Issue 6, 2002

Development of 7-(N,N-dimethylaminosulfonyl)-5-N-(4-N- aminoethyl)piperazino-2,1,3-benzoxadiazole as a water-soluble fluorogenic reagent for the sensitive liquid chromatographic determination of saturated carboxylic acids

Abstract

A reversed-phase high-performance liquid chromatographic (HPLC) method for the femtomole determination of nine saturated carboxylic acids, n-butyric (C4), n-hexanoic (C6), n-caprylic (C8), n-decanoic (C10), lauric (C12), n-tetradecanoic (C14), palmitic (C16), stearic (C18) and arachidic (C20), based on the condensation reaction of these acids with a newly synthesized water-soluble benzofurazan fluorescent reagent, 7-(N,N-dimethylaminosulfonyl)-4-N-(4-N-aminoethyl)piperazino-2,1,3-benzoxadiazole (DBD-PZ-NH2), was developed. The derivatization reaction proceeds with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC) in the presence of the catalyst 4-(dimethylamino)pyridine (DMAP). A model derivative of the reagent with n-caprylic acid (C8) was synthesized for fluorescence excitation/emission characterization. Depending on the solvents, including water, methanol, acetonitrile, 1,4-dioxane or N,N-dimethyformamide (DMF), the C8 derivative has a fluorescence emission with a fluorescence quantum yield (φ) ranging from 0.01 to 0.20 in the region from 545 to 580 nm. An exponential increase in φ was observed with increasing acetonitrile content. The calculated detection limits (signal-to-noise ratio = 3∶1) of the proposed method for the above nine carboxylic acids were 9.1, 4.0, 2.5, 2.2, 2.0, 1.8, 1.2, 1.0 and 1.3 fmol, respectively. Biological samples including Intralipos 20% and rat plasma were analysed satisfactorily.

Article information

Article type
Paper
Submitted
28 Jan 2002
Accepted
21 Mar 2002
First published
25 Apr 2002

Analyst, 2002,127, 741-747

Development of 7-(N,N-dimethylaminosulfonyl)-5-N-(4-N- aminoethyl)piperazino-2,1,3-benzoxadiazole as a water-soluble fluorogenic reagent for the sensitive liquid chromatographic determination of saturated carboxylic acids

C. Z. Huang, T. Santa and K. Imai, Analyst, 2002, 127, 741 DOI: 10.1039/B201023M

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