indolicidin | 121798-56-9

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: indolicidin
• 英文别名: ILPWKWPWWPWRR；(2S)-2-[[(2S)-2-[[(2S)-2-[[[(2S)-1-[(2S)-2-[[(2S)-2-[[[(2S)-1-[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[[(2S)-1-[(2S)-2-[[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino]-4-methylpentanoyl]pyrrolidin-2-yl]-hydroxymethylidene]amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino]-1-hydroxyhexylidene]amino]-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]-hydroxymethylidene]amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino]-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]-hydroxymethylidene]amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino]-5-carbamimidamido-1-hydroxypentylidene]amino]-5-carbamimidamidopentanoic acid
• CAS: 121798-56-9
• 化学式: C₁₀₀H₁₃₁N₂₅O₁₄
• 分子量: 1907.3
• InChiKey: FOKROTKCEQUZRF-SLDJZXPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  139
• 可旋转键数：
  50
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  615
• 氢给体数：
  23
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  Fmoc-Pro-OH 、 Fmoc-L-亮氨酸 、 Fmoc-L-异亮氨酸 、 Fmoc-L-色氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-Pbf-L-精氨酸 在 N-甲基咪唑 、 苯甲基-2-磺酰三硝基三氮唑 、 哌啶 作用下， 以 二氯甲烷 、 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 以21%的产率得到indolicidin
  参考文献：
  名称：

  珠扩散测定法，用于发现抗微生物环肽。

  摘要：

  在光可裂解的TentaGel珠上制备了酪氨酸A和短杆菌肽S的15,536个环状十肽类似物的组合文库。将珠子在无溶剂的情况下光解，并铺在接种有细菌性草坪的琼脂平板上。在带有抗微生物活性肽（例如E18 c（kVOrnLfThiYOrnLq））的珠子周围形成了清晰的区域，该肽可抑制枯草芽孢杆菌和某些MRSA菌株的生长。

  DOI：

  10.1039/c0cc04670a

文献信息

• Identification of New Nitric Oxide-Donating Peptides with Dual Biofilm Eradication and Antibacterial Activities for Intervention of Device-Related Infections
  作者：Yue Fei、Jianbing Wu、Hong-Wei An、Kai Zhu、Bo Peng、Junquan Cai、Yihua Zhang、Li-Li Li、Hao Wang、Zhangjian Huang

  DOI：10.1021/acs.jmedchem.9b01832

  日期：2020.9.10

  Implantable medical device-related infections with biofilms have become a significant challenge in clinics. Based on the potential bacteria biofilm dispersing effect of nitric oxide (NO) and the unique antibacterial activity of antimicrobial peptides (AMP), we synthesized five peptides and selected the most potent one to conjugate its N-terminal with a furoxan moiety to offer a hitherto unknown NO-donating antimicrobial peptide (FOTyr-AMP), which exhibited Staphylococcus aureus and Escherichia coli biofilm dispersion and eradication, and potent antibacterial activities in vitro. In an implanted biofilm infection mice model, topical subcutaneous injection of FOTyr-AMP allowed synergetic eradication of bacterial biofilms and potent antibacterial activity, superior to the antibiotic cephalosporin C. Given the low hemolysis effect, little influence on the blood pressure, and potent in vivo efficacy of FOTyr-AMP, it is clear that subcutaneous administration of FOTyr-AMP could be a promising approach for the intervention of medical device-related biofilm infections with desirable safety.
• Bead diffusion assay for discovering antimicrobial cyclic peptides
  作者：Viviana S. Fluxà、Noélie Maillard、Malcolm G. P. Page、Jean-Louis Reymond

  DOI：10.1039/c0cc04670a

  日期：——

  A combinatorial library of 15,536 cyclic decapeptide analogues of tyrocidine A and gramicidin S was prepared on photocleavable TentaGel beads. The beads were photolyzed without solvent, and spread onto an agar plate inoculated with bacterial lawn. Clear zones were formed around beads carrying antimicrobially active peptides such as E18 c(kVOrnLfThiYOrnLq), which inhibited growth of B. subtilis and

  在光可裂解的TentaGel珠上制备了酪氨酸A和短杆菌肽S的15,536个环状十肽类似物的组合文库。将珠子在无溶剂的情况下光解，并铺在接种有细菌性草坪的琼脂平板上。在带有抗微生物活性肽（例如E18 c（kVOrnLfThiYOrnLq））的珠子周围形成了清晰的区域，该肽可抑制枯草芽孢杆菌和某些MRSA菌株的生长。