YSAYPDSVPMMS[Nε-(5-hexynoyl)lysine]-PTX | 1246194-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: YSAYPDSVPMMS[Nε-(5-hexynoyl)lysine]-PTX
• 英文别名: (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxypropanoyl]amino]-6-[4-[1-[6-[2-[2-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-2-oxoethoxy]acetyl]oxyhexyl]triazol-4-yl]butanoylamino]hexanoic acid
• CAS: 1246194-69-3
• 化学式: C₁₂₈H₁₇₀N₁₈O₄₀S₂
• 分子量: 2664.99
• InChiKey: RIYHTJRLFKFNBR-UHUMTRIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  188
• 可旋转键数：
  76
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  907
• 氢给体数：
  22
• 氢受体数：
  45

反应信息

• 作为产物：
  描述：

  2'-[2-(2-(6-azidohexyloxy)-2-oxoethoxy)acetyl]-O-paclitaxel 、 YSAYPDSVPMMS[Nε-(5-hexynoyl)lysine] 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以65%的产率得到YSAYPDSVPMMS[Nε-(5-hexynoyl)lysine]-PTX
  参考文献：
  名称：

  Novel Targeted System To Deliver Chemotherapeutic Drugs to EphA2-Expressing Cancer Cells

  摘要：

  The efficacy of anticancer drugs is often limited by their systemic toxicities and adverse side effects. We report that the EphA2 receptor is overexpressed preferentially in several human cancer cell lines compared to normal tissues and that an EphA2 targeting peptide (YSAYPDSVPMMS) can be effective in delivering anticancer agents to such tumors. Hence, we report on the synthesis and characterizations of a novel EphA2-targeting agent conjugated with the chemotherapeutic drug paclitaxel. We found that the peptide-drug conjugate is dramatically more effective than paclitaxel alone at inhibiting tumor growth in a prostate cancer xenograft model, delivering significantly higher levels of drug to the tumor site. We believe these studies open the way to the development of a new class of therapeutic compounds that exploit the EphA2 receptor for drug delivery to cancer cells.

  DOI：

  10.1021/jm201743s