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

Fukushima

Ichibangase

et al. 2007

Self Cite

Chemical derivatization is often used to enhance the detectability of the target compounds and to improve the separation efficiency in high-performance liquid chromatography (HPLC). In this review, we describe the recent progress in the development of derivatization reagents having a benzofurazan structure, namely, the fluorogenic reagents, water-soluble reagents, reagents for the analysis of peptides and proteins, and reagents for mass spectrometric detection. The application of these reagents to bio-samples is also briefly described.

Section: Water-soluble Reagents (Table 3)mentioning

confidence: 99%

Recent progress in the development of derivatization reagents having a benzofurazan structure

Fukushima

Ichibangase

et al. 2007

Self Cite

“…Furthermore, reagents bearing a negative charge such as 2-(7-fluoro-2,1,3-benzoxadiazole-4-sulfonamido)ethanesulfonic acid (ES-ABD-F; Kajiro et al, 2000) for amines and ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F; Imai et al, 1983) for thiols have been developed. We have also reported the reagent bearing a positive charge, 7-(N,N,-dimethylaminosulfonyl)-4-N-(4-N-aminoethyl)piperazino-2,1,3-benzoxadiazole (DBD-PZ-NH 2 ; Huang et al, 2002), for carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Matsumura

Huang

et al. 2002

Self Cite

A hydrophilic fluorescent derivatization reagent for fatty acids, 4-N-(4-N-aminoethyl)piperazino-7-nitro-2,1,3-benzoxadiazole (NBD-PZ-NH 2 ), was designed and synthesized. NBD-PZ-NH 2 possesses not only a fluorophore and a reacting group but also a positive charge group and, thus, was hydrophilic and suitable for application to capillary electrophoresis. NBD-PZ-NH 2 reacted with fatty acids in the presence of triphenylphosphine (TPP) and 2,2'-dipyridyl disulfide (DPDS) at room temperature within 10 min. The derivatives were strongly fluoresced and were positively charged at pH below 3. The derivatives of C4-C20 fatty acids were separated within 10 min in 50% acetonitrile in water containing 30 mM ammonium acetate and 1.0 M acetic acid by capillary electrophoresis with laser-induced fluorescence (CE-LIF) detection. The detection limits attained were 6.5 nM (signal-to-noise ratio of 3). It is proposed that NBD-PZ-NH 2 is a prominent derivatization reagent for fatty acids which is suitable for CE-LIF application.

“…We have already developed several fluorescent benzofurazan derivatization reagents (Uchiyama et al, 2001) and reported that the benzofurazan compounds were sensitively analyzed by LC/ MS (Santa et al, 1998;Masuda et al, 2004;Tsukamoto et al, 2005). In this study, we adopted DBD-PZ-NH 2 (Huang et al, 2002) as a derivatization reagent. By changing six protons in the dimethylamino group to deuteriums, the heavy form of DBD-PZ-NH 2 was synthesized.…”

Section: Synthesis Of the Derivatization Reagentmentioning

confidence: 99%

“…DBD-PZ-NH 2 (D) was synthesized according to the previous paper (Huang et al, 2002). DBD-Cl (D) (82 mg) was dissolved in 8 mL acetonitrile.…”

Section: Dbd-pz-nh 2 (D)mentioning

confidence: 99%

Synthesis of the isotope‐labeled derivatization reagent for carboxylic acids, 7‐(N,N‐dimethylaminosulfonyl)‐4‐(aminoethyl)piperazino‐2,1,3‐benzoxadiazole (d₆) [DBD‐PZ‐NH₂ (D)], and its application to the quantification and the determination of relative amount of fatty acids in rat plasma samples by high‐performance liquid chromatography/mass spectrometry

Tsukamoto

Yoshida

et al. 2005

Self Cite

The isotope-labeled benzofurazan derivatization reagent for carboxylic acids, 7-(N,N-dimethylaminosulfonyl)-4-(aminoethyl)piperazino-2,1,3-benzoxadiazole (d6) [DBD-PZ-NH2 (D)] was synthesized. DBD-PZ-NH2 (D) was used for the accurate quantification of fatty acids by liquid chromatography/mass spectrometry (LC/MS). The standard fatty acids were derivatized with DBD-PZ-NH2 (D) to the stable isotope-labeled compounds for the fatty acids derivatives of DBD-PZ-NH2 and used for the internal standards. The obtained calibration curves for fatty acids were linear over the range 0.1-200 microM (r2 > 0.999). Fatty acids in plasma samples were determined after derivatization with DBD-PZ-NH2 and analyzed by LC/MS using standard fatty acid DBD-PZ-NH2 (D) derivatives as internal standards. Furthermore, the relative amounts of fatty acids in two plasma samples were determined after derivatization with DBD-PZ-NH2 and DBD-PZ-NH2) (D). The isotope-labeled derivatization reagent was useful for accurate quantification and the determination of relative amounts of the metabolites in biological samples having the target functional group.