胸腺嘧啶脱氧核苷-(甲基-3H) | 52497-68-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 胸腺嘧啶脱氧核苷-(甲基-3H)
• 英文名称: (methyl-³ H)thymidine
• 英文别名: [3H]-Thymidine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(tritritiomethyl)pyrimidine-2,4-dione
• CAS: 52497-68-4
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 248.208
• InChiKey: IQFYYKKMVGJFEH-XZWYYBDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  胸腺嘧啶脱氧核苷-(甲基-3H) 生成 2-[(carbamoylamino)methyl]-3,3,3-tritritiopropanoic acid
  参考文献：
  名称：

  SHIELDS, ANTHONY F.;KOZELL, LAURA, J. LABELL. COMPOUNDS AND RADIOPHARM. , 28,(1990) N2, C. 1417-1419

  摘要：

  DOI：

文献信息

• ³H-labelled alkyl-nucleotides, -nucleosides and -bases for the immunoanalytical quantification of DNA damage and repair
  作者：Wolfgang Drosdziok、Catrin Lutze、Kai Krüger、Karl-Heinz Glüsenkamp、Manfred F. Rajewsky

  DOI：10.1002/jlcr.721

  日期：2003.8

  Analysis of the formation and repair of structurally modified DNA is of particular interest in the study of carcinogenesis, cancer therapy and aging. The quantification of specific DNA lesions by sensitive immunoanalytical methods requires radiotracers with high specific activity. We describe the synthesis of 3H-labelled adenine-, cytosine-, guanine- and thymine-alkyl derivatives by nucleophilic N- and O-alkylation using alkyl halides and diazoalkanes: 3-alkyl-[8-3H]adenine (Alkyl = Me, Et, n-Bu); O6-alkyl-deoxy[1′,2′-3H]guanosine (Alkyl = Me, Et, i-Pro, n-Bu); O6-ethyl-deoxyguanosine-5′-triphosphate ([2-3H-Ethyl]; [8-3H]); O6-alkyl-9-hydroxyhexyl-[8-3H] guanine (Alkyl=Me, Et); 7-ethyl-[8,5′-3H]guanosine-3′,5′-cyclic-phosphate; O2-andO4-alkyl-[methyl, 1′,2′-3H]thymidine (Alkyl=Me, Et); the conversion of 3H-labelled thymidine to the corresponding 5-methylcytidine; the synthesis of three different 8-oxo-guanine tracers; and the generation of thymidine glycol (5,6-dihydroxy-5,6-dihydro-[methyl-3H]thymidine) from thymidine. All radiotracers were sucessfully employed in competitive radioimmunoassays for the quantification of defined DNA alkylation products in DNA repair analyses. Copyright © 2003 John Wiley & Sons, Ltd.

  结构修饰DNA的形成与修复分析，在癌变、癌症治疗和衰老的研究中具有特殊意义。灵敏的免疫分析法测定特定DNA损伤需要高比活性的放射性示踪剂。我们描述了使用烷基卤和重氮烷通过亲核N-和O-烷基化合成3H标记的腺嘌呤、胞嘧啶、鸟嘌呤和胸腺嘧啶的烷基衍生物：3-烷基-[8-3H]腺嘌呤（烷基=甲基、乙基、正丁基）；O6-烷基-脱氧[1′,2′-3H]鸟苷（烷基=甲基、乙基、异丙基、正丁基）；O6-乙基-脱氧鸟苷-5′-三磷酸（[2-3H-乙基]；[8-3H]）；O6-烷基-9-羟基己基-[8-3H]鸟嘌呤（烷基=甲基、乙基）；7-乙基-[8,5′-3H]鸟苷-3′,5′-环磷酸酯；O2和O4-烷基-[甲基, 1′,2′-3H]胸苷（烷基=甲基、乙基）；将3H标记的胸苷转化为相应的5-甲基胞苷；三种不同8-氧代鸟嘌呤示踪剂的合成；以及从胸苷生成胸苷乙二醇（5,6-二羟基-5,6-二氢-[甲基-3H]胸苷）。所有放射性示踪剂均成功用于竞争性放射免疫分析，以量化DNA修复分析中的特定DNA烷基化产物。版权所有 © 2003 John Wiley & Sons, Ltd.
• Bis(pivaloyloxymethyl) thymidine 5′-phosphate is a cell membrane-permeable precursor of thymidine 5′-phosphate in thymidine kinase deficient CCRF CEM cells
  作者：Saeed R. Khan、Billie Nowak、William Plunkett、David Farquhar

  DOI：10.1016/j.bcp.2005.02.008

  日期：2005.5

  Bis(pivaloyloxymethyl) thymidine 5-phosphate (POM2-dTMP) has been investigated as a membrane-permeable prodrugs of dTMP. The growth inhibitory activity of POM2-TMP has been compared with thymidine (TdR) in wild type CCRF CEM cells (CEM) and a strain that lacks TdR kinase (CEM tk-). After 72 h incubation at 37 degrees C, TdR showed significant antiproliferative activity (IC50 = 27 mu M) against CEM cells but was weakly effective (IC50 = 730 mu M) against the mutant cell line. By comparison, bis(pivaloyloxymethyl) thymidine 5'-monophosphate (POM2-dTMP) was equally inhibitory (IC50 = 5 mu M) to both cell lines. The growth inhibitory effects were reversed by deoxycytidine. Cellular [methyl-H-3]dTTP pools increased linearly over 2 h during incubation of CEM or CEM tk- with 5 mu M POM2-[methyl-H-3]dTMP. The incorporation of [methyl-H-3]TdR into HClO4-insoluble cell residue by CEM tk-was < 0.1% that of CEM and did not increase over I h. In contrast, CEM tk- incorporated radioactivity from POM2-dTMP into acid insoluble residue at a rate 59% that of CEM. These results demonstrate that POM2-dTMP can penetrate into cells and serve as a source of dTMP. (c) 2005 Elsevier Inc. All rights reserved.
• SHIELDS, ANTHONY F.;KOZELL, LAURA, J. LABELL. COMPOUNDS AND RADIOPHARM. , 28,(1990) N2, C. 1417-1419
  作者：SHIELDS, ANTHONY F.、KOZELL, LAURA

  DOI：——

  日期：——
• AGGARWAL, SUNIL K.;SHALINSKY, DAVID R.;AGRAWAL, KRISHNA C., J. LABELL. COMPOUNDS AND RADIOPHARM., 25,(1988) N 10, C. 1055-1060
  作者：AGGARWAL, SUNIL K.、SHALINSKY, DAVID R.、AGRAWAL, KRISHNA C.

  DOI：——

  日期：——