3-amino-N-(2-{3-[[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-(2-nitro-benzenesulfonyl)-amino]-propylcarbamoyl}-ethyl)-propionamide | 879288-20-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-amino-N-(2-{3-[[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-(2-nitro-benzenesulfonyl)-amino]-propylcarbamoyl}-ethyl)-propionamide
• CAS: 879288-20-7
• 化学式: C₄₂H₆₇N₅O₆S
• 分子量: 770.09
• InChiKey: MOCLNCRTVQQAAN-VVILRWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  54.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  164.74
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-amino-N-(2-{3-[[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-(2-nitro-benzenesulfonyl)-amino]-propylcarbamoyl}-ethyl)-propionamide 在 potassium carbonate 、 苯硫酚 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-[4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoyl]-β-alanyl-N-(3-{(3β)-cholest-5-en-3-ylamino}propyl)-β-alaninamide
  参考文献：
  名称：

  The Pennsylvania Green Fluorophore: A Hybrid of Oregon Green and Tokyo Green for the Construction of Hydrophobic and pH-Insensitive Molecular Probes

  摘要：

  Fluorescent small molecules are powerful tools for exploring cellular biology. As a more hydrophobic, photostable, and less pH-sensitive alternative to fluorescein, we synthesized Pennsylvania Green, a bright, monoanionic fluorophore related to Oregon Green and Tokyo Green. Comparison of membrane probes comprising N-alkyl-3 beta-cholesterylamine linked to 4-carboxy-Tokyo Green (pK(a) similar to 6.2) and 4-carboxy-Pennsylvania Green (pK(a) similar to 4.8) revealed that only Pennsylvania Green was highly fluorescent in acidic early and recycling endosomes within living mammalian cells.

  DOI：

  10.1021/ol052655g
• 作为产物：
  描述：

  5-胆甾烯-3-酮 在 lithium aluminium tetrahydride 、 三(2-氯乙基)胺 、 L-Selectride 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 甲苯 、 苯 为溶剂， 反应 39.0h， 生成 3-amino-N-(2-{3-[[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-(2-nitro-benzenesulfonyl)-amino]-propylcarbamoyl}-ethyl)-propionamide
  参考文献：
  名称：

  Synthetic Mimics of Small Mammalian Cell Surface Receptors

  摘要：

  Receptors on the surface of mammalian cells promote the uptake of cell-impermeable ligands by receptor-mediated endocytosis. To mimic this process, we synthesized small molecules designed to project anti-dinitrophenyl antibody-binding motifs from the surface of living Jurkat lymphocytes. These synthetic receptors comprise N-alkyl derivatives of 3beta-cholesterylamine as the plasma membrane anchor linked to 2,4-dinitrophenyl (DNP) and structurally similar fluorescent 7-nitrobenz-2-oxa-1,3-diazole (NBD) headgroups. Insertion of two beta-alanine subunits between a DNP derivative and 3beta-cholesterylamine yielded a receptor that avidly associates with cell surfaces (cellular t(1/2) similar to 20 h). When added to Jurkat cells at 10 muM, this receptor enhanced uptake of an anti-DNP IgG ligand by similar to200-fold in magnitude and similar to400-fold in rate within 4 h (ligand internalization t(1/2) similar to 95 min at 37 degreesC). This non-natural receptor mimics many natural receptors by dynamically cycling between plasma membranes and intracellular endosomes (recycling t(1/2) similar to 3 min), targeting of protein ligands to proposed cholesterol and sphingolipid-enriched lipid raft membrane microdomains, and delivery of protein ligands to late endosomes/lysosomes. Quantitative dithionite quenching of fluorescent extracellular NBD headgroups demonstrated that other 3beta-cholesterylamine derivatives bearing fewer beta-alanines in the linker region or N-acyl derivatives of 3beta-cholesterylamine were less effective receptors due to more extensive trafficking to internal membranes. Synthetic cell surface receptors have potential applications as cellular probes, tools for drug delivery, and methods to deplete therapeutically important extracellular ligands.

  DOI：

  10.1021/ja046663o