5-acetamido-2,4,7,8,9-penta-O-butanoyl-3,5-dideoxy-1-methyl ester-D-glycero-D-galacto-2-nonulopyranosonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-2,4,7,8,9-penta-O-butanoyl-3,5-dideoxy-1-methyl ester-D-glycero-D-galacto-2-nonulopyranosonic acid
• 英文别名: Bu5Neu5AcOMe；methyl 5-actamido-2,4,7,8,9-penta-O-butanoyl-2,5-dideoxy-α,β-D-glycero-D-galactononulosonate；methyl (4S,5R,6R)-5-acetamido-2,4-di(butanoyloxy)-6-[(1S,2R)-1,2,3-tri(butanoyloxy)propyl]oxane-2-carboxylate
• 化学式: C₃₂H₅₁NO₁₄
• 分子量: 673.755
• InChiKey: JHURDXMYOJRAOV-IRJVQHLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  47
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 4-二甲氨基吡啶 吡啶 作用下， 反应 48.0h， 生成 5-acetamido-2,4,7,8,9-penta-O-butanoyl-3,5-dideoxy-1-methyl ester-D-glycero-D-galacto-2-nonulopyranosonic acid
  参考文献：
  名称：

  [EN] HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS
  [FR] MONOSACCHARIDES HYBRIDES DÉRIVATISÉS AVEC HYDROXYLE /SCFA (ACIDES GRAS À CHAÎNE COURTE), PROCÉDÉS DE SYNTHÈSE, ET PROCÉDÉS DE TRAITEMENT DE TROUBLES

  摘要：

  本文描述了脂肪酸碳水化合物及其衍生物，以及利用这些化合物及其组合物治疗或预防疾病和疾病症状的方法。

  公开号：

  WO2009020641A1

文献信息

• Targeting Pro-Invasive Oncogenes with Short Chain Fatty Acid-Hexosamine Analogues Inhibits the Mobility of Metastatic MDA-MB-231 Breast Cancer Cells
  作者：Christopher T. Campbell、Udayanath Aich、Christopher A. Weier、Jean J. Wang、Sean S. Choi、Mary M. Wen、Katharina Maisel、Srinivasa-Gopalan Sampathkumar、Kevin J. Yarema

  DOI：10.1021/jm800873k

  日期：2008.12.25

  Per-butanoylated N-acetyl-D-mannosamine (Bu(4)ManNAc), a SCFA-hexosamine cancer drug candidate with activity manifest through intact n-butyrate-carbohydrate linkages, reduced the invasion of metastatic MDA-MB-231 breast cancer cells unlike per-butanoylated-D-mannose (Bu(5)Man), a clinically tested compound that did not alter cell mobility. To gain molecular-level insight, therapeutic targets implicated in metastasis were investigated. The active compound Bu(4)ManNAc reduced both MUC1 expression and MMP-9 activity (via down-regulation of CXCR4 transcription), whereas "inactive" Bu(5)Man had counterbalancing effects on these oncogenes. This divergent impact on transcription was linked to interplay between HDACi activity (held by both Bu(4)ManNAc and Bu(5)Man) and NF-kappa B activity, which was selectively down-regulated by Bu(4)ManNAc. Overall, these results establish a new therapeutic end point (control of invasion) for SCFA-hexosamine hybrid molecules, define relative contributions of molecular players involved in cell mobility and demonstrate that Bu(4)ManNAc breaks the confounding link between beneficial HDACi activity and the simultaneous deleterious activation of NF-kappa B often found in epigenetic drug candidates.
• [EN] HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS<br/>[FR] MONOSACCHARIDES HYBRIDES DÉRIVATISÉS AVEC HYDROXYLE /SCFA (ACIDES GRAS À CHAÎNE COURTE), PROCÉDÉS DE SYNTHÈSE, ET PROCÉDÉS DE TRAITEMENT DE TROUBLES
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2009020641A1

  公开（公告）日：2009-02-12

  Described herein are fatty acid carbohydrate-hydroxyl-hybrid compounds and derivatives thereof, and methods of treating or preventing disease and disease symptoms using the compounds and compositions thereof.

  本文描述了脂肪酸碳水化合物及其衍生物，以及利用这些化合物及其组合物治疗或预防疾病和疾病症状的方法。