6-amino-9-(10-amino-3,7-diazadecyl)-9H-purine | 114882-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-amino-9-(10-amino-3,7-diazadecyl)-9H-purine
• 英文别名: N'-[3-[2-(6-aminopurin-9-yl)ethylamino]propyl]propane-1,3-diamine
• CAS: 114882-25-6
• 化学式: C₁₃H₂₄N₈
• 分子量: 292.387
• InChiKey: SWYRVXSVFDGSFV-UHFFFAOYSA-N

物化性质

• 沸点：
  544.6±60.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-amino-9-(10-amino-3,7-diazadecyl)-9H-purine 在 sodium hydroxide 、 pH=4 buffer 、 四丁基氟化铵 、 溴 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 N¹-[3-(4-Amino-7,8-dihydro-imidazo[1,2-e]purin-6-yl)-propyl]-propane-1,3-diamine
  参考文献：
  名称：

  Synthesis of an imidazo[1,2-e]purine-acridine heterodimer for targeting abasic sites in DNA

  摘要：

  Cyclization of 8-bromo-9-alkylaminoethyl-adenine quantitatively affords a substituted imidazo[1,2-e]purine. The corresponding heterodimer, imidazo[1,2-e]purine-acridine, was prepared and its interaction with abasic site containing oligonucleotides was studied. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00703-3
• 作为产物：
  描述：

  腺嘌呤 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 6-amino-9-(10-amino-3,7-diazadecyl)-9H-purine
  参考文献：
  名称：

  A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency

  摘要：

  A series of tailor-made molecules, 1 and 4-7, have been prepared to recognize and cleave DNA at apurinic sites. These molecules incorporate in their structure different units designed for specific functions: (1) an intercalator for DNA binding, (2) a nucleic base for abasic site recognition, and (3) a linker endowed with both a binding function and a cleavage function (Scheme II). The constituent units were varied successively in the series of molecules to get insight into their mode of action and prepare more active compounds. H-1 NMR spectroscopy reveals the absence of intramolecular ring-ring stacking interactions in water between the base and the intercalator in all molecules 1 and 4-7. All bind to calf thymus DNA with binding constants ranging from 10(4) to 10(6) M-1. Their nuclease activity was estimated by measuring their ability to induce single strand breaks in depurinated pBR 322 plasmid DNA. The most efficient molecule, 5, exhibits high recognition selectivity and cleavage efficiency: at nanomolar concentrations, 5 recognizes and cleaves the abasic lesion present in a DNA molecule containing an average of 1.8 apurinic sites in its 4 362 base pairs sequence. Molecule 5 exhibits higher cleaving efficiency than the reported tripeptide Lys-Trp-Lys: 10(-8) M concentrations of the former (5) lead to cleavage ratios comparable to those observed for the latter used as 10(-3) M concentration. This enzyme mimic 5 can be used advantageously as a substitute to the natural nuclease for in vitro cleavage of depurinated DNA.

  DOI：

  10.1021/ja00075a011

文献信息

• Design of site specific DNA damaging agents for generation of multiply damaged sites
  作者：Alain Martelli、Jean-Francois Constant、Martine Demeunynck、Jean Lhomme、Pascal Dumy

  DOI：10.1016/s0040-4020(02)00345-9

  日期：2002.5

  We describe the synthesis and DNA damaging activities of hybrid molecules in which a purine (adenine) is linked to an intercalating chromophore (acridine) by a polyamino linker. A DNA damaging agent, phenanthroline or para-nitrobenzamide, is tethered to the acridine moiety at various positions. Our goal is to induce upon activation other lesions in close proximity to the abasic site and therefore create cytotoxic multiply damaged sites. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The abasic site as a target for generation of locally multiply damaged sites
  作者：Alain Martelli、Nathalie Berthet、Jean-François Constant、Martine Demeunynck、Jean Lhomme

  DOI：10.1016/s0960-894x(00)00081-0

  日期：2000.4

  Abasic sites in DNA have been specifically targeted by synthetic compounds able to cleave DNA at abasic sites and to induce photodamages in the vicinity of the lesion. The synthesis and the photoactivity of the drugs on abasic sites containing DNA and oligonucleotides are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency
  作者：Abdellatif Fkyerat、Martine Demeunynck、Jean Francois Constant、Pierre Michon、Jean Lhomme

  DOI：10.1021/ja00075a011

  日期：1993.11

  A series of tailor-made molecules, 1 and 4-7, have been prepared to recognize and cleave DNA at apurinic sites. These molecules incorporate in their structure different units designed for specific functions: (1) an intercalator for DNA binding, (2) a nucleic base for abasic site recognition, and (3) a linker endowed with both a binding function and a cleavage function (Scheme II). The constituent units were varied successively in the series of molecules to get insight into their mode of action and prepare more active compounds. H-1 NMR spectroscopy reveals the absence of intramolecular ring-ring stacking interactions in water between the base and the intercalator in all molecules 1 and 4-7. All bind to calf thymus DNA with binding constants ranging from 10(4) to 10(6) M-1. Their nuclease activity was estimated by measuring their ability to induce single strand breaks in depurinated pBR 322 plasmid DNA. The most efficient molecule, 5, exhibits high recognition selectivity and cleavage efficiency: at nanomolar concentrations, 5 recognizes and cleaves the abasic lesion present in a DNA molecule containing an average of 1.8 apurinic sites in its 4 362 base pairs sequence. Molecule 5 exhibits higher cleaving efficiency than the reported tripeptide Lys-Trp-Lys: 10(-8) M concentrations of the former (5) lead to cleavage ratios comparable to those observed for the latter used as 10(-3) M concentration. This enzyme mimic 5 can be used advantageously as a substitute to the natural nuclease for in vitro cleavage of depurinated DNA.
• Synthesis of an imidazo[1,2-e]purine-acridine heterodimer for targeting abasic sites in DNA
  作者：Philippe Belmont、Karine Alarcon、Martine Demeunynck、Jean Lhomme

  DOI：10.1016/s0960-894x(98)00703-3

  日期：1999.1

  Cyclization of 8-bromo-9-alkylaminoethyl-adenine quantitatively affords a substituted imidazo[1,2-e]purine. The corresponding heterodimer, imidazo[1,2-e]purine-acridine, was prepared and its interaction with abasic site containing oligonucleotides was studied. (C) 1999 Elsevier Science Ltd. All rights reserved.