电喷雾离子阱质谱对具有强镇痛活性的新型双螺环哌嗪季铵盐的裂解方式研究

doi:10.5246/jcps.2011.01.006

电喷雾离子阱质谱对具有强镇痛活性的新型双螺环哌嗪季铵盐的裂解方式研究

王欣, 李昂, 王玮, 李润涛^*

北京大学医学部天然药物及仿生药物国家重点实验室; 药学院化学生物学系, 北京 100191

收稿日期:2010-11-17 修回日期:2010-12-15 出版日期:2011-01-15 发布日期:2011-01-15
通讯作者: 李润涛*

Fragmentation patterns of novel dispirocyclopiperazinium dibromides during electrospray ionization mass spectrometry

Xin Wang, Ang Li, Wei Wang, Run-Tao Li^*

State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2010-11-17 Revised:2010-12-15 Online:2011-01-15 Published:2011-01-15
Contact: Run-Tao Li*

摘要/Abstract

摘要：

我们研究了具有镇痛活性的螺环哌嗪季铵盐二溴代物1a-1e的一级和二级质谱。化合物1脱去溴负离子生成[M-Br]⁺峰2, 离子2脱去溴化氢分子形成离子峰4, 离子[M-Br-44]⁺ 3为基峰。化合物1d-1e由于是酰胺类化合物, 除了上述几类峰外, 还生成了离子碎片[M-2Br-33]⁺。

关键词: 质谱, 双螺环哌嗪季铵盐溴化物, 裂解规律

Abstract:

The fragmentation patterns of a series of dispirocyclopiperazinium dibromides with strong analgesic activity during positive ion electrospray ionization mass spectrometry were analyzed. The [M-Br]⁺ 2 ions showed the characteristic isotopic peaks and were assigned as the molecular ions. The loss of a 44 Dalton unit from 2 produced ion 3 [M-Br-44]⁺and the loss of HBr from 2 formed ion 4. Besides, the carbamates 1d-1e produced extra ions [M-2Br-33]⁺. The related fragmentation mechanisms were proposed.

Key words: Mass spectrometry, Dispirocyclopiperazinium dibromides, Fragmentation pathway

中图分类号:

R917

Supporting:

Foundation item: National Natural Science Foundation of China (Grant No. 20772009).
^*Corresponding author. Tel.: 86-10-82801504

王欣, 李昂, 王玮, 李润涛^* . 电喷雾离子阱质谱对具有强镇痛活性的新型双螺环哌嗪季铵盐的裂解方式研究[J]. , DOI: 10.5246/jcps.2011.01.006.

Xin Wang, Ang Li, Wei Wang, Run-Tao Li^* . Fragmentation patterns of novel dispirocyclopiperazinium dibromides during electrospray ionization mass spectrometry[J]. , DOI: 10.5246/jcps.2011.01.006.

参考文献

[1] Decker, M.W.; Meyer, M.D. Biochem. Pharmacol. 1999, 58, 917-923.
[2] Kowaluk, E.A.; Lynch, K.J.; Jarvis, M.F. Annu. Rep. Med. Chem. 2000, 35, 21-30.
[3] Spande, T.F.; Garraffo, M.; Edwards, M.W.; Yeh, J.C.; Pannell, L.; Daly, J.W. J. Am. Chem. Soc. 1992, 114, 3475-3478.
[4] Qian, C.G.; Li, T.C.; Shen, T.Y.; Libertine-Garahan, L.; Eckman, J.; Biftu, T.; Ip, S. Eur. J. Pharmacol. 1993, 250, R13-R14.
[5] Rupniak, N.M.J.; Patel, S.; Marwood, R.; Webb, J.; Traynor, J.R.; Elliott, J.; Freedman, S.B.; Flechter, S.R.; Hill, R.G. Br. J. Pharmacol. 1994, 113, 1487-1493.
[6] Kizawa, Y.; Takayanagi, I. Gen. Pharmacol. 1984, 15, 149-150.
[7] Lippiello, P.M.; Fernandes, K.G. Mol. Pharmacol. 1986, 29, 448-454.
[8] De Fiebre, C.M.; Meyer, E.M.; Henry, J.C.; Muraskin, S.I.; Kem, W.R.; Papke, R.L. Mol. Pharmacol. 1995, 47, 164-171.
[9] Li, R.T.; Chen, H.C.; Yang, J.Z. Acta Pharm. Sin. 1995, 30, 63-69.
[10] Li, R.T.; Cui, J.L.; Cheng, T.M.; Cai, M.S. Acta Pharm. Sin. 1999, 34, 666-668.
[11] Li, R.T.; Cai, J.C.; Tang, X.C.; Cai, M.S. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 179-181.
[12] Ge, Z.M.; Li, R.T.; Cheng, T.M.; Cui, J.R. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 173-176.
[13] Wang, X.; Gao, F.L.; Piao, H.B.; Cheng, T.M.; Li, R.T. Bioorg. Med. Chem. Lett. 2003, 13, 1729-1732.
[14] Gao, F.L.; Wang, X.; Zhang, H.M.; Cheng, T.M.; Li, R.T. Bioorg. Med. Chem. Lett. 2003, 13, 1535-1537.
[15] Li, A.; Wang, X.; Yue, C.Q.; Ye, J.; Li, C.L.; Li, R.T. Bioorg. Med. Chem. Lett. 2007, 17, 5078-5081.
[16] Barcelo, D.; Durand, G.; Vreeken, R.J. J. Chromatogr. A. 1993, 647, 271-277.
[17] Tondeur, Y.; Sovocool, G.W.; Mitchum, R.K.; Niederhut, W.J.; Donnelly, J.R. Biomed. Environ. Mass Spectrom. 1987, 14, 733-736.
[18] Evans, C.S.; Startin, J.R.; Goodall.; D.M.; Keely, B.J. Rapid Commun. Mass Spectrom. 2000, 14, 112-117.
[19] Taguchi, V.Y.; Jenkins, S.W.D.; Crozier, P.W.; Wang, D.T. J. Am. Soc. Mass Spectrom. 1998, 9, 830-839.
[20] Marr, J.C.; King, J.B. Rapid Commun. Mass Spectrom. 1997, 11, 479-483.
[21] Castro, R.; Moyano, E.; Galceran, M.T. J. Chromatogr. A. 1999, 830, 145-154.
[22] Song, X.; Budde, W.L. J. Am. Soc. Mass Spectrom. 1996, 7, 981-986.
[23] Moyano, E.; Games, D.E.; Galceran, M.T. Rapid Commun. Mass Spectrom. 1996, 10, 1379-1385.