemical detection. Journal of Chromatography B 2007; 850: 303.
16. Passarinha LA, Bonifacio MJ and Queiroz JA. The effect of temperature on the analysis of metanephrine for catechol-O-methyltransferase activity assay by HPLC with electrochemical detection. Biomedical Chromatography 2006; 20: 937.
17. Pinhey T and Xuan PT. The thermal ortho-substitution of phenols by vinyl ethers. Australian Journal of Chemistry 1988; 41: 69.
18. Rose MJ, Lunte SM, Carlson RG and Stobaugh JF. Hydroquinone-based derivatization reagents for the quantitation of amines using electrochemical detection. Analytical Chemistry 1999; 71: 2221.
19. Rose MJ, Lunte SM, Carlson RG and Stobaugh JF. Amino acid and peptide analysis using derivatization with p-nitrophenol-2,5-dihydroxyphenylacetate bis-tetrahydropyranyl ether and capillary electrophoresis with electrochemical detection. Journal of Pharmaceutical and Biomedical Analysis 2003; 30: 1851.
20. Sastre E, Nicolay A, Bruguerolle B and Portugal H. Method for simultaneous measurement of norepinephrine, 3-methoxy-4-hydroxyphenylglycol and 3,4-dihydroxyphenylglycol by liquid chromatography with electrochemical detection: application in rat cerebral cortex and plasma after lithium chloride treatment. Journal of Chromatography B 2004; 801: 205.
21. Srikrishna A, Sattigeri JA, Viswajanani R and Yelamaggad CV. Simple and regioselective reductive cleavage of tetrahydropyranyl ethers to alcohols. Journal of Organic Chemistry 1995; 60: 2260.
22. Stahl W, Graf P, Brigelius-Flohe R, Wechter W and Sies H. Quantification of the α- and γ-tocopherol metabolites 2,5,7,8-tetramethyl-2-(2′-carboxyethyl)-6-hydroxychroman and 2,7,8-trimethyl-2-(2′-carboxyethyl)-6-hydroxychroman in human serum. Analytical Biochemistry 1999; 275: 254.
23. Tsunoda M and Imai K. Analytical applications of peroxyoxalate chemiluminescence. Analytica Chimica Acta 2005; 541: 13.
24. Tsunoda M, Takezawa K, Santa T and Imai K. Simultaneous automatic determination of catecholamines and their 3-O-methyl metabolites in rat plasma by high-performance liquid chromatography using peroxyoxalate chemiluminescence reaction. Analytical Biochemistry 1999; 269: 386.
25. Tsunoda M, Takezawa K, Yanagisawa T, Kato M and Imai K. Determination of catecholamines and their 3-O-methyl metabolites in mouse plasma. Biomedical Chromatography 2001; 15: 41.
26. Tsunoda M, Nagayama M, Funatsu T, Hosoda S and Imai K. Catecholamine analysis with microcolumn LC-peroxyoxalate chemiluminescence reaction detection. Clinica Chimica Acta 2006; 366: 168.
27. Van der Vegt BJ, Lieuwes N, Cremers TIFH, de Boer SF and Koolhaas JM. Cerebrospinal fluid monoamine and metabolite concentrations and aggression in rats. Hormones and Behavior 2003; 44: 199.
28. Van Erp AMM and Miczek KA. Aggressive behavior, increased accumbal dopamine, and decreased cortical serotonin in rats. The Journal of Neuroscience 2000; 20: 9320.
29. Xu F, Gao M, Wang L and Jin L. Study on the effect of electromagnetic impulse on neurotransmitter metabolism in nerve cells by high-performance liquid chromatography electrochemical detection coupled with microdialysis. Analytical Biochemistry 2002; 307: 33.
30. Yoshitake T, Kehr J, Yoshitake S, Fujino K, Nohta H and Yamaguchi M. Determination of serotonin, noradrenaline, dopamine and their metabolites in rat brain extracts and microdialysis samples by column liquid chromatography with fluorescence detection following derivatization with benzylamine and 1,2-diphenylethylenediamine. Journal of Chromatography B 2004a; 807: 177.
31. Yoshitake T, Yoshitake S, Fujino K, Nohta H, Yamaguchi M and Kehr J. High-sensitive liquid chromatographic method for determination of neuronal release of serotonin, noradrenaline and dopamine monitored by microdialysis in the rat prefrontal cortex. Journal of Neuroscience Methods 2004b; 140: 163.
32. Yoshitake M, Nohta H, Yoshida H, Yoshitake T, Todoroki K and Yamaguchi M. Selective determination of native fluorescent bioamines through precolumn derivatization and liquid chromatography using intramolecular fluorescence resonance energy transfer detection. Analytical Chemistry 2006a; 78: 920.
33. Yoshitake T, Kehr J, Todoroki K, Nohta H and Yamaguchi M. Derivatization chemistries for determination of serotonin, norepinephrine and dopamine in brain microdialysis samples by liquid chromatography with fluorescence detection. Biomedical Chromatography 2006b; 20: 267.
34. Zhang W, Cao X, Xie Y, Ai S, Jin L and Jin J. Simultaneous determination of the monoamine neurotransmitters and glucose in rat brain by microdialysis sampling coupled with liquid chromatography-dual electrochemical detector. Journal of Chromatography B 2003; 785: 327.
35. Zhang W, Wan F, Xie Y, Gu J, Wang J, Yamamoto K and Jin L. Amperometric determination of (R)-salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters with liquid chromatography using functionalized multi-wall carbon nanotube modified electrode in Parkinson's patients' cerebrospinal fluid. Analytica Chimica Acta 2004; 512: 207.
36. Zhao YY, Jing ZZ, Wang H, Zhang HS and Yu JX. N-Hydroxysuccinimidyl phenylacetate as a novel derivatizing reagent for aliphatic amines in gas chromatography. Analytica Chimica Acta 2002; 468: 255.