Tyr-c(S-CH2-S)-[D-Cys-Phe-2-Nal-Cys]-NH2 | 1192224-08-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Tyr-c(S-CH2-S)-[D-Cys-Phe-2-Nal-Cys]-NH2
• 英文别名: (5R,8S,11S,14S)-14-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-11-benzyl-8-(naphthalen-2-ylmethyl)-7,10,13-trioxo-1,3-dithia-6,9,12-triazacyclopentadecane-5-carboxamide；(5R,8S,11S,14S)-14-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-11-benzyl-8-(naphthalen-2-ylmethyl)-7,10,13-trioxo-1,3-dithia-6,9,12-triazacyclopentadecane-5-carboxamide
• CAS: 1192224-08-0
• 化学式: C₃₈H₄₂N₆O₆S₂
• 分子量: 742.92
• InChiKey: FWDMWCQXNFZSCZ-PMUGGPHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Tyr-D-Cys-Phe-2-Nal-Cys-NH2 、 二溴甲烷 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Tyr-c(S-CH2-S)-[D-Cys-Phe-2-Nal-Cys]-NH2
  参考文献：
  名称：

  Pentapeptides Displaying μ Opioid Receptor Agonist and δ Opioid Receptor Partial Agonist/Antagonist Properties

  摘要：

  Chronic use of mu-opioid agonists has been shown to cause neurochemical adaptations resulting in tolerance and dependence, While the analgesic effects of these drugs are mediated by mu-opioid receptors (MOR), several studies have shown that antagonism or knockdown of delta-opioid receptors (DOR) can lessen or prevent development of tolerance and dependence. On the basis of computational modeling of putative active and inactive conformations of MOR and DOR, we have synthesized a series of pentapeptides with the goal of developing a MOR agonist/DOR antagonist peptide with similar affinity at both receptors as a tool to probe functional opioid receptor interaction(s). The eight resulting naphthylalanine-substituted cyclic pentapeptides displayed variable mixed-efficacy profiles. The most promising peptide (9; Tyr-c(S-CH2-S)[D-Cys-Phe-2-Nal-Cys]NH2) displayed it MOR agonist and DOR partial agonist/antagonist profile and bound with equipotent affinity (K-i similar to 0.5 nM) to both receptors, but also Showed K opioid receptor (KOR) agonist activity.

  DOI：

  10.1021/jm9007483