9-[beta-D-Fructopyranosyl]-adenine | 54933-77-6

• 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: 9-[beta-D-Fructopyranosyl]-adenine
• 英文别名: 9-β-D-fructopyranosyladenine；5-(6-amino-purin-9-yl)-1,5-anhydro-D-mannitol；5-(6-Amino-purin-9-yl)-1,5-anhydro-D-mannit；(2R,3S,4R,5R)-2-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 54933-77-6
• 化学式: C₁₁H₁₅N₅O₅
• 分子量: 297.271
• InChiKey: ZBQAOPITTZCBNI-ICQCTTRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-[beta-D-Fructopyranosyl]-adenine 在 E_. coli purine nucleoside phosphorylase 作用下， 生成 腺嘌呤 、
  参考文献：
  名称：

  Gene Therapy of Cancer: Activation of Nucleoside Prodrugs withE. coliPurine Nucleoside Phosphorylase

  摘要：

  During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery off. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data.

  DOI：

  10.1080/15257779908041562
• 作为产物：
  描述：

  1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide 、 alkaline earth salt of/the/ methylsulfuric acid 在 xylene 作用下， 生成 9-[beta-D-Fructopyranosyl]-adenine
  参考文献：
  名称：

  Potential Anticancer Agents.¹ XXVI. Synthesis of Nucleosides Derived from D-Fructose

  摘要：

  DOI：

  10.1021/jo01093a005

文献信息

• Mutant purine nucleoside phosphorylase proteins and cellular delivery thereof
  申请人：Ealick E. Steven

  公开号：US20050214901A1

  公开（公告）日：2005-09-29

  A host cell stably transformed or transfected by a vector including a DNA sequence encoding for mutant purine nucleoside cleavage enzymes is provided. The transformed or transfected host cell can be used in combination with a purine substrate to treat tumour cells and/or virally infected cells. A nucleotide sequence encoding mutant E. coli derived purine nucleoside phosphorylase proteins which can be used in conjunction with an appropriate substrate to produce toxins which impair abnormal cell growth is also provided. A method is detailed for the delivery of toxin by generation withing target cells or by administration and delivery to the cells from without. Novel purine nucleosides are detailed that yield a cytotoxic purine upn enzymatic cleavage. A synthetic process for nucleosides is also detailed.

  提供了一种由载有突变嘌呤核苷酸裂解酶编码DNA序列的载体转化或转染的宿主细胞。该转化或转染的宿主细胞可与嘌呤底物结合，用于治疗肿瘤细胞和/或病毒感染的细胞。还提供了编码突变E. coli来源的嘌呤核苷酰化酶蛋白的核苷酸序列，可与适当的底物结合使用，产生有害细胞生长的毒素。详细介绍了一种通过靶细胞内生成或通过外部给药和传递给细胞的毒素递送方法。详细介绍了产生细胞毒性嘌呤核苷酶裂解产物的新型嘌呤核苷。还详细介绍了一种核苷的合成过程。
• US7037718B2
  申请人：——

  公开号：US7037718B2

  公开（公告）日：2006-05-02
• US7488598B2
  申请人：——

  公开号：US7488598B2

  公开（公告）日：2009-02-10
• Gene Therapy of Cancer: Activation of Nucleoside Prodrugs with<i>E. coli</i>Purine Nucleoside Phosphorylase
  作者：John A. Secrist、William B. Parker、Paula W. Allan、L. Lee Bennett、William R. Waud、Jackie W. Truss、Anita T. Fowler、John A. Montgomery、Steven E. Ealick、Alan H. Wells、G. Yancey Gillespie、V. K. Gadi、Eric J. Sorscher

  DOI：10.1080/15257779908041562

  日期：1999.4

  During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery off. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data.
• Potential Anticancer Agents.¹ XXVI. Synthesis of Nucleosides Derived from D-Fructose
  作者：ELMER J. REIST、PHILLIP A. HART、B. R. BAKER

  DOI：10.1021/jo01093a005

  日期：1959.11