3-[[(3S,3aS,6R,6aS)-6-(3-aminopropoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]propan-1-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 3-[[(3S,3aS,6R,6aS)-6-(3-aminopropoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]propan-1-amine
• 化学式: C₁₂H₂₄N₂O₄
• 分子量: 260.334
• InChiKey: XFDLDISETPZLMX-USZNOCQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-环氧十二烷 、 3-[[(3S,3aS,6R,6aS)-6-(3-aminopropoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]propan-1-amine 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 生成 Lipid DIM1
  参考文献：
  名称：

  LNP-RNA-engineered adipose stem cells for accelerated diabetic wound healing

  摘要：

  Adipose stem cells (ASCs) have attracted considerable attention as potential therapeutic agents due to their ability to promote tissue regeneration. However, their limited tissue repair capability has posed a challenge in achieving optimal therapeutic outcomes. Herein, we conceive a series of lipid nanoparticles to reprogram ASCs with durable protein secretion capacity for enhanced tissue engineering and regeneration. In vitro studies identify that the isomannide-derived lipid nanoparticles (DIM1T LNP) efficiently deliver RNAs to ASCs. Co-delivery of self-amplifying RNA (saRNA) and E3 mRNA complex (the combination of saRNA and E3 mRNA is named SEC) using DIM1T LNP modulates host immune responses against saRNAs and facilitates the durable production of proteins of interest in ASCs. The DIM1T LNP-SEC engineered ASCs (DS-ASCs) prolong expression of hepatocyte growth factor (HGF) and C-X-C motif chemokine ligand 12 (CXCL12), which show superior wound healing efficacy over their wild-type and DIM1T LNP-mRNA counterparts in the diabetic cutaneous wound model. Overall, this work suggests LNPs as an effective platform to engineer ASCs with enhanced protein generation ability, expediting the development of ASCs-based cell therapies.

  DOI：

  10.1038/s41467-024-45094-5
• 作为产物：
  描述：

  L-山梨糖醇 在 dimethyl sulfide borane 、 sodium ethanolate 、 碳酸二甲酯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 3-[[(3S,3aS,6R,6aS)-6-(3-aminopropoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]propan-1-amine
  参考文献：
  名称：

  LNP-RNA-engineered adipose stem cells for accelerated diabetic wound healing

  摘要：

  Adipose stem cells (ASCs) have attracted considerable attention as potential therapeutic agents due to their ability to promote tissue regeneration. However, their limited tissue repair capability has posed a challenge in achieving optimal therapeutic outcomes. Herein, we conceive a series of lipid nanoparticles to reprogram ASCs with durable protein secretion capacity for enhanced tissue engineering and regeneration. In vitro studies identify that the isomannide-derived lipid nanoparticles (DIM1T LNP) efficiently deliver RNAs to ASCs. Co-delivery of self-amplifying RNA (saRNA) and E3 mRNA complex (the combination of saRNA and E3 mRNA is named SEC) using DIM1T LNP modulates host immune responses against saRNAs and facilitates the durable production of proteins of interest in ASCs. The DIM1T LNP-SEC engineered ASCs (DS-ASCs) prolong expression of hepatocyte growth factor (HGF) and C-X-C motif chemokine ligand 12 (CXCL12), which show superior wound healing efficacy over their wild-type and DIM1T LNP-mRNA counterparts in the diabetic cutaneous wound model. Overall, this work suggests LNPs as an effective platform to engineer ASCs with enhanced protein generation ability, expediting the development of ASCs-based cell therapies.

  DOI：

  10.1038/s41467-024-45094-5