6,25-diaza-10,13,16,19,22-pentaoxa-7,26-dioxo-35,37-pentakontadiynyl-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosylonic acid | 1261156-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,25-diaza-10,13,16,19,22-pentaoxa-7,26-dioxo-35,37-pentakontadiynyl-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosylonic acid
• 英文别名: 6,25-diaza-10,13,16,19,22-pentaoxa-7,26-dioxo-35,37-pentakontadiynyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosylonic acid；alpha-Neuraminic acid, N-acetyl-2-O-(7,26-dioxo-10,13,16,19,22-pentaoxa-6,25-diazapentaconta-35,37-diyn-1-yl)-；(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[5-[3-[2-[2-[2-[2-[2-(pentacosa-10,12-diynoylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]pentoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1261156-82-4
• 化学式: C₅₄H₉₅N₃O₁₆
• 分子量: 1042.36
• InChiKey: VRJMVFQLUBTBKF-HBJHFNNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  73
• 可旋转键数：
  49
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  270
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4-acetoxy-6-((5-aminopentyl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 哌啶 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 生成 6,25-diaza-10,13,16,19,22-pentaoxa-7,26-dioxo-35,37-pentakontadiynyl-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosylonic acid
  参考文献：
  名称：

  Molecular Wipes: Application to Epidemic Keratoconjuctivitis

  摘要：

  Epidemic keratoconjunctivitis (EKC) is a severe disease of the eye, caused by members of the Adenoviridae (Ad) family, with symptoms such as keratitis, conjunctivitis, pain, edema, and reduced vision that may last for months or years. There are no vaccines or antiviral drugs available to prevent or treat EKC. It was found previously that EKC-causing Ads use sialic acid as a cellular receptor and demonstrated that soluble, sialic acid-containing molecules can prevent infection. In this study, multivalent sialic acid constructs based on 10,12-pentacosadiynoic acid (PDA) have been synthesized, and these constructs are shown to be efficient inhibitors of Ad binding (IC50 = 0.9 mu M) and Ad infectivity (IC50 = 0.7 mu M). The mechanism of action is to aggregate virus particles and thereby prevent them from binding to ocular cells. Such formulations may be used for topical treatment of adenovirus-caused EKC.

  DOI：

  10.1021/jm200545m

文献信息

• Molecular Wipes: Application to Epidemic Keratoconjuctivitis
  作者：Karolina Aplander、Marko Marttila、Sophie Manner、Niklas Arnberg、Olov Sterner、Ulf Ellervik

  DOI：10.1021/jm200545m

  日期：2011.10.13

  Epidemic keratoconjunctivitis (EKC) is a severe disease of the eye, caused by members of the Adenoviridae (Ad) family, with symptoms such as keratitis, conjunctivitis, pain, edema, and reduced vision that may last for months or years. There are no vaccines or antiviral drugs available to prevent or treat EKC. It was found previously that EKC-causing Ads use sialic acid as a cellular receptor and demonstrated that soluble, sialic acid-containing molecules can prevent infection. In this study, multivalent sialic acid constructs based on 10,12-pentacosadiynoic acid (PDA) have been synthesized, and these constructs are shown to be efficient inhibitors of Ad binding (IC50 = 0.9 mu M) and Ad infectivity (IC50 = 0.7 mu M). The mechanism of action is to aggregate virus particles and thereby prevent them from binding to ocular cells. Such formulations may be used for topical treatment of adenovirus-caused EKC.