7-((methylsulfonyl)thio)heptanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-((methylsulfonyl)thio)heptanoic acid
• 英文别名: 6-carboxyhexyl methanethiosulfonate；7-Methylsulfonylsulfanylheptanoic acid；7-methylsulfonylsulfanylheptanoic acid
• 化学式: C₈H₁₆O₄S₂
• 分子量: 240.345
• InChiKey: IEKCWFGCRPNVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-((methylsulfonyl)thio)heptanoic acid 在 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.03h， 生成 S-(7-(hydroxyamino)-7-oxoheptyl)methanesulfonothioate
  参考文献：
  名称：

  Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

  摘要：

  Botulinum neurotoxins have remarkable persistence (similar to weeks to months in cells), outlasting the small-molecule inhibitors designed to target them. To address this disconnect, inhibitors bearing two pharmacophores.a zinc binding group and a Cys-reactive warhead.were designed to leverage both affinity and reactivity. A series of first-generation bifunctional inhibitors was achieved through structure-based inhibitor design. Through X-ray crystallography, engagement of both the catalytic Zn2+ and Cys165 was confirmed. A second-generation series improved on affinity by incorporating known reversible inhibitor pharmacophores; the mechanism was confirmed by exhaustive dialysis, mass spectrometry, and in vitro evaluation against the C165S mutant. Finally, a third-generation inhibitor was shown to have good cellular activity and low toxicity. In addition to our findings, an alternative method of modeling time-dependent inhibition that simplifies assay setup and allows comparison of inhibition models is discussed.

  DOI：

  10.1021/acs.jmedchem.0c01006
• 作为产物：
  描述：

  7-溴庚酸 、 硫甲磺酸钠 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到7-((methylsulfonyl)thio)heptanoic acid
  参考文献：
  名称：

  Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

  摘要：

  Botulinum neurotoxins have remarkable persistence (similar to weeks to months in cells), outlasting the small-molecule inhibitors designed to target them. To address this disconnect, inhibitors bearing two pharmacophores.a zinc binding group and a Cys-reactive warhead.were designed to leverage both affinity and reactivity. A series of first-generation bifunctional inhibitors was achieved through structure-based inhibitor design. Through X-ray crystallography, engagement of both the catalytic Zn2+ and Cys165 was confirmed. A second-generation series improved on affinity by incorporating known reversible inhibitor pharmacophores; the mechanism was confirmed by exhaustive dialysis, mass spectrometry, and in vitro evaluation against the C165S mutant. Finally, a third-generation inhibitor was shown to have good cellular activity and low toxicity. In addition to our findings, an alternative method of modeling time-dependent inhibition that simplifies assay setup and allows comparison of inhibition models is discussed.

  DOI：

  10.1021/acs.jmedchem.0c01006

文献信息

• Membranes incorporating recognition moieties
  申请人：Sala Fernando Rafael

  公开号：US20050250128A1

  公开（公告）日：2005-11-10

  The present invention provides a thiosulfonate-activated ionophore comprising an ionophore, a spacer group, and an alkylthiosulfonate moiety. A preferred ionophore is gramicidin A. A preferred alkylthiosulfonate is methanethiosulfonate. The present invention also provides a conjugate comprising an ionophore, a spacer group, and a recognition molecule. Further the invention related to membranes incorporating the conjugates and biosensors comprising said membranes.

  本发明提供了一种硫代磺酸盐活化离子载体，包括离子载体、间隔基团和烷基硫代磺酸盐基团。首选离子载体是青霉素环肽A。首选的烷基硫代磺酸盐是甲烷硫代磺酸盐。本发明还提供了一种共轭物，包括离子载体、间隔基团和识别分子。此外，本发明涉及包含该共轭物的膜和包括该膜的生物传感器。
• MEMBRANES INCORPORATING RECOGNITION MOIETIES
  申请人：GENENCOR INTERNATIONAL, INC.

  公开号：EP1699420A1

  公开（公告）日：2006-09-13
• US7371585B2
  申请人：——

  公开号：US7371585B2

  公开（公告）日：2008-05-13
• [EN] MEMBRANES INCORPORATING RECOGNITION MOIETIES<br/>[FR] MEMBRANES COMPRENANT DES GROUPES FONCTIONNELS DE RECONNAISSANCE
  申请人：GENENCOR INT

  公开号：WO2005065405A1

  公开（公告）日：2005-07-21

  The present invention provides a thiosulfonate-activated ionophore comprising an ionophore, a spacer group, and an alkylthiosulfonate moiety. A preferred ionophore is gramicidin A. A preferred alkylthiosulfonate is methanethiosulfonate. The present invention also provides a conjugate comprising an ionophore, a spacer group, and a recognition molecule. Further the invention related to membranes incorporating the conjugates and biosensors comprising said membranes.