8-(methylsulfonyl)guanosine | 7057-50-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-(methylsulfonyl)guanosine
• 英文别名: 8-Methylsulfonylguanosine；2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-methylsulfonyl-1H-purin-6-one
• CAS: 7057-50-3
• 化学式: C₁₁H₁₅N₅O₇S
• 分子量: 361.335
• InChiKey: AVRXZAZVHJOTBC-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  198
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-(4-氯苯胺基)-4-氧代丁酸 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以43%的产率得到8-(methylsulfonyl)guanosine
  参考文献：
  名称：

  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells

  摘要：

  A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted-N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.

  DOI：

  10.1021/jm00147a012

文献信息

• Method for labeling and fragmenting DNA
  申请人：BIO MERIEUX

  公开号：US20030143555A1

  公开（公告）日：2003-07-31

  The invention relates to a method for labeling and fragmenting a single- or double-stranded deoxyribonucleic acid (DNA) comprising the following steps: chemically fragmenting the DNA by creating at least one abasic site on said DNA, attaching a marker to at least one of the fragments by means of a labeling reagent, said reagent covalently and predominantly coupling to at least one phosphate of said fragment. The invention finds a preferred application in the field of diagnosis.

  该发明涉及一种用于标记和分解单链或双链脱氧核糖核酸（DNA）的方法，包括以下步骤：通过在DNA上创建至少一个缺碱位点来化学分解DNA，通过标记试剂将标记物附着到至少一个片段上，该试剂以共价键和主要地耦合到至少一个片段的磷酸基。该发明在诊断领域中找到了一个首选的应用。
• PROCEDE DE MARQUAGE ET DE FRAGMENTATION D'ADN
  申请人：BIO MERIEUX

  公开号：EP1383925B1

  公开（公告）日：2006-09-20
• US7060441B2
  申请人：——

  公开号：US7060441B2

  公开（公告）日：2006-06-13
• [EN] METHOD FOR LABELLING AND FRAGMENTING DNA<br/>[FR] PROCÉDÉ DE MARQUAGE ET DE FRAGMENTATION D'ADN
  申请人：BIO MERIEUX

  公开号：WO2002090584A2

  公开（公告）日：2002-11-14

  La présente invention concerne un procédé de marquage et de fragmentation d'un acide désoxyribonucléique (ADN) simple ou double brin comprenant les étapes suivantes : fragmenter chimiquement l'ADN en créant au moins un site abasique sur ledit ADN, attacher un marqueur sur au moins un des fragments par l'intermédiaire d'un réactif de marquage, ledit réactif se couplant de manière covalente et majoritaire sur au moins un phosphate dudit fragment. L'invention trouve une application préférentielle dans le domaine du diagnostic.
• 8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells
  作者：Tai Shun Lin、Jia Chong Cheng、Kimiko Ishiguro、Alan C. Sartorelli

  DOI：10.1021/jm00147a012

  日期：1985.9

  A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted-N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.