N-isobutyroyl-5’-L-Lys(OMe)-2’,3’-di-O-(palmitoyl)guanosine monohydrochloride | 1453185-75-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-isobutyroyl-5’-L-Lys(OMe)-2’,3’-di-O-(palmitoyl)guanosine monohydrochloride
• 英文别名: [(2S,3S,4R,5R)-2-[[(2S)-6-amino-1-methoxy-1-oxohexan-2-yl]carbamoyl]-4-hexadecanoyloxy-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] hexadecanoate;hydrochloride
• CAS: 1453185-75-5
• 化学式: C₅₃H₉₁N₇O₁₀*ClH
• 分子量: 1022.81
• InChiKey: MRTOWUWQUDRWKF-LRYXIMQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.61
• 重原子数：
  71
• 可旋转键数：
  43
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  232
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  N-isobutyroyl-5’-carboxy-2’,3’-di-O-(carbobenzyloxy)guanosine 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.67h， 生成 N-isobutyroyl-5’-L-Lys(OMe)-2’,3’-di-O-(palmitoyl)guanosine monohydrochloride
  参考文献：
  名称：

  Synthesis, DNA binding and anti-leukemic activity of an aminoacyl nucleolipid

  摘要：

  The synthesis and characterization of a new class of DNA binding molecule exhibiting potent and selective anti-leukemic activity is described. The synthesis of an aminoacyl nucleolipid was developed from an efficient EEDQ coupling strategy, in which a series of seven bioconjugates were synthesized in yields of 53-78%. Guanosine bioconjugate 7, was used as building block for the synthesis of a target aminoacyl nucleolipid 14. Its GRP78 DNA binding affinity was confirmed by gel shift assay, CD spectroscopy, T-m measurements and dynamic light scattering experiments. Moreover, in a single dose (10 mu M) screen against a panel of 60 cancer cell lines, aminoacyl nucleolipid 14 was found to selectively trigger greater than 90% cell death in a SR human leukemia cancer cell line. The reported aminoacyl nucleolipid represents a useful model for a new class of DNA binding molecules for the development of potent and selective anti-cancer agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.07.030

文献信息

• Synthesis, DNA binding and anti-leukemic activity of an aminoacyl nucleolipid
  作者：Pradeepkumar Patel、Emi Hanawa、Reeta Yadav、Uri Samuni、Cecilia Marzabadi、David Sabatino

  DOI：10.1016/j.bmcl.2013.07.030

  日期：2013.9

  The synthesis and characterization of a new class of DNA binding molecule exhibiting potent and selective anti-leukemic activity is described. The synthesis of an aminoacyl nucleolipid was developed from an efficient EEDQ coupling strategy, in which a series of seven bioconjugates were synthesized in yields of 53-78%. Guanosine bioconjugate 7, was used as building block for the synthesis of a target aminoacyl nucleolipid 14. Its GRP78 DNA binding affinity was confirmed by gel shift assay, CD spectroscopy, T-m measurements and dynamic light scattering experiments. Moreover, in a single dose (10 mu M) screen against a panel of 60 cancer cell lines, aminoacyl nucleolipid 14 was found to selectively trigger greater than 90% cell death in a SR human leukemia cancer cell line. The reported aminoacyl nucleolipid represents a useful model for a new class of DNA binding molecules for the development of potent and selective anti-cancer agents. Published by Elsevier Ltd.