氟喹诺酮酸酯的ESI-MS裂解研究
Study on the ESI-MS Dissociation of Fluoroquinolone Acid Esters
DOI: 10.12677/JOCR.2018.62007, PDF,    科研立项经费支持
作者: 陈嘉豪, 莫洛淇, 雷颖欣, 游权稳, 汤日元*:华南农业大学,材料与能源学院应用化学系,广东 广州
关键词: 喹诺酮脱羧偶联质谱Quinolones Decarboxylation Coupling Mass Spectrometry
摘要: 氟喹诺酮酸酯对养殖业和人类健康存在潜在危害,发展其分析检测方法具有重要的意义。本论文制备了七种氟喹诺酮酸酯,并在ESI质谱仪的正离子测试模式下,获取它们的MS2裂解图谱。结果显示七种氟喹诺酮酸酯均优先断裂酯基中的C-O键,产生三种高强度的碎片离子峰:[M+H]+、[M+2H-Y]+和[M-Y-16]+ (Y为酯基中烷基的质量数)。这些碎片可以作为定性离子,用于鉴定氟喹诺酮酸酯。
Abstract: Fluoroquinolone acid esters have potential hazards to the breeding industries and human health, so it is of vital significance to develop its analysis and detection methods. In this paper, seven kinds of fluoroquinolone acid esters were prepared. The ESI-MS2 dissociation spectrograms of these compounds were obtained under the positive ions test mode of mass spectrometry. The results showed that the C-O bonds of ester groups in these fluoroquinolone acid esters were preferentially fractured. Three fragmentation ion peaks with high intensities were found. It includes [M+H]+, [M+2H-Y]+, and [M-Y-16]+ (Y refers to the mass number of alkyl groups in ester groups). These fragmentation ions could be used as qualitative ions for the identification of fluoroquinolone acid esters.
文章引用:陈嘉豪, 莫洛淇, 雷颖欣, 游权稳, 汤日元. 氟喹诺酮酸酯的ESI-MS裂解研究[J]. 有机化学研究, 2018, 6(2): 45-51. https://doi.org/10.12677/JOCR.2018.62007

参考文献

[1] Salvaggio, F., Hodgkinson, J.T., Carro, L., et al. (2016) The Synthesis of Quinolone Natural Products from Pseudonocardia sp. Eu-ropean Journal of Organic Chemistry, 2016, 434-437.
[Google Scholar] [CrossRef
[2] Abe, H., Kawada, M., Inoue, H., et al. (2013) Synthesis of Intervenolin, an Antitumor Natural Quinolone with Unusual Substituents. Organic Letters, 15, 2124-2127.
[Google Scholar] [CrossRef] [PubMed]
[3] Sun, J., Zhu, H., Yang, Z.M., et al. (2013) Synthesis, Molecular Modeling and Biological Evaluation of 2-Aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole-2(3H)-thione Quinolone Derivatives as Novel An-ticancer Agent. Cheminform, 60, 23-28.
[4] Suthar, S.K., Jaiswal, V., Lohan, S., et al. (2013) Novel Quinolone Substituted Thia-zolidin-4-Ones as Anti-Inflammatory, Anticancer Agents: Design, Synthesis and Biological Screening. European Journal of Medicinal Chemistry, 63, 589-602.
[Google Scholar] [CrossRef] [PubMed]
[5] Li, J., Zheng, T.C., Jin, Y., et al. (2018) Synthesis, Molecular Docking and Biological Evaluation of Quinolone Derivatives as Novel Anticancer Agents. Chemical & Pharmaceutical Bulletin, 66, 55-60.
[Google Scholar] [CrossRef] [PubMed]
[6] Yan, L., Liu, D., Wang, X.H., et al. (2017) Bacterial Plasmid-Mediated Quinolone Resistance Genes in Aquatic Environments in China. Scientific Reports, 7, Article ID: 40610.
[7] Rodriguez, C.N., Rodriguezmorales, A.J., Garcia, A., et al. (2005) Quinolone Antimicrobial Resistance in Some Enterobacteria: A 10-Year Study in a Venezuelan General Hospital. International Journal of Antimicrobial Agents, 25, 546-550.
[Google Scholar] [CrossRef] [PubMed]
[8] Correia, S., Poeta, P., Igrejas, G., et al. (2017) Mechanisms of Quinolone Action and Resistance: Where Do We Stand? Journal of Medical Microbiology, 66, 551-559.
[Google Scholar] [CrossRef] [PubMed]
[9] Robicsek, A., Jacoby, G.A. and Hooper, D.C. (2006) The Worldwide Emergence of Plasmid-Mediated Quinolone Resistance. Lancet Infectious Diseases, 6, 629-640.
[Google Scholar] [CrossRef
[10] 孙慧萍, 蔡力力, 阎赋琴, 等. 喹诺酮类药物的作用机制及不良反应[J]. 中华医院感染学杂志, 2008, 18(7): 1014-1016.
[11] Samyde, J., Petit, P., Hillaire-Buys, D., et al. (2016) Quinolone Antibiotics and Suicidal Behavior: Analysis of the World Health Organization’s Adverse Drug Reactions Database and Discussion of Potential Mechanisms. Psychopharmacology, 233, 2503-2511.
[Google Scholar] [CrossRef] [PubMed]
[12] Kang, J., Wang, L., Chen, X.L., et al. (2001) Interactions of a Series of Fluoroquinolone Antibacterial Drugs with the Human Cardiac K+ Channel HERG. Molecular Pharmacology, 59, 122-126.
[Google Scholar] [CrossRef] [PubMed]
[13] 饶勇, 曾振灵, 杨桂香, 等. 液相色谱–质谱联用检测牛奶中氟喹诺酮类药物残留的确证方法[J]. 中国农业科学, 2007, 40(5): 1033-1041.
[14] 赵扬, 郑志明, 金社胜, 等. 液质联用法同时测定猪粪便中16种(氟)喹诺酮类药物残留[J]. 农业环境科学学报, 2011, 30(6): 1248-1253.
[15] 刘博, 薛南冬, 杨兵, 等. 高效液相色谱–荧光检测法同时分析鸡粪中六种氟喹诺酮类抗生素[J]. 农业环境科学学报, 2014, 33(5): 1050-1056.
[16] 农业部决定在食品动物中停止使用洛美沙星等4种兽药(中华人民共和国农业部公告第2292号) [J]. 中国兽药杂志, 2015, 49(9): 40.
[17] Zhang, J.-R., Liao, Y.-Y., Deng, J.-C., Tang, Z.-L., Xu, Y.-L., Xu, L. and Tang, R.-Y. (2017) DABCO-Promoted Decarboxylative Acylation: Synthesis of α-Keto and α,β-Unsaturated Amides or Esters. Asian Journal of Organic Chemistry, 6, 305-312.
[Google Scholar] [CrossRef
[18] 郑亚杰. 基于LC-MS/MS方法的喹诺酮类药物的杂质谱研究[D]: [博士学位论文]. 北京: 北京协和医学院, 2014.
[19] 李婧. 氟喹诺酮类抗生素的直接质谱分析研究[D]: [硕士学位论文]. 南昌: 东华理工大学, 2015.
[20] 郭泽琴. 几种喹诺酮类原料药影响因素的液-质联用技术分析[D]: [硕士学位论文]. 重庆: 重庆大学, 2014.