Catecholamines derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole: characterization of chemical structure and fluorescence properties

Zhu, Xunlin, Shaw, P. Nicholas and Barrett, David A. (2003) Catecholamines derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole: characterization of chemical structure and fluorescence properties. Analytica Chimica Acta, 478 2: 259-269.


Author Zhu, Xunlin
Shaw, P. Nicholas
Barrett, David A.
Title Catecholamines derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole: characterization of chemical structure and fluorescence properties
Journal name Analytica Chimica Acta   Check publisher's open access policy
ISSN 0003-2670
Publication date 2003
Sub-type Article (original research)
DOI 10.1016/S0003-2670(02)01515-5
Volume 478
Issue 2
Start page 259
End page 269
Total pages 11
Place of publication Amsterdam
Publisher Elsevier Science Bv
Language eng
Subject 0301 Analytical Chemistry
Abstract 4-Fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) was evaluated as a fluorogenic derivatization reagent for the analysis of the catecholamines, dopamine, epinephrine, norepinephrine, and their naturally occurring metabolites, metanephrine and normetanephrine, homovanillic acid, 3,4-dihydroxyphenyl acetic acid. These compounds reacted rapidly with NBD-F under mild conditions to form stable derivatives. The optimal reaction conditions were found to be 12.5 mM borate buffer pH 8.0 in water:acetonitrile (1:1) at 50 degreesC for 5 min. New NBD derivatives of all the catecholamines and metabolites were prepared and purified and were shown by electrospray mass spectrometry to be fully reacted at all available catechol and amine sites, resulting in di- or tri-substituted derivatives. Homovanillic acid and 3,4-dihydroxyphenyl acetic acid reacted with NBD-F but gave non-fluorescent derivatives. The fluorescence excitation wavelength maximum demonstrated a red shift for the derivatives with increasing polarity of the solvent and the fluorescence intensity increased linearly with increasing organic ratio in the solvent-aqueous buffer complex. The presence of electrolyte in the solvent and the electrolyte concentration in the solvent-electrolyte complex had little effect on the fluorescent intensity. The fluorescence quantum yields in acetonitrile were also obtained. The separation behavior of the NBD-catecholamines was determined by high-performance liquid chromatography (HPLC). The studies demonstrated good potential for the application of NBD-F derivatization to the quantitative analysis of catecholamines and related compounds in biological matrices. (C) 2002 Elsevier Science B.V. All rights reserved.
Keyword Chemistry, Analytical
NBD-F
fluorescence
norepinephrine
epinephrine
dopamine
metanephrine
normetanephrine
chromatography
quantum yield
Performance Liquid-chromatography
Capillary-electrophoresis
Benzofurazan Compounds
Amino-acids
4-fluoro-7-nitrobenzo-2-oxa-1,3-diazole
Metabolites
Pheochromocytoma
Proteins
Plasma
Cells
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Pharmacy Publications
 
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