c(Leu-Lys-Leu-Lys-Lys-Phe-Leu-Lys-Lys-Gln) | 943342-95-8

• 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: c(Leu-Lys-Leu-Lys-Lys-Phe-Leu-Lys-Lys-Gln)
• 英文别名: BPC144；cyclo[Gln-Leu-Lys-Leu-Lys-Lys-Phe-Leu-Lys-Lys]；3-[(2S,5S,8S,11S,14S,17S,20S,23S,26S,29S)-8,14,17,26,29-pentakis(4-aminobutyl)-20-benzyl-5,11,23-tris(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30-decaoxo-1,4,7,10,13,16,19,22,25,28-decazacyclotriacont-2-yl]propanamide
• CAS: 943342-95-8
• 化学式: C₆₂H₁₁₀N₁₆O₁₁
• 分子量: 1255.66
• InChiKey: YDWIWGYPTDBSMV-RJEWGMQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  89
• 可旋转键数：
  31
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  464
• 氢给体数：
  16
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  cyclo[Gln-Lys-Lys-Lys-Lys-Lys-Phe-Lys-Lys-Leu] 在 水 、 三氟乙酸 作用下， 反应 1.0h， 生成 c(Leu-Lys-Leu-Lys-Lys-Phe-Leu-Lys-Lys-Gln)
  参考文献：
  名称：

  Antimicrobial cyclic decapeptides with anticancer activity

  摘要：

  Antimicrobial peptides have been considered as potential candidates for cancer therapy We report here the cytotoxicity of a library of 66 antibacterial cyclodecapeptides on human carcinoma cell lines and their effects on apoptosis [as assessed by cleavage of poly(ADP-ribose) polymerase (PARP)] and cell signaling proteins (p53 and ERK1/2) in cultured human cervical carcinoma cells A design of experiments approach permitted to analyze the results of a subset of 16 peptides and define rules for high anticancer activity against MDA-MB-231 breast carcinoma cells Eight peptides were identified with IC50 values ranging from 18 5 to 57 5 mu M against the five cell lines tested being HeLa cells the most sensitive Among these sequences BPC88 BPC96 BPC98 and BPC194 displayed specificity and high cytotoxicity against HeLa cells (IC50 of 22 5-385 mu M) showed low hemolytic activity and low cytotoxicity to non-malignant fibroblasts and were stable to proteases in human serum Induction of apoptosis by these peptides was observed and the apoptotic effect of BPC88 and BPC96 caused a marked decrease on the activated form of ERK1/2 kinase and an induction of p53 We further showed that BPC96 at low doses synergized the cytotoxic effect of cisplatin These findings suggest that cyclic decapeptides may represent novel anticancer agents providing a new strategy in cancer therapy (C) 2010 Elsevier Inc All rights reserved

  DOI：

  10.1016/j.peptides.2010.07.027