[(2S,5S,8R,11S,14S,17S)-17-(4-Amino-butyl)-8-benzyl-11-(3-guanidino-propyl)-5-(1H-imidazol-2-ylmethyl)-14-(1H-indol-3-ylmethyl)-3,6,9,12,15,18-hexaoxo-1-tetradecanoyl-1,4,7,10,13,16-hexaaza-cyclooctadec-2-yl]-acetic acid | 137668-66-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: [(2S,5S,8R,11S,14S,17S)-17-(4-Amino-butyl)-8-benzyl-11-(3-guanidino-propyl)-5-(1H-imidazol-2-ylmethyl)-14-(1H-indol-3-ylmethyl)-3,6,9,12,15,18-hexaoxo-1-tetradecanoyl-1,4,7,10,13,16-hexaaza-cyclooctadec-2-yl]-acetic acid
• CAS: 137668-66-7
• 化学式: C₅₆H₈₁N₁₃O₉
• 分子量: 1080.34
• InChiKey: KSFRBPXVXPHHQB-HKLLWPEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  78.0
• 可旋转键数：
  28.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  352.57
• 氢给体数：
  12.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 NAlpha-BOC-Nε-FMOC-L-赖氨酸 、 Boc-D-苯丙氨酸 、 N-叔丁氧羰基-N'-醛基-L-色氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 p-benzhydrylamine resin 作用下， 生成 [(2S,5S,8R,11S,14S,17S)-17-(4-Amino-butyl)-8-benzyl-11-(3-guanidino-propyl)-5-(1H-imidazol-2-ylmethyl)-14-(1H-indol-3-ylmethyl)-3,6,9,12,15,18-hexaoxo-1-tetradecanoyl-1,4,7,10,13,16-hexaaza-cyclooctadec-2-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and biological activities of fatty acid conjugates of a cyclic lactam .alpha.-melanotropin

  摘要：

  Four fatty acid conjugates of a cyclic lactam-bridged alpha-MSH fragment analogue were synthesized and their potencies and biological activities compared in several melanotropin bioassays. Palmitoyl, myristoyl, decanoyl, and hexanoyl conjugates of H-Asp-HiS-D-Phe-Arg-Trp-Lys-NH2 were prepared. In the in vitro mouse melanoma cell assay, each of the conjugates was 10-100 times more potent than alpha-MSH or the substrate peptide in elevating tyrosinase activity. The shorter conjugates of hexanoic and decanoic acid were as potent as alpha-MSH in the lizard skin bioassay, whereas the longer myristoyl and palmitoyl analogues were about 100 times less potent. The potency of the myristoyl and palmitoyl conjugates increased with time in contact with the skins. These observations may be related to the more lipid-like nature of these peptide-fatty acid conjugates. Each of the conjugates exhibited prolonged melanotropic activity in the lizard skin bioassays and in the mouse S91 melanoma tyrosinase bioassay, since the biological response continued following removal of the conjugates from the incubation media. The prolonged residual melanotropic activity resulted from conjugation of the fatty acids to the MSH fragment analogue since the analogue itself did not exhibit prolonged activity.

  DOI：

  10.1021/jm00079a015