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Titolo:
Development of water-soluble fluorogenic reagents having a 2,1,3-benzoxadiazole structure and their application to the determination of peptides
Autore:
Kajiro, T; Fukushima, T; Santa, T; Imai, K;
Indirizzi:
Univ Tokyo, Grad Sch Pharmaceut Sci, Lab Bioanalyt Chem, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo Tokyo Japan 1130033 lyt Chem, Bunkyo Ku, Tokyo 1130033, Japan
Titolo Testata:
ANALYST
fascicolo: 6, volume: 125, anno: 2000,
pagine: 1115 - 1121
SICI:
0003-2654(2000)125:6<1115:DOWFRH>2.0.ZU;2-P
Fonte:
ISI
Lingua:
ENG
Soggetto:
PERFORMANCE LIQUID-CHROMATOGRAPHY; INDUCED FLUORESCENCE DETECTION; PRECOLUMN DERIVATIZATION; SENSITIVE DETERMINATION; HUMAN PLASMA; SEPARATION; THIOLS; ELECTROPHORESIS; IDENTIFICATION; DERIVATIVES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
28
Recensione:
Indirizzi per estratti:
Indirizzo: Imai, K Univ Tokyo, Grad Sch Pharmaceut Sci, Lab Bioanalyt Chem, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan Univ Tokyo 7-3-1 Hongo Tokyo Japan 1130033 , Tokyo 1130033, Japan
Citazione:
T. Kajiro et al., "Development of water-soluble fluorogenic reagents having a 2,1,3-benzoxadiazole structure and their application to the determination of peptides", ANALYST, 125(6), 2000, pp. 1115-1121

Abstract

Water-soluble fluorogenic reagents having a 2,1,3-benzoxadiazole (benzofurazan) structure, 2-(7-fluoro-2,1,3-benzoxadiazole-4-sulfonamido)ethanesulfonic acid (ES-ABD-F), 4-(7-fluoro-2,1,3-benzoxadiazole-4-sulfonamido)benzenesulfonic acid (p-BS-ABD-F) and 3-(7-fluoro-2,1,3-benzoxadiazole-4-sulfonamido)benzenesulfonic acid (m-BS-ABD-F), were synthesized and evaluated for their fluorescence characteristics and reactivities with peptides. Although these reagents showed no fluorescence, their derivatives with valine exhibited fluorescence at maximum wavelengths from 562 to 566 nm with excitation from 424 to 426 nm. The derivatives with ES-ABD-F and m-BS-ABD-F showed a similar sensitivity to that of 4-(N,N-dimethylaminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole (DBD-F), a previously developed fluorogenic reagent for aminocompounds. The fluorescence intensity obtained with the p-BS-ABD-F derivative was about one-third of that of the others. Angiotensin II (ANG II), an octapeptide, was successfully derivatized with ES-ABD-F and m-BS-ABD-F and determined by using high performance liquid chromatography (HPLC) with fluorescence detection. Good linearity was obtained between the amount of peptide (1-200 pmol) and the peak area of their derivatives (correlation coefficients > 0.999). The detection limits of the ANG II derivatives with ES-ABD-F and m-BS-ABD-F were 210 and 270 fmol, respectively. m-BS-ABD-F, however, showed some disadvantages in the simultaneous determination of peptides: a possible interference with the separation of derivatized peptides due to some blank peaks, and its complicated and changeable pH-reactivity profile. From these results, ES-ABD-F was recommended for the sensitive and simultaneous determination of peptides. The derivatization reaction with ES-ABD-F commonly reached a plateau at 60 degrees C and pH > 8.5 for several hours. The peptide derivatives of ES-ABD-F (ANG I, ANG II, ANG III, bradykinin, and substance P) were well separated by reversed phase HPLC. In addition, the amyloid beta-peptide (1-40) [A beta(1-40)] derivative with ES-ABD-F was successfully eluted from a YMC-pack C4 (150 x 4.6 mm id, 5 mu m particle size) under conditions such that underivatized A beta(1-40) was not eluted, suggesting that the derivatization with ES-ABD-F decreased the adsorption of hydrophobic peptides to the HPLC stationary phase.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/04/20 alle ore 21:45:32