| 1384215-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 1384215-71-7
• 化学式: C₂₀H₂₄N₄O₈S
• 分子量: 480.499
• InChiKey: KLGHDVCWXAZTIQ-RFHHWMCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  196.2
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 谷胱甘肽 在 盐酸 、 乙二胺四乙酸 作用下， 以 aq. phosphate buffer 为溶剂， 生成
  参考文献：
  名称：

  An Arsenical–Maleimide for the Generation of New Targeted Biochemical Reagents

  摘要：

  The finding that arsenic trioxide is an effective treatment for acute promyelocytic leukemia has renewed interest in the pharmacological uses of inorganic and organic arsenicals. Here we synthesized and characterized the reactivity of an arsenical-maleimide (As-Mal) that can be efficiently conjugated to exposed cysteine residues in peptides and proteins with the ultimate goal of directing these As(III) species to vicinal thiols in susceptible targets within cells and tissues. As-Mal conjugated to a surface cysteine in thioredoxin provides a more potent inhibitor for Escherichia coli thioredoxin reductase than comparable simple inorganic or organic arsenicals. As-Mal can be coupled to all of the eight cysteine residues of reduced unfolded ribonuclease A or to site-specific locations using appropriate cysteine mutations. We observed particularly strong binding to the two CxxC motifs of protein disulfide isomerase using a mutant RNase in which As-Mal was specifically incorporated at residues 26 and 110. As-Mal will serve as a facile reagent for the incorporation of As(III) species into a wide range of thiol-containing proteins, biomaterials, and surfaces.

  DOI：

  10.1021/ja310553h

文献信息

• Manipulation of Glutathione-Mediated Degradation of Thiol–Maleimide Conjugates
  作者：Haocheng Wu、Paige J. LeValley、Tianzhi Luo、April M. Kloxin、Kristi L. Kiick

  DOI：10.1021/acs.bioconjchem.8b00546

  日期：2018.11.21

  effects, electron-withdrawing capacity of the N-substituted moiety, as well as the potential for intramolecular catalytic hydrogen bonding of amine substituents with water (particularly in the case of ring opening). Further model studies of 4-mercaptohydrocinnamic acid (MPP, pKa 7.0) and N-acetyl-l-cysteine (NAC, pKa 9.5) conjugated to selected N-substituted maleimides and then incubated with glutathione

  响应于含硫醇的环境，硫醚琥珀酰亚胺点击键的复古迈克尔型加成和硫醇交换为设计可控药物递送的谷胱甘肽敏感的可降解水凝胶提供了一种新颖的策略。在这里我们表征了动力学和逆向迈克尔型加成和硫醇交换程度与硫醇的p K a和马来酰亚胺的N-取代基的身份的变化。通过典型的迈克尔型加成制备了一系列的N-取代的硫醚琥珀酰亚胺。结合到N-乙基马来酰亚胺（NEM），N-苯基马来酰亚胺（NPM）上的4-巯基苯乙酸（MPA，p K a 6.6）的模型研究（1 H NMR，HPLC）或N-氨乙基马来酰亚胺（NAEM），然后与谷胱甘肽一起孵育，显示半衰期为3.1到18 h，转化率约为12％到90％。交换速率和水解开环速率的变化似乎是由共振效应，N-取代的部分的吸电子能力以及胺取代基与水的分子内催化氢键合的电势引起的（尤其是在这种情况下）开环）。4-巯基肉桂酸（MPP，p K a 7.0）和N-乙酰基-1-半胱氨酸（NAC，p
• Development of novel linkers to conjugate pharmacophores to a carrier antibody
  作者：Moorthy S.S. Palanki、Abhijit Bhat、Rodney W. Lappe、Bin Liu、Bryan Oates、John Rizzo、Nebojsa Stankovic、Curt Bradshaw

  DOI：10.1016/j.bmcl.2012.05.040

  日期：2012.7

  We have developed modified maleimide novel linkers with improved chemical stability that could potentially be used in conjugating various pharmacophores such as oligo nucleotides, peptides, and proteins to antibodies to afford novel biologics with well-defined therapeutic benefits and improved pharmacokinetic properties. These linkers expand the array of tools available for bioconjugation of pharmacophores to antibodies. (C) 2012 Elsevier Ltd. All rights reserved.