LKLFKKILKVL-NH2 | 898528-99-9

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: LKLFKKILKVL-NH2
• 英文别名: BP33；H-Leu-Lys-Leu-Phe-Lys-Lys-Ile-Leu-Lys-Val-Leu-NH2；(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-amino-4-methylpentanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-N-[(2S,3S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]hexanamide
• CAS: 898528-99-9
• 化学式: C₆₈H₁₂₄N₁₆O₁₁
• 分子量: 1341.83
• InChiKey: NLADUGFMICSPKM-TZMVSQBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  95
• 可旋转键数：
  50
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  Rink amide resin 、 Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-异亮氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 2-肟氰乙酸乙酯 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.2h， 生成 LKLFKKILKVL-NH2
  参考文献：
  名称：

  Cell-penetrating γ-peptide/antimicrobial undecapeptide conjugates with anticancer activity

  摘要：

  In this study, we combined a cell-penetrating gamma-peptide, PEG-1, with antimicrobial undecapeptides in order to provide compounds with anticancer properties against MDA-MB-231 human breast cancer cells. We demonstrated that the conjugates were more cytotoxic than Ac-PEG-1 and the parent undecapeptides. We also evaluated the toxicity of the conjugates against non-malignant cells. The peptide conjugate with the best biological profile was BP77-PEG-1, which, at 10 mu M, showed a 71% growth inhibition in MDA-MB-231 cells and only a 17% inhibition in non-malignant cells. Therefore, this study suggests that PEG-1 mediated the undecapeptide delivery into cancer cells and that these conjugates are the proof-of-concept of this strategy to generate improved anticancer drugs based on peptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.003

文献信息

• Cell-penetrating γ-peptide/antimicrobial undecapeptide conjugates with anticancer activity
  作者：Cristina Rosés、Daniel Carbajo、Glòria Sanclimens、Josep Farrera-Sinfreu、Adriana Blancafort、Glòria Oliveras、Anna D. Cirac、Eduard Bardají、Teresa Puig、Marta Planas、Lidia Feliu、Fernando Albericio、Miriam Royo

  DOI：10.1016/j.tet.2012.02.003

  日期：2012.6

  In this study, we combined a cell-penetrating gamma-peptide, PEG-1, with antimicrobial undecapeptides in order to provide compounds with anticancer properties against MDA-MB-231 human breast cancer cells. We demonstrated that the conjugates were more cytotoxic than Ac-PEG-1 and the parent undecapeptides. We also evaluated the toxicity of the conjugates against non-malignant cells. The peptide conjugate with the best biological profile was BP77-PEG-1, which, at 10 mu M, showed a 71% growth inhibition in MDA-MB-231 cells and only a 17% inhibition in non-malignant cells. Therefore, this study suggests that PEG-1 mediated the undecapeptide delivery into cancer cells and that these conjugates are the proof-of-concept of this strategy to generate improved anticancer drugs based on peptides. (C) 2012 Elsevier Ltd. All rights reserved.