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首页> 外文期刊>Journal of mass spectrometry: JMS >Fragmentation pathways of deprotonated amide-sulfonamide CXCR4 inhibitors investigated by ESI-IT-MSn, ESI-Q-TOF-MS/MS and DFT calculations
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Fragmentation pathways of deprotonated amide-sulfonamide CXCR4 inhibitors investigated by ESI-IT-MSn, ESI-Q-TOF-MS/MS and DFT calculations

机译：由ESI-IT-MSN，ESI-Q-TOF-MS / MS和DFT计算研究的去质子化酰胺 - 磺酰胺CXCR4抑制剂的碎片途径

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摘要

Amide-sulfonamides provide a potent anti-inflammatory scaffold targeting the CXCR4 receptor. A series of novel amide-sulfonamide derivatives were investigated for their gas-phase fragmentation behaviors using electrospray ionization ion trap mass spectrometry and quadrupole time-of-flight mass spectrometry in negative ion mode. Upon collision-induced dissociation (CID), deprotonated amide-sulfonamides mainly underwent either an elimination of the amine to form the sulfonyl anion and amide anion or a benzoylamide derivative to provide sulfonamide anion bearing respective substituent groups. Based on the characteristic fragment ions and the deuterium-hydrogen exchange experiments, three possible fragmentation mechanisms corresponding to ion-neutral complexes including [sulfonyl anion/amine] complex (INC-1), [sulfonamide anion/benzoylamide derivative] complex (INC-2) and [amide anion/sulfonamide] complex (INC-3), respectively, were proposed. These three ion-neutral complexes might be produced by the cleavages of S-N and C-N bond from the amide-sulfonamides, which generated the sulfonyl anion (Route 1), sulfonamide anion (Route 2) and the amide anion (Route 3). DFT calculations suggested that Route 1, which generated the sulfonyl anion (ion c) is more favorable. In addition, the elimination of SO2 through a three-membered-ring transition state followed by the formation of C-N was observed for all the amide-sulfonamides.
机译：酰胺 - 磺酰胺提供靶向CXCR4受体的有效的抗炎支架。研究了一种使用电喷雾电离离子捕集物质谱法和四极其飞行时间质谱法研究了一系列新的酰胺 - 磺胺胺衍生物，以负离子模式。在碰撞诱导的解离（CID）后，反质酰胺 - 磺酰胺主要经历了胺的消除以形成磺酰阴离子和酰胺阴离子或苯酰胺衍生物，以提供亚磺酰胺阴离子的亚胺，其具有相应的取代基。基于特征性片段离子和氘 - 氢气交换实验，对应于离子 - 中性配合物的三种可能的碎片机制，包括[磺酰阴离子/胺]复合物（Inc-1），[磺酰胺阴离子/苯氧酰胺衍生物]复合物（Inc-2 [分别]提出了[酰胺阴离子/磺酰胺]复合物（Inc-3）。这三个离子中性复合物可以通过从酰胺 - 磺胺酰胺的S-N和C-N键的切割产生，该磺酰胺产生，其产生磺酰阴离子（途径1），磺酰胺阴离子（途径2）和酰胺阴离子（途径3）。 DFT计算表明，导线1，产生磺酰阴离子（离子C）更有利。另外，对于所有酰胺 - 磺酰胺，观察到通过三元环过渡状态消除SO2通过三元环过渡状态。

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  • 来源
    《Journal of mass spectrometry: JMS》 |2019年第11期|共9页
  • 作者

    Guo Zili; Jie Xiaokang; Zhu Peixi; Sun Jian; Gu Jinping; Su Feng; Bai Renren; Xie Yuanyuan;

  • 作者单位

    Zhejiang Univ Technol Key Lab Green Pharmaceut Technol &

    Related Equipm Minist Educ Hangzhou Zhejiang Peoples R China;

    Zhejiang Univ Technol Coll Pharmaceut Sci Hangzhou 310014 Zhejiang Peoples R China;

    Zhejiang Univ Technol Coll Pharmaceut Sci Hangzhou 310014 Zhejiang Peoples R China;

    Zhejiang Univ Technol Coll Pharmaceut Sci Hangzhou 310014 Zhejiang Peoples R China;

    Zhejiang Univ Technol Coll Pharmaceut Sci Hangzhou 310014 Zhejiang Peoples R China;

    Zhejiang Univ Technol Coll Pharmaceut Sci Hangzhou 310014 Zhejiang Peoples R China;

    Zhejiang Univ Technol Coll Pharmaceut Sci Hangzhou 310014 Zhejiang Peoples R China;

    Zhejiang Univ Technol Key Lab Green Pharmaceut Technol &

    Related Equipm Minist Educ Hangzhou Zhejiang Peoples R China;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 分析化学;
  • 关键词

    amide-sulfonamides; deuterium-hydrogen exchange; DFT calculations; ESI-QTOF-MS; MS; fragmentation pathways;

    机译：酰胺 - 磺胺酰胺;氘 - 氢交换;DFT计算;ESI-QTOF-MS;MS;碎片途径;

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