KY-62

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: KY-62
• 英文别名: KY52；(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-N-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl]-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxamide
• 化学式: C₆₀H₁₀₀N₂O₂₂
• 分子量: 1201.45
• InChiKey: KQQVTRAMQSUSCU-NRJAXUQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  84
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  367
• 氢给体数：
  12
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  六甘醇 在 二苯基膦叠氮化物 、 sodium hydride 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 148.5h， 生成 KY-62
  参考文献：
  名称：

  Micelle/Monomer Control over the Membrane-Disrupting Properties of an Amphiphilic Antibiotic

  摘要：

  A homologous series of amphotericin B-oligo(ethylene glycol) conjugates has been synthesized, via condensation of the carboxylic acid group of amphotericin Ii with oligo(ethylene glycol)-substituted amines [NH2(CH2CH2O)(n)CH3, where n = 1, 6, 15], and examined with respect to their aggregation properties and their ability to disrupt the membrane integrity of Candida albicans and human red Mood cells. Incremental in the size of the oligo(ethylene glycol) moiety leads to a significant increase in the critical micelle concentration of the macrolide and to a corresponding increase in the concentration that is required for hemolysis In sharp contrast, the same increase in oligo(ethylene glycol) size affords only a modest reduction in antifungal activity; the net result is a separation of antifungal and hemolytic activity. These results clearly highlight the need for taking into account the aggregation properties of membrane-disrupting antibiotics with respect to target recognition and specificity and also with regard to rational molecular design.

  DOI：

  10.1021/ja00128a011

文献信息

• Micelle/Monomer Control over the Membrane-Disrupting Properties of an Amphiphilic Antibiotic
  作者：Keiji Yamashita、Vaclav Janout、Edward Bernard、Donald Armstrong、Steven L. Regen

  DOI：10.1021/ja00128a011

  日期：1995.6

  A homologous series of amphotericin B-oligo(ethylene glycol) conjugates has been synthesized, via condensation of the carboxylic acid group of amphotericin Ii with oligo(ethylene glycol)-substituted amines [NH2(CH2CH2O)(n)CH3, where n = 1, 6, 15], and examined with respect to their aggregation properties and their ability to disrupt the membrane integrity of Candida albicans and human red Mood cells. Incremental in the size of the oligo(ethylene glycol) moiety leads to a significant increase in the critical micelle concentration of the macrolide and to a corresponding increase in the concentration that is required for hemolysis In sharp contrast, the same increase in oligo(ethylene glycol) size affords only a modest reduction in antifungal activity; the net result is a separation of antifungal and hemolytic activity. These results clearly highlight the need for taking into account the aggregation properties of membrane-disrupting antibiotics with respect to target recognition and specificity and also with regard to rational molecular design.