5-(6-amino-8-(4-(trifluoromethyl)styryl)-9H-purin-9-yl)-2-((bis(4-methoxy-phenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol | 1609552-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(6-amino-8-(4-(trifluoromethyl)styryl)-9H-purin-9-yl)-2-((bis(4-methoxy-phenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol
• CAS: 1609552-34-2
• 化学式: C₄₀H₃₆F₃N₅O₅
• 分子量: 723.752
• InChiKey: HOBJAQXFPHRHGP-MLLGDHKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  53.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  126.77
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-(6-amino-8-(4-(trifluoromethyl)styryl)-9H-purin-9-yl)-2-((bis(4-methoxy-phenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol 、 N,N-二甲基甲酰胺二甲基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以99%的产率得到N'-(9-(5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-8-(4-(trifluoromethyl)styryl)-9H-purin-6-yl)-N,N-dimethylformimidamide
  参考文献：
  名称：

  Development of fluorescent double-strand probes labeled with 8-(p-CF3-cinnamyl)-adenosine for the detection of cyclin D1 breast cancer marker

  摘要：

  Fluorescent nucleoside analogs replacing natural DNA bases in an oligonucleotide have been widely used for the detection of genetic material. Previously, we have described 2-((4-(trifluoromethyl) phenyl)trans-vinyl)-2 '-deoxy-adenosine, 6, a nucleoside analog with intrinsic fluorescence (NIF). Analog 6 exhibits a quantum yield 3115-fold higher than that of adenosine (phi 0.81) and maximum emission which is 120 nm red shifted (lambda(em) 439 nm). Here, we incorporated this analog in one or several positions of cyclin Dl-targeting 15-mer oligonucleotides (ONs). The fluorescence of 6 was quenched upon incorporation into an oligonucleotide (ca. 1.5-22 fold), and was further reduced upon duplex formation. Specifically, 0N7 exhibited a fluorescence decrease of ca. 2- or 3-fold upon duplex formation with complementary DNA or RNA strand, respectively. We determined the kinetics of dehybridization/rehybridization process in the presence of ssDNA or ssRNA targets to optimize our probes length and established the probes' selectivity towards a specific target. Furthermore, we proved specificity of our probe to the target vs. singly mismatched targets. Our most promising ds-NIF-probe, ON7:RNA, was used for the detection of cyclin D1 mRNA marker in cancerous cells total RNA extracts. The ds-probe specifically recognized the target as observed by a 2-fold fluorescence increase within 30 s at RT. These findings illustrate the potential of ds-NIF-probes for the diagnosis of breast cancer. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.081
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 4-二甲氨基吡啶 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 、 三乙胺 作用下， 以 吡啶 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 5-(6-amino-8-(4-(trifluoromethyl)styryl)-9H-purin-9-yl)-2-((bis(4-methoxy-phenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Development of fluorescent double-strand probes labeled with 8-(p-CF3-cinnamyl)-adenosine for the detection of cyclin D1 breast cancer marker

  摘要：

  Fluorescent nucleoside analogs replacing natural DNA bases in an oligonucleotide have been widely used for the detection of genetic material. Previously, we have described 2-((4-(trifluoromethyl) phenyl)trans-vinyl)-2 '-deoxy-adenosine, 6, a nucleoside analog with intrinsic fluorescence (NIF). Analog 6 exhibits a quantum yield 3115-fold higher than that of adenosine (phi 0.81) and maximum emission which is 120 nm red shifted (lambda(em) 439 nm). Here, we incorporated this analog in one or several positions of cyclin Dl-targeting 15-mer oligonucleotides (ONs). The fluorescence of 6 was quenched upon incorporation into an oligonucleotide (ca. 1.5-22 fold), and was further reduced upon duplex formation. Specifically, 0N7 exhibited a fluorescence decrease of ca. 2- or 3-fold upon duplex formation with complementary DNA or RNA strand, respectively. We determined the kinetics of dehybridization/rehybridization process in the presence of ssDNA or ssRNA targets to optimize our probes length and established the probes' selectivity towards a specific target. Furthermore, we proved specificity of our probe to the target vs. singly mismatched targets. Our most promising ds-NIF-probe, ON7:RNA, was used for the detection of cyclin D1 mRNA marker in cancerous cells total RNA extracts. The ds-probe specifically recognized the target as observed by a 2-fold fluorescence increase within 30 s at RT. These findings illustrate the potential of ds-NIF-probes for the diagnosis of breast cancer. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.081