N-[(2S)-6-amino-2-[[2-[(3S,9S,15S,21S)-7,13-bis(4-aminobutanoyl)-21-(4-aminobutyl)-3,9,15-tribenzyl-5,11,17,23,26-pentaoxo-19-(3-phenylpropanoyl)-1,4,7,10,13,16,19,22-octazacyclohexacos-1-yl]acetyl]amino]hexyl]-N-(2-amino-2-oxoethyl)hexadecanamide | 1478493-13-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: N-[(2S)-6-amino-2-[[2-[(3S,9S,15S,21S)-7,13-bis(4-aminobutanoyl)-21-(4-aminobutyl)-3,9,15-tribenzyl-5,11,17,23,26-pentaoxo-19-(3-phenylpropanoyl)-1,4,7,10,13,16,19,22-octazacyclohexacos-1-yl]acetyl]amino]hexyl]-N-(2-amino-2-oxoethyl)hexadecanamide
• CAS: 1478493-13-8
• 化学式: C₈₆H₁₃₃N₁₅O₁₁
• 分子量: 1553.1
• InChiKey: OGXPNLCUEXLACH-FSUNSDDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  112
• 可旋转键数：
  44
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  394
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropyl]-(4-oxo-4-prop-2-enoxybutanoyl)amino]acetic acid 、 、 、 在 1-羟基苯并三唑 、 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， 生成 N-[(2S)-6-amino-2-[[2-[(3S,9S,15S,21S)-7,13-bis(4-aminobutanoyl)-21-(4-aminobutyl)-3,9,15-tribenzyl-5,11,17,23,26-pentaoxo-19-(3-phenylpropanoyl)-1,4,7,10,13,16,19,22-octazacyclohexacos-1-yl]acetyl]amino]hexyl]-N-(2-amino-2-oxoethyl)hexadecanamide
  参考文献：
  名称：

  Lipidated Cyclic γ-AApeptides Display Both Antimicrobial and Anti-inflammatory Activity

  摘要：

  Antimicrobial peptides (AMPs) are host-defense agents capable of both bacterial membrane disruption and immunomodulation. However, the development of natural AMPs as potential therapeutics is hampered by their moderate activity and susceptibility to protease degradation. Herein we report lipidated cyclic gamma-AApeptides that have potent antibacterial activity against clinically relevant Gram-positive and Gram-negative bacteria, many of which are resistant to conventional antibiotics. We show that lipidated cyclic gamma-AApeptides mimic the bactericidal mechanism of AMPs by disrupting bacterial membranes. Interestingly, they also harness the immune response and inhibit lipopolysaccharide (LPS) activated Toll-like receptor 4 (TLR4) signaling, suggesting that lipidated cyclic gamma-AApeptides have dual roles as novel antimicrobial and anti-inflammatory agents.

  DOI：

  10.1021/cb4006613

文献信息

• Lipidated Cyclic γ-AApeptides Display Both Antimicrobial and Anti-inflammatory Activity
  作者：Yaqiong Li、Christina Smith、Haifan Wu、Shruti Padhee、Namitha Manoj、Joseph Cardiello、Qiao Qiao、Chuanhai Cao、Hang Yin、Jianfeng Cai

  DOI：10.1021/cb4006613

  日期：2014.1.17

  Antimicrobial peptides (AMPs) are host-defense agents capable of both bacterial membrane disruption and immunomodulation. However, the development of natural AMPs as potential therapeutics is hampered by their moderate activity and susceptibility to protease degradation. Herein we report lipidated cyclic gamma-AApeptides that have potent antibacterial activity against clinically relevant Gram-positive and Gram-negative bacteria, many of which are resistant to conventional antibiotics. We show that lipidated cyclic gamma-AApeptides mimic the bactericidal mechanism of AMPs by disrupting bacterial membranes. Interestingly, they also harness the immune response and inhibit lipopolysaccharide (LPS) activated Toll-like receptor 4 (TLR4) signaling, suggesting that lipidated cyclic gamma-AApeptides have dual roles as novel antimicrobial and anti-inflammatory agents.