2-amino-6-(3-[131I]iodobenzyloxy)-9H-purine | 321195-50-0

• 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: 2-amino-6-(3-[131I]iodobenzyloxy)-9H-purine
• 英文别名: 6-(3-[(131)I]iodo-benzyloxy)-9H-purin-2-ylamine；O(6)-(3-Iodobenzyl)guanine I-131；6-[(3-(131I)iodanylphenyl)methoxy]-7H-purin-2-amine
• CAS: 321195-50-0
• 化学式: C₁₂H₁₀IN₅O
• 分子量: 371.244
• InChiKey: IRRAGWYGQHFFCC-IQTOPCCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  C₁₈H₂₄⁽¹³¹⁾IN₅O₂Si 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 2-amino-6-(3-[131I]iodobenzyloxy)-9H-purine
  参考文献：
  名称：

  [EN] COMPOSITIONS, METHODS, AND KITS FOR DETERMINING AN ALKYL TRANSFERASE
  [FR] COMPOSITIONS, PROCÉDÉS ET TROUSSES POUR DÉTERMINER UNE ALKYL TRANSFÉRASE

  摘要：

  公开号：

  WO2011028507A3

文献信息

• [EN] COMPOSITIONS, METHODS, AND KITS FOR DETERMINING AN ALKYL TRANSFERASE<br/>[FR] COMPOSITIONS, PROCÉDÉS ET TROUSSES POUR DÉTERMINER UNE ALKYL TRANSFÉRASE
  申请人：UNIV DUKE

  公开号：WO2011028507A3

  公开（公告）日：2011-07-14
• Synthesis of ¹³¹I-Labeled Glucose-Conjugated Inhibitors of <i>O</i>⁶-Methylguanine-DNA Methyltransferase (MGMT) and Comparison with Nonconjugated Inhibitors as Potential Tools for in Vivo MGMT Imaging
  作者：Ute Mühlhausen、Ralf Schirrmacher、Markus Piel、Bernd Lecher、Manuela Briegert、Andrea Piee-Staffa、Bernd Kaina、Frank Rösch

  DOI：10.1021/jm050588q

  日期：2006.1.1

  O-6-Substituted guanine derivatives are powerful agents used for tumor cell sensitization by inhibition of the DNA repair enzyme O-6-methylguanine-DNA methyltransferase (MGMT). To provide targeted accumulation of MGMT inhibitors in tumor tissue as well as tools for in vivo imaging, we synthesized iodinated C-8-alkyl-linked glucose conjugates of 2-amino-6-(5-iodothenyl)-9H-purine (O-6-(5-iodothenyl) guanine, ITG) and 2-amino-6-(3-iodobenzyloxy)-9H-purine (O-6-(5-iodobenzyl) guanine, IBG). These compounds have MGMT inhibitor constants (IC50 values) of 0.8 and 0.45 mu M for ITGG and IBGG, respectively, as determined in HeLa S3 cells after 2-h incubation with inhibitor. To substantiate that the I-131-(hetero)arylmethylene group at the O-6-position of guanine is transferred to MGMT, both the glucose conjugated inhibitors ITGG and IBGG and the corresponding nonglucose conjugated compounds ITG and IBG were labeled with iodine-131. The radioiodinations of all compounds with [I-131]I- were performed with radiochemical yields of > 70% for the destannylation of the corresponding tri-n-butylstannylated precursors. The binding ability of [I-131]ITGG, [(131)]IBGG, [I-131]ITG, and [I-131]IBG to purified MGMT was tested. All radioactive compounds were substrates for MGMT, as demonstrated using a competitive repair assay. The newly synthesized radioactive inhibitors were utilized to study ex vivo biodistribution in mice, and the tumor-to-blood ratio of tissue uptake of [I-131]IBG and [I-131]IBGG was determined to be 0.24 and 0.76 after 0.5 h, respectively.