4-((3,5-bis((2,3-dihydroxypropyl)aminoformyl)-2,4,6-triiodophenyl)amino)-4-oxobutanoic acid | 188655-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((3,5-bis((2,3-dihydroxypropyl)aminoformyl)-2,4,6-triiodophenyl)amino)-4-oxobutanoic acid
• 英文别名: N-[3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodo-phenyl]-succinamic acid；4-[3,5-Bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-4-oxobutanoic acid
• CAS: 188655-32-5
• 化学式: C₁₈H₂₂I₃N₃O₉
• 分子量: 805.101
• InChiKey: GFLLKEKBVGHHKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  205.52
• 氢给体数：
  8.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-((3,5-bis((2,3-dihydroxypropyl)aminoformyl)-2,4,6-triiodophenyl)amino)-4-oxobutanoic acid 在 silica gel 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 {3-[3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodo-phenylcarbamoyl]-propionylamino}acetic acid
  参考文献：
  名称：

  Starch microspheres as carriers for X-ray imaging contrast agents: Synthesis and stability of new amino-acid linker derivatives

  摘要：

  The relative stability of particulate contrast agents for X-ray imaging, consisting of a succinic-acid derivative of a water-soluble X-ray contrast agent bound to starch particles through an amino-acid ester bond, has been studied. To investigate the effect of chain length of the amino-acid Linker on degradation rate, two glycine-linked derivatives and a corresponding beta-alanine-linked derivative were prepared as model compounds. The cleavage rate of the amino-acid ester bond in the starch particle beta-alanine derivative had a significantly lower cleavage rate than in the corresponding glycine derivatives; after 22 h in human blood serum at 37 degrees C the remaining fraction of the undegraded beta-alanine-linked derivative was 78%, while 31.1 and 29.3% were the remaining fractions of the two glycine-linked derivatives. The cleavage data correlated well with biphasic cleavage processes with two distinct half lives for the respective pseudo first order processes. The second preparation with the glycine linker had a cleavage profile and rate equivalent to that of the first one in human blood serum, but the corresponding hydrolysis in phosphate buffer was significantly slower with 79.9%-remaining fraction after 22 h, and was apparently a monophasic pseudo first order reaction. Variation of the degradability of the starch matrix had apparently no significant effect on the cleavage rates of the linker. This suggests that components in the human blood serum catalyze the cleavage of the ester bond in these derivatives and that a fraction of the covalently bound contrast agent had a significantly slower cleavage rate from the matrix. The derivative with a glycine linker between the carrier matrix and the contrast agent is a promising candidate for liver and spleen directed X-ray contrast with respect to density of contrast generating iodine and biodegradability. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00286-8
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以62.9 g的产率得到4-((3,5-bis((2,3-dihydroxypropyl)aminoformyl)-2,4,6-triiodophenyl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  Starch microspheres as carriers for X-ray imaging contrast agents: Synthesis and stability of new amino-acid linker derivatives

  摘要：

  The relative stability of particulate contrast agents for X-ray imaging, consisting of a succinic-acid derivative of a water-soluble X-ray contrast agent bound to starch particles through an amino-acid ester bond, has been studied. To investigate the effect of chain length of the amino-acid Linker on degradation rate, two glycine-linked derivatives and a corresponding beta-alanine-linked derivative were prepared as model compounds. The cleavage rate of the amino-acid ester bond in the starch particle beta-alanine derivative had a significantly lower cleavage rate than in the corresponding glycine derivatives; after 22 h in human blood serum at 37 degrees C the remaining fraction of the undegraded beta-alanine-linked derivative was 78%, while 31.1 and 29.3% were the remaining fractions of the two glycine-linked derivatives. The cleavage data correlated well with biphasic cleavage processes with two distinct half lives for the respective pseudo first order processes. The second preparation with the glycine linker had a cleavage profile and rate equivalent to that of the first one in human blood serum, but the corresponding hydrolysis in phosphate buffer was significantly slower with 79.9%-remaining fraction after 22 h, and was apparently a monophasic pseudo first order reaction. Variation of the degradability of the starch matrix had apparently no significant effect on the cleavage rates of the linker. This suggests that components in the human blood serum catalyze the cleavage of the ester bond in these derivatives and that a fraction of the covalently bound contrast agent had a significantly slower cleavage rate from the matrix. The derivative with a glycine linker between the carrier matrix and the contrast agent is a promising candidate for liver and spleen directed X-ray contrast with respect to density of contrast generating iodine and biodegradability. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00286-8

文献信息

• REACTIVE MULTI-ARM POLYMERS HAVING BRANCHED END GROUPS
  申请人：Boston Scientific Scimed Inc.

  公开号：US20210060183A1

  公开（公告）日：2021-03-04

  In some aspects, the present disclosure pertains to a polymer that comprises a plurality of polymer arms, wherein a first portion of the polymer arms comprise a reactive end group and wherein a second portion of the polymer arms comprise a branched end group that comprise a plurality of covalently attached diagnostic and/or therapeutic groups, which may be, for example, radiocontrast groups or radioactive groups. Other aspects pertain to a system that comprises (a) a first composition comprising such a polymer and (b) a second composition comprising a multifunctional compound that comprises reactive functional groups that are reactive with the reactive end group of the multi-arm polymer. Still other aspects pertain to a crosslinked reaction product of (a) such a polymer and (b) a multifunctional compound that comprises functional groups that are reactive with the reactive end group of the multi-arm polymer.

  在某些方面，本公开涉及一种聚合物，其包括多个聚合物臂，其中聚合物臂的第一部分包括反应性末端基团，聚合物臂的第二部分包括分支末端基团，该分支末端基团包括多个共价连接的诊断和/或治疗基团，例如放射对比剂或放射性基团。其他方面涉及一种系统，该系统包括（a）包含这种聚合物的第一组成份和（b）包含具有与多臂聚合物的反应性末端基团反应的反应性功能基团的多功能化合物的第二组成份。还有其他方面涉及（a）这种聚合物和（b）包含与多臂聚合物的反应性末端基团反应的功能性基团的多功能化合物的交联反应产物。
• [EN] REACTIVE MULTI-ARM POLYMERS HAVING BRANCHED END GROUPS<br/>[FR] POLYMÈRES À PLUSIEURS BRAS RÉACTIFS AYANT DES GROUPES TERMINAUX RAMIFIÉS
  申请人：BOSTON SCIENT SCIMED INC

  公开号：WO2021041234A1

  公开（公告）日：2021-03-04

  In some aspects, the present disclosure pertains to a polymer that comprises a plurality of polymer arms, wherein a first portion of the polymer arms comprise a reactive end group and wherein a second portion of the polymer arms comprise a branched end group that comprise a plurality of covalently attached diagnostic and/or therapeutic groups, which may be, for example, radiocontrast groups or radioactive groups. Other aspects pertain to a system that comprises (a) a first composition comprising such a polymer and (b) a second composition comprising a multifunctional compound that comprises reactive functional groups that are reactive with the reactive end group of the multi-arm polymer. Still other aspects pertain to a crosslinked reaction product of (a) such a polymer and (b) a multifunctional compound that comprises functional groups that are reactive with the reactive end group of the multi-arm polymer.