Syntheses of Fluorescence Probe 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one and Its Application for the Determination of Aliphatic Amines with LC-APCI-MS

Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (11): 2146.

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Syntheses of Fluorescence Probe 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one and Its Application for the Determination of Aliphatic Amines with LC-APCI-MS

FU Yan-Yan² , SUN Zhi-Wei^1,3, ZHAO Huai-Xin², BAI Xin-Wei² , SUO You-Rui¹ , LI Yu-Lin¹, YOU Jin-Mao^1,2*

1. Northwest Plateau Institute of Biology, Chinese Academy of Sciences, Xining 810001, China;
2. Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China;
3. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China

Received:2009-06-24 Online:2009-11-10 Published:2009-11-10
Contact: YOU Jin-Mao. E-mail: jmyou6304@163.com
Supported by:
国家自然科学基金(批准号: 20075016)和中国科学院“百人计划”项目(批准号: 328)资助.

Abstract

Abstract:

2-{12-Oxobenzo[b]acridin-5(12H)-yl}-acetic acid(BAAA) reacted with coupling agent N,N′-carbonyldiimidazole(CDI) to form an activated amide intermediate 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one(IEBA), which was a novel fluorescence probe. The amide intermediate(IEBA) reacted preferably with amines in DMF solvent in the absence of catalysts to give the high yields of derivatives, which not only have high fluorescence sensitivity but also have strong ionizable ability. The optimum excitation and emission wavelengths were at λ_ex/λ_em=272 nm/505 nm. The percent ionization δ values in aqueous acetonitrile and aqueous methanol were in the range of 0—57.32% and 0—62.14%, respectively. The fluorescence detection limits of twelve amine derivatives(at a signal-to-noise ratio of 3) were in the range of 0.15—0.50 ng/mL. The online APCI-MS detection limits were at levels of 1.43—8.51 ng/mL(S/N=3).

Key words: High performance liquid chromatography/ion-trap mass spectrometry; Percent ionization; 2-{12-Oxobenzo[b]acridin-5(12H)-yl}-acetic acid; 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one

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FU Yan-Yan, SUN Zhi-Wei, ZHAO Huai-Xin, BAI Xin-Wei , SUO You-Rui , .... Syntheses of Fluorescence Probe 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one and Its Application for the Determination of Aliphatic Amines with LC-APCI-MS[J]. Chem. J. Chinese Universities, 2009, 30(11): 2146.

References

[1]Belin L., Wass U., Audunsson G., et al.. Br. J. Med.[J], 1983, 40(3): 251—257
[2]Gao C. X., Krull I. S., Trainor T.. J. Chromatogr. Sci.[J], 1990, 28(3): 102—08
[3]Dalene M., Lundh T., Mathiasson L.. J. Chromatogr.[J], 1985, 322: 169—176
[4]Önal A.. Food Chem.[J], 2007, 103: 1475—1486
[5]Yurchenko S., Mlder U.. Food Chem.[J], 2007, 100: 1713—1721
[6]Yurchenko S., Mlder U.. Food Chem.[J], 2006, 96: 325—333
[7]Deng C., Li N., Wang L., et al.. J. Chromatogr. A[J], 2006, 1131: 45—50
[8]Casella I. G., Palladino G. A., Contursi M.. J. Sep. Sci.[J], 2008, 31: 3718—3726
[9]Motte J. C., Windy R., Delafortrie A.. J. Chromatogr. A[J], 1996, 728: 333—341
[10]Ahnoff M., Grundevik I., Arfwidsson A., et al.. Anal. Chem.[J], 1981, 53(2): 485—489
[11]You J., Zhao W., Liu L., et al.. Talanta[J], 2007, 72: 914—925
[12]You J., Liu L., Zhao W., et al.. Anal. Bioanal. Chem.[J], 2007, 387: 2705—2718
[13]CHEN Xiang-Ming(陈向明), SHI Yun-Wei(石运伟), ZHAO Xian-En(赵先恩), et al.. Chinese Journal of Chromatography(色谱)[J], 2005, 23(6): 642—645
[14]ZHAO Xian-En(赵先恩), LI Yu-Lin(李玉林), YOU Jin-Mao(尤进茂), et al.. Chinese Journal of Analytical Chemistry(分析化学)[J], 2007, 35(6): 779—785
[15]Allen C. F. H., Alan B.. Organic Syntheses[J], 1942, 22: 19—23
[16]Marthaed W.. The Merck Index, 11th Ed.[M], Rahway: Merck & Co. Inc., 1988: 7290
[17]Shirley D. A., Tatum W. E.. J. Org. Chem.[J], 1960, 25(12): 2238—2240
[18]XU Jin-Jun(许金钧), WANG Zun-Ben(王尊本). Fluorescence Analysis, 3rd Ed.(荧光分析法, 第三版)[M], Beijing: Science Press, 2006: 49—61
[19]You J., Zhang W., Zhang Q., et al.. Anal. Chem.[J], 2002, 74: 261—269
[20]ZHAO Huai-Xin(赵怀鑫), SUN Xue-Jun(孙学军), SUN Zhi-Wei(孙志伟), et al.. Chem. J. Chinese Universities(高等学校化学学报)[J], 2009, 30(4): 675—681

Syntheses of Fluorescence Probe 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one and Its Application for the Determination of Aliphatic Amines with LC-APCI-MS

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