methyl 2-(5-(1,2-dithiolan-3-yl)pentanamido)-3-(1H-imidazol-4-yl)propanoate | 1268673-50-2

• 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
• 英文名称: methyl 2-(5-(1,2-dithiolan-3-yl)pentanamido)-3-(1H-imidazol-4-yl)propanoate
• 英文别名: methyl (2S)-2-[5-(dithiolan-3-yl)pentanoylamino]-3-(1H-imidazol-5-yl)propanoate
• CAS: 1268673-50-2
• 化学式: C₁₅H₂₃N₃O₃S₂
• 分子量: 357.498
• InChiKey: DSABMAZYQFYQSP-ABLWVSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  l-histidine methyl ester dihydrochloride 、 Thioctic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 异丁酰胺 为溶剂， 以65%的产率得到methyl 2-(5-(1,2-dithiolan-3-yl)pentanamido)-3-(1H-imidazol-4-yl)propanoate
  参考文献：
  名称：

  Carbonic Anhydrase Activators: Gold Nanoparticles Coated with Derivatized Histamine, Histidine, and Carnosine Show Enhanced Activatory Effects on Several Mammalian Isoforms

  摘要：

  Lipoic acid moieties were attached to amine or amino acids showing activating properties against the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). The obtained lipoic acid conjugates of histamine, L-histidine methyl ester, and L-carnosine methyl ester were attached to gold nanoparticles (NPs) by reaction with Au(III) salts in reducing conditions. The CA activators (CAAs) coated NPs showed low nanomolar activation (K(A)s of 1-9 nM) of relevant cytosolic, membrane-bound, mitochondrial, and transmembrane CA isoforms, such as CA I, II, IV, VA, VII, and XIV. These NPs also effectively activated CAs ex vivo., in whole blood experiments, with an increase of 200-280% of the CA activity. This is the first example of enzyme activation with nanoparticles and may lead to biomedical applications for condition in which the CA activity is diminished, such as aging, Alzheimer's disease, or CA deficiency syndrome.

  DOI：

  10.1021/jm101284a

文献信息

• Carbonic Anhydrase Activators: Gold Nanoparticles Coated with Derivatized Histamine, Histidine, and Carnosine Show Enhanced Activatory Effects on Several Mammalian Isoforms
  作者：Mohamed-Chiheb Saada、Jean-Louis Montero、Daniela Vullo、Andrea Scozzafava、Jean-Yves Winum、Claudiu T. Supuran

  DOI：10.1021/jm101284a

  日期：2011.3.10

  Lipoic acid moieties were attached to amine or amino acids showing activating properties against the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). The obtained lipoic acid conjugates of histamine, L-histidine methyl ester, and L-carnosine methyl ester were attached to gold nanoparticles (NPs) by reaction with Au(III) salts in reducing conditions. The CA activators (CAAs) coated NPs showed low nanomolar activation (K(A)s of 1-9 nM) of relevant cytosolic, membrane-bound, mitochondrial, and transmembrane CA isoforms, such as CA I, II, IV, VA, VII, and XIV. These NPs also effectively activated CAs ex vivo., in whole blood experiments, with an increase of 200-280% of the CA activity. This is the first example of enzyme activation with nanoparticles and may lead to biomedical applications for condition in which the CA activity is diminished, such as aging, Alzheimer's disease, or CA deficiency syndrome.