LIU Dan, LI Liang, LIU Cai, CHEN Xiao-yan, ZHONG Da-fang. Chromatographic Separation and Fragmentation Mechanism in Electrospray Ionization Mass Spectrometry for Colistin B Methanesulfonate[J]. Journal of Chinese Mass Spectrometry Society, 2018, 39(6): 653-662. DOI: 10.7538/zpxb.2017.0175
Citation: LIU Dan, LI Liang, LIU Cai, CHEN Xiao-yan, ZHONG Da-fang. Chromatographic Separation and Fragmentation Mechanism in Electrospray Ionization Mass Spectrometry for Colistin B Methanesulfonate[J]. Journal of Chinese Mass Spectrometry Society, 2018, 39(6): 653-662. DOI: 10.7538/zpxb.2017.0175

Chromatographic Separation and Fragmentation Mechanism in Electrospray Ionization Mass Spectrometry for Colistin B Methanesulfonate

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  • Colistin is a kind of polypeptide antibiotic, which is used for the treatment of infection caused by gram-negative bacteria. The market colistin is usually the mixture of colistin A and colistin B, and these two components show similar antibiotic activity. However, it was reported that colistin A causes much more damage to kidney than colistin B. In addition, colistin methanesulfonate is inactive prodrug of colistin, which is metabolized to colistin in vivo to kill bacteria. Colistin B methanesulfonate is a safer and more active drug compared with the mixture. There are many researches about colistin and colistin methanesulfonate. However, most of researches for colistin methanesulfonate are indirect. It is necessary to develop a method to directly study colistin B methanesulfonate. In this study, ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF MS) was used to study colistin B methanesulfonate. Acquity UPLC HSS T3 column (100 mm×2.1 mm×1.8 μm) and gradient elution were selected for better separation of colistin B with different numbers of methanesulfonic acid groups. The mass detection method for analysis of collision induced dissociation (CID) of colistin B with different numbers of methanesulfonic acid groups and deducing the possible fragmentation pathways was established. It was concluded that the retention time of colistin B with different numbers of methanesulfonic acid groups depended on the number of methanesulfonic acid groups. The more numbers of methanesulfonic acid groups were, the shorter retention time was. In addition, colistin B with different numbers of methanesulfonic acid groups could be separated well through gradient elution but isomers of the same number of methanesulfonic acid groups couldn’t be separated well because of the similar property of these isomers. It was revealed that colistin B with different numbers of methanesulfonic acid groups all had double charge quasi-molecular ion peak [M-2H]2-. CID research showed that CH2SO3, H2SO3, SO2, CH3CHO were the main neutral fragments without any amide bonds cleavage. This study provides a reference for the further study of the mass spectrometry of colistin B methanesulfonate and its derivatives, and also has a reference for the quantitative analysis and pharmacokinetic study of colistin B methanesulfonate.
  • [1]
    SATLIN M J, JENKINS S G. 151-Polymyxins[J]. Infectious Diseases, 2017, (2): 1285-1288.
    [2]
    王秀娜,张会敏,孙坚,等. 多黏菌素耐药 MCR-1:公共卫生领域的新挑战[J]. 科学通报,2017,62(10):1018-1029.WANG Xiuna, ZHANG Huimin, SUN Jian, et al. MCR-1 colistin resistance: a new challenge to global public health[J]. Chinese Science Bulletin, 2017, 62(10): 1018-1029(in Chinese) .
    [3]
    NATION R L, LI J. Colistin in the 21st century[J]. Current Opinion Infectious Diseases, 2009, 22(6): 535-543.
    [4]
    SIVANESAN S, ROBERTS K, WANG J P, et al. Pharmacokinetics of the individual major components of polymyxin B and colistin in rats[J]. Journal of Natural Products, 2017, 80(1): 225-229.
    [5]
    FDA. Colistimethate (marketed as Coly-Mycin M and generic products)[EB/OL]. (2007-06-28)[2013-08-14]. https:∥wayback. archiveit.org/7993/20170722190752/https:∥www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformati-onforPatientsandProv-iders/ucm124896.htm.
    [6]
    MERCIER T, TISSOT F, GARDIOL C, et al. High-throughput hydrophilic interaction chromatography coupled to tandem mass spectrometry for the optimized quantification of the anti-Gram-negatives antibiotic colistin A/B and its pro-drug colistimethate[J]. Journal of Chromatography A, 2014, 1 369(2): 52-63.
    [7]
    ZHAO M, WU X J, FAN Y X, et al. Development and validation of a UHPLC-MS/MS assay for colistin methanesulphonate (CMS) and colistin in human plasma and urine using weak-cation exchange solid-phase extraction[J]. Journal of Pharmaceutical and Biomedical Analysis, 2016, (124): 303-308.
    [8]
    CHENG C, LIU S R, XIAO D Q, et al. LC-MS/MS method development and validation for the determination of polymyxins and vancomycin in rat plasma[J]. Journal of Chromatography B, 2010, 878(28): 2831-2838.
    [9]
    TSAI I L, SUN H Y, CHEN G Y, et al. Simultaneous quantification of antimicrobial agentsfor multidrug-resistant bacterial infections in human plasma by ultra-high-pressure liquid chromatography-tandem mass spectrometry[J]. Talanta, 2013, 116(22): 593-603.
    [10]
    ZHAO M, CAO Y R, GUO B N, et al. LC-MS/MS determination of colistin in Mueller-Hinton broth for in vitro pharmacodynamic studies[J]. Journal of Antibiotics, 2014, 67(12): 825-829.
    [11]
    MIZUYACHI K, HARA K, WAKAMATSU A, et al. Safety and pharmacokinetic evaluation of intravenous colistin methanesulfonate sodium in Japanese healthy male subjects[J]. Current Medical Research & Opinion, 2011, 27(12): 2261-2270.
    [12]
    MA Z, WANG J P, GERBER J P, et al. Determination of colistin in human plasma, urine and other biological samples using LC-MS/MS[J]. Journal of Chromatography B, 2008, 862(1/2): 205-212.
    [13]
    王光辉,熊少祥. 有机质谱解析[M]. 北京:化学工业出版社,2005.
    [14]
    JARIWALA F B, WOOD R E, NISHSHANKA U, et al. Formation of the bisulfite anion (HSO3-, m/z 81) upon collision-induced dissociation of anions derived from organic sulfonic acids[J]. Journal of Mass Spectrometry, 2012, 47(4): 529-538.
    [15]
    BIALECKI J B, RUZICKA J, WEISBECKER C S, et al. Collision-induced dissociation mass spectra of glucosinolate anions[J]. Journal of Mass Spectrometry, 2010, 45(3): 272-283.
    [16]
    BIANCO G, LELARIO F, BATTISTA F G, et al. Identification of glucosinolates in capers by LC-ESI-hybrid linear ion trap with Fouriertransform ion cyclotron resonance mass spectrometry (LC-ESI-LTQ-FTICR MS) andinfrared multiphoton dissociation[J]. Journal of Mass Spectrometry, 2012, 47(9): 1160-1169.
    [17]
    BEN-ARI J, ETINGER A, WEISZ A, et al. Hydrogen-shift isomerism: mass spectrometry ofisomeric benzenesulfonate and 2-, 3- and 4- dehydrobenzenesulfonic acid anions in the gas phase[J]. Journal of Mass Spectrometry, 2005, 40(8): 1064-1071.
    [18]
    SUN M J, DAI W N, LIU D Q. Fragmentation of aromatic sulfonamides inelectrospray ionization mass spectrometry: eliminationof SO2 via rearrangement[J]. Journal of Mass Spectrometry, 2008, 43(3): 383-393.
    [19]
    王慧心. 钠离子化肽在电喷雾质谱低能量碰撞下碎裂规律的研究[D]. 长春:吉林大学,2015.
    [20]
    WANG H X, WANG B, WEI Z L, et al. Characteristic neutral loss of CH3CHO from Thr-containing sodium-associated peptides[J]. Journal of Mass Spectrometry, 2014, 50(3): 488-494.

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