1,36-bis(2,3-dihydroxybenzoyl)-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]hexatriacontane | 1154500-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,36-bis(2,3-dihydroxybenzoyl)-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]hexatriacontane
• 英文别名: (4S,5R)-N-[3-[3-[(2,3-dihydroxybenzoyl)amino]propyl-[(4S,5R)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]propyl]-N-[4-[3-[[3-[4-[3-[3-[(2,3-dihydroxybenzoyl)amino]propyl-[(4S,5R)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]propyl-[(4S,5R)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]butylamino]-3-oxopropyl]disulfanyl]propanoylamino]butyl]-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxamide
• CAS: 1154500-50-1
• 化学式: C₈₄H₁₀₂N₁₂O₂₄S₂
• 分子量: 1727.93
• InChiKey: JTNZPLYPALSTLP-ODRRTXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  122
• 可旋转键数：
  43
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  577
• 氢给体数：
  16
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  1,36-bis(2,3-dihydroxybenzoyl)-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]hexatriacontane 在 氢气 、 钯 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到1-(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane
  参考文献：
  名称：

  Vibriobactin Antibodies: A Vaccine Strategy

  摘要：

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.

  DOI：

  10.1021/jm900119q
• 作为产物：
  描述：

  1,36-bis(2,3-dihydroxybenzoyl)-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis(L-threonyl)hexatriacontane tetrakis(trifluoroacetate) 、 ethyl 2,3-dihydroxybenzimidate 以 乙醇 为溶剂， 反应 36.0h， 以20%的产率得到1,36-bis(2,3-dihydroxybenzoyl)-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]hexatriacontane
  参考文献：
  名称：

  Vibriobactin Antibodies: A Vaccine Strategy

  摘要：

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.

  DOI：

  10.1021/jm900119q

文献信息

• Siderophore Conjugate Immunogenic Compositions and Vaccines
  申请人：Bergeron, JR. Raymond J.

  公开号：US20120052087A1

  公开（公告）日：2012-03-01

  An immunogenic composition comprising a siderophore covalently linked to a pharmaceutically acceptable carrier molecule wherein the antigenicity of the siderophore moiety is sufficient to stimulate an immuno-logic response to the siderophore when the composition is circulating in the bloodstream of a human or non-human animal and vaccine.

  一种免疫原性组合物，包括一个与药用可接受载体分子共价连接的铁载体，其中铁载体部分的抗原性足以在该组合物在人类或非人类动物的血液循环中循环时刺激对铁载体的免疫反应，从而形成疫苗。
• Vibriobactin Antibodies: A Vaccine Strategy
  作者：Raymond J. Bergeron、Neelam Bharti、Shailendra Singh、James S. McManis、Jan Wiegand、Linda G. Green

  DOI：10.1021/jm900119q

  日期：2009.6.25

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.