Mal-amido-(CH2COOH)2 | 207613-14-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Mal-amido-(CH2COOH)2
• 英文别名: 2-[carboxymethyl-[3-(2,5-dioxopyrrol-1-yl)propanoyl]amino]acetic acid
• CAS: 207613-14-7
• 化学式: C₁₁H₁₂N₂O₇
• 分子量: 284.225
• InChiKey: WGKBLBPWMDGTDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-氨基-3-苯基丙酰胺基)-N-(4-(羟甲基)苯基)-6-(((4-甲氧基苯基)二苯基甲基)氨基)己酰胺 、 Mal-amido-(CH2COOH)2 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 生成
  参考文献：
  名称：

  Doxorubicin immunoconjugates containing bivalent, lysosomally-Cleavable dipeptide linkages

  摘要：

  Bivalent doxorubicin (DOX)-dipeptides (16a-c) were prepared and conjugated to the monoclonal antibody BR96. The dipeptides are cleaved by lysosomal proteases following internalization of the resulting immunoconjugates. Conjugate 18b demonstrated antigen-specific in vitro tumor cell killing activity (IC50 = 0.2 muM) that was equipotent to DOX with a near doubling of drug molecules/MAb. Size exclusion chromatography showed 18b to be a noncovalent dimer that was formed immediately upon conjugation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00194-4
• 作为产物：
  描述：

  3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoyl chloride 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Mal-amido-(CH2COOH)2
  参考文献：
  名称：

  Doxorubicin immunoconjugates containing bivalent, lysosomally-Cleavable dipeptide linkages

  摘要：

  Bivalent doxorubicin (DOX)-dipeptides (16a-c) were prepared and conjugated to the monoclonal antibody BR96. The dipeptides are cleaved by lysosomal proteases following internalization of the resulting immunoconjugates. Conjugate 18b demonstrated antigen-specific in vitro tumor cell killing activity (IC50 = 0.2 muM) that was equipotent to DOX with a near doubling of drug molecules/MAb. Size exclusion chromatography showed 18b to be a noncovalent dimer that was formed immediately upon conjugation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00194-4

文献信息

• Doxorubicin immunoconjugates containing bivalent, lysosomally-Cleavable dipeptide linkages
  作者：Gene M Dubowchik、Shilpa Radia、Harold Mastalerz、Michael A Walker、Raymond A Firestone、H Dalton King、Sandra J Hofstead、David Willner、Shirley J Lasch、Pamela A Trail

  DOI：10.1016/s0960-894x(02)00194-4

  日期：2002.6

  Bivalent doxorubicin (DOX)-dipeptides (16a-c) were prepared and conjugated to the monoclonal antibody BR96. The dipeptides are cleaved by lysosomal proteases following internalization of the resulting immunoconjugates. Conjugate 18b demonstrated antigen-specific in vitro tumor cell killing activity (IC50 = 0.2 muM) that was equipotent to DOX with a near doubling of drug molecules/MAb. Size exclusion chromatography showed 18b to be a noncovalent dimer that was formed immediately upon conjugation. (C) 2002 Elsevier Science Ltd. All rights reserved.