[4-{[(4-{[(2,6-dimethylphenyl)carbamoyl]amino}phenyl)acetyl]amino}-2-(3-oxo-3-{[12-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}amino)dodecyl]amino}propyl)phenoxy]acetic acid | 1355027-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: [4-{[(4-{[(2,6-dimethylphenyl)carbamoyl]amino}phenyl)acetyl]amino}-2-(3-oxo-3-{[12-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}amino)dodecyl]amino}propyl)phenoxy]acetic acid
• 英文别名: 2-[2-[3-[12-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]dodecylamino]-3-oxopropyl]-4-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]phenoxy]acetic acid
• CAS: 1355027-67-6
• 化学式: C₅₀H₆₉N₇O₈S
• 分子量: 928.206
• InChiKey: JFTKUDHNGQQNJC-ISHCHTCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  66
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  241
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [4-({[(2,6-dimethylphenyl)amino]carbonyl}amino)phenyl]acetic acid 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 硫酸 、 palladium 10% on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 caesium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 [4-{[(4-{[(2,6-dimethylphenyl)carbamoyl]amino}phenyl)acetyl]amino}-2-(3-oxo-3-{[12-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}amino)dodecyl]amino}propyl)phenoxy]acetic acid
  参考文献：
  名称：

  LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line

  摘要：

  The tripeptide Leu-Asp-Val (LDV) is known to bind alpha(4)beta(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the alpha(4)beta(1) integrin in an adhesion assay using fluorescently labeled, alpha(4)beta(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.078

文献信息

• LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line
  作者：Estelle Gérard、Aline Meulle、Olivier Feron、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmcl.2011.10.078

  日期：2012.1

  The tripeptide Leu-Asp-Val (LDV) is known to bind alpha(4)beta(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the alpha(4)beta(1) integrin in an adhesion assay using fluorescently labeled, alpha(4)beta(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting. (C) 2011 Elsevier Ltd. All rights reserved.