N-{2-[3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)propionylamino]-ethyl}-succinamic acid 2,5-dioxopyrrolidin-1-yl ester

• 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: N-{2-[3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)propionylamino]-ethyl}-succinamic acid 2,5-dioxopyrrolidin-1-yl ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 4-[2-[[4-(2,5-dioxopyrrolidin-1-yl)oxy-4-oxobutanoyl]amino]ethylamino]-4-oxobutanoate
• 化学式: C₁₈H₂₂N₄O₁₀
• 分子量: 454.393
• InChiKey: ZMZOBVHSPBCYSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  盐酸多柔比星 、 N-{2-[3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)propionylamino]-ethyl}-succinamic acid 2,5-dioxopyrrolidin-1-yl ester 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到N-[2-(4-(doxorubicin-3'-N-yl)-4-oxobutanoylamino)-ethyl]-succinamic acid N-hydroxysuccinimidyl ester
  参考文献：
  名称：

  Efficient One-Pot Synthesis of Doxorubicin Conjugates Through Its Amino Group to Melanotransferrin P97

  摘要：

  The amino group of doxorubicin I is reacted with bis-NHS-ester linkers 6, or anhydrides 13 to offer in high yield modified doxorubicins 7-12 and 14-16, respectively. Compounds 7-12 are mono-NHS-esters, and can be directly coupled with melanotransferrin (p97), a useful vector with the ability to cross the blood-brain barrier, to yield the expected doxorubicin-p97 conjugates. Upon activating the carboxylic group with BTTU, compound 14-16 could be used in the same reaction. Structurally, the amino group of doxorubicin is covalently bonded to the amino groups of p97. The conjugates are potential candidates for treatment of brain tumors.

  DOI：

  10.1081/scc-120021829
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-[2-(3-carboxy-propionylamino)]succinamic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-{2-[3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)propionylamino]-ethyl}-succinamic acid 2,5-dioxopyrrolidin-1-yl ester
  参考文献：
  名称：

  Protein crosslinkers, crosslinking methods and applications thereof

  摘要：

  这项披露涉及一种交联生物液体的方法，包括将生物液体与交联剂结合，以共价交联生物液体内源蛋白质形成交联凝胶。生物液体的例子包括血液、血浆或血清。

  公开号：

  US20070248567A1

文献信息

• Protein crosslinkers, crosslinking methods and applications thereof
  申请人：Pathak Chandrashekhar P.

  公开号：US20070248567A1

  公开（公告）日：2007-10-25

  Some aspects of this disclosure relate to a method for crosslinking a biological fluid comprising combining a biological fluid with a crosslinker to covalently crosslink proteins endogenous to the biological fluid to form a crosslinked gel. Examples of a biological fluid are blood, plasma, or serum.

  这项披露涉及一种交联生物液体的方法，包括将生物液体与交联剂结合，以共价交联生物液体内源蛋白质形成交联凝胶。生物液体的例子包括血液、血浆或血清。
• US9498557B2
  申请人：——

  公开号：US9498557B2

  公开（公告）日：2016-11-22
• Efficient One-Pot Synthesis of Doxorubicin Conjugates Through Its Amino Group to Melanotransferrin P97
  作者：Qingqi Chen、Damian A. Sowa、Jianlin Cai、Reinhard Gabathuler

  DOI：10.1081/scc-120021829

  日期：2003.1.8

  The amino group of doxorubicin I is reacted with bis-NHS-ester linkers 6, or anhydrides 13 to offer in high yield modified doxorubicins 7-12 and 14-16, respectively. Compounds 7-12 are mono-NHS-esters, and can be directly coupled with melanotransferrin (p97), a useful vector with the ability to cross the blood-brain barrier, to yield the expected doxorubicin-p97 conjugates. Upon activating the carboxylic group with BTTU, compound 14-16 could be used in the same reaction. Structurally, the amino group of doxorubicin is covalently bonded to the amino groups of p97. The conjugates are potential candidates for treatment of brain tumors.