苄氧羰基-甘氨酰-甘氨酰-组氨酸 | 52396-73-3

• 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
• 中文名称: 苄氧羰基-甘氨酰-甘氨酰-组氨酸
• 英文名称: Z-glycyl-glycyl-L-histidine
• 英文别名: Benzyloxycarbonylglycylglycyl-L-histidin；N-benzyloxycarbonyl-glycyl->-glycyl->-histidine；Z-Gly-gly-his-OH；(2S)-3-(1H-imidazol-5-yl)-2-[[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetyl]amino]propanoic acid
• CAS: 52396-73-3
• 化学式: C₁₈H₂₁N₅O₆
• 分子量: 403.395
• InChiKey: PWNQBHDTOAIVDG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄氧羰基-甘氨酰-甘氨酰-组氨酸 在 氢溴酸 、 1-羟基苯并三唑 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 反应 1.25h， 生成 1,4-bis((2-((glycyl-glycyl-L-histidyl)amino)ethyl)amino)-5,8-dihydroxyanthracene-9,10-dione dibromohydrate
  参考文献：
  名称：

  Synthesis and antitumor properties of an anthraquinone bisubstituted by the copper chelating peptide Gly-Gly-L-His

  摘要：

  A new molecule 4 [(GGH-DAE)2DHQ] associating the 1,4,5,8-tetrahydroxyanthraquinone ring (DHQ) of the antitumor drug mitoxantrone (2), two diaminoethylene chains (DAE), and the metal-chelating peptide Gly-Gly-His (GGH) has been synthesized. Such a molecule presents characteristics able to induce antitumor activity: compound 4 intercalates into DNA as measured by DELTAT(m), fluorescence quenching, and viscometry; ESR studies demonstrate that several types of Cu complexes are formed depending on PH; and the production of free radicals, as evidenced by spin-trapping, is enhanced by 4. In vitro, in leukemia cells L1210 and mammary cells MCF7, 4 is slightly less cytostatic than mitoxantrone, but substantially less toxic. In vivo, in leukemia P388 on mice, a T/C value of 230 is obtained at 25 mg/kg, higher than the one of mitoxantrone, which is toxic at the same dose.

  DOI：

  10.1021/jm00067a005
• 作为产物：
  描述：

  l-histidine methyl ester dihydrochloride 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 苄氧羰基-甘氨酰-甘氨酰-组氨酸
  参考文献：
  名称：

  Synthesis and antitumor properties of an anthraquinone bisubstituted by the copper chelating peptide Gly-Gly-L-His

  摘要：

  A new molecule 4 [(GGH-DAE)2DHQ] associating the 1,4,5,8-tetrahydroxyanthraquinone ring (DHQ) of the antitumor drug mitoxantrone (2), two diaminoethylene chains (DAE), and the metal-chelating peptide Gly-Gly-His (GGH) has been synthesized. Such a molecule presents characteristics able to induce antitumor activity: compound 4 intercalates into DNA as measured by DELTAT(m), fluorescence quenching, and viscometry; ESR studies demonstrate that several types of Cu complexes are formed depending on PH; and the production of free radicals, as evidenced by spin-trapping, is enhanced by 4. In vitro, in leukemia cells L1210 and mammary cells MCF7, 4 is slightly less cytostatic than mitoxantrone, but substantially less toxic. In vivo, in leukemia P388 on mice, a T/C value of 230 is obtained at 25 mg/kg, higher than the one of mitoxantrone, which is toxic at the same dose.

  DOI：

  10.1021/jm00067a005

文献信息

• Composition containing a penem or carbapenem antibiotic
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0226304B1

  公开（公告）日：1991-08-28
• Catalytic Inactivation of Human Carbonic Anhydrase I by a Metallopeptide−Sulfonamide Conjugate is Mediated by Oxidation of Active Site Residues
  作者：Nikhil H. Gokhale、Seth Bradford、J. A. Cowan

  DOI：10.1021/ja0778038

  日期：2008.2.1

  Oxidation of active site residues (His and Trp), following catalytic inactivation of human carbonic anhydrase I by a copper-ATCUN conjugate of sulfanilimide, is evidenced by mass spectrometric analysis of tryptic and chymotryptic digest of the modified CA-I. Accordingly, residue oxidation rather than protein cleavage is the demonstrated mods of inactivation. An apparent second-order rate constant, k(2) similar to 7600 M(-1)min(-1), has been determined for catalytic inactivation of CA-I.
• US4757066A
  申请人：——

  公开号：US4757066A

  公开（公告）日：1988-07-12