Ac(CAFIM) | 460325-16-0

• 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: Ac(CAFIM)
• 英文别名: Ac-Cys(1)-Ala-Phe-Ile-Met-(1)；N-[(3S,6S,9S,12S,15R)-9-benzyl-6-[(2S)-butan-2-yl]-12-methyl-3-(2-methylsulfanylethyl)-2,5,8,11,14-pentaoxo-1-thia-4,7,10,13-tetrazacyclohexadec-15-yl]acetamide
• CAS: 460325-16-0
• 化学式: C₂₈H₄₁N₅O₆S₂
• 分子量: 607.795
• InChiKey: IOIXQYBEGXEBIV-XYNXPQAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  213
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 盐酸胍 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 2.0h， 生成 Ac(CAFIM)
  参考文献：
  名称：

  Highly Potent Inhibitors of Quorum Sensing in Staphylococcus aureus Revealed Through a Systematic Synthetic Study of the Group-III Autoinducing Peptide

  摘要：

  Methods to intercept bacterial quorum sensing (QS) have attracted significant attention as potential anti-infective therapies. Staphylococcus aureus is a major human pathogen that utilizes autoinducing peptide (AIP) signals to mediate QS and thereby regulate virulence. S. aureus strains are categorized into four groups (I-IV) according to their AIP signal and cognate extracellular receptor, AgrC. Each group is associated with a certain disease profile, and S. aureus group Ill strains are responsible for toxic shock syndrome and have been underestimated in other infections to date. A limited set of non-native AIP analogs have been shown to inhibit AgrC receptors; such compounds represent promising tools to study QS pathways in S. aureus. We seek to expand this set of chemical probes and report herein the first design, synthesis, and biological testing of AIP-III mimetics. A set of non-native peptides was identified that can inhibit all four of the AgrC receptors (I-IV) with picomolar IC50 values in reporter strains These analogs also blocked hemolysis by wild type S. aureus group I-IV strains-a virulence trait under the control of QS-at picomolar concentrations Moreover, four of the lead AgrC inhibitors were capable of attenuating the production of toxic shock syndrome toxin -1 (also under the control of QS) by over 80% at nanomolar concentrations in a wild type S. aureus group Ill strain. These peptides represent, to our knowledge, the most potent synthetic inhibitors of QS in S. aureus known, and constitute new and readily accessible chemical tools for the study of the AgrC system and virulence in this deadly pathogen.

  DOI：

  10.1021/ja3112115

文献信息

• US20140256615A1
  申请人：——

  公开号：US20140256615A1

  公开（公告）日：2014-09-11
• PEPTIDE-BASED QUORUM SENSING INHIBITORS FOR THE ATTENUATION OF VIRULENCE IN STAPHYLOCOCCUS AUREUS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20160194360A1

  公开（公告）日：2016-07-07

  Compounds that affect quorum sensing (QS) in Staphylococcus aureus and related Staphylococcus species (e.g., S. epidermidis ). Compounds which modulate one or more of the four AgrC receptors of Staphylococcus species, particularly of Staphylococcus aureus . Modulation includes inhibition or activation of one or more of these four AgrC receptors. These compounds are useful for bacterial interference and are useful for treating bacterial infections, particularly staphylococcal infection. Treatment can include combination of one or more of the compounds of the invention in combination with one or more antibiotics.
• Peptide-Based Quorum Sensing Inhibitors for the Attenuation of Virulence in Staphylococcus Aureus
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20200140489A1

  公开（公告）日：2020-05-07

  Compounds that affect quorum sensing (QS) in Staphylococcus aureus and related Staphylococcus species (e.g., S. epidermidis ). Compounds which modulate one or more of the four AgrC receptors of Staphylococcus species, particularly of Staphylococcus aureus . Modulation includes inhibition or activation of one or more of these four AgrC receptors. These compounds are useful for bacterial interference and are useful for treating bacterial infections, particularly staphylococcal infection. Treatment can include combination of one or more of the compounds of the invention in combination with one or more antibiotics.
• US9227996B2
  申请人：——

  公开号：US9227996B2

  公开（公告）日：2016-01-05