N²-[3-methoxyestra-1,3,5(10)-trien-6β-yl]-2'-deoxyguanosine | 187404-51-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N²-[3-methoxyestra-1,3,5(10)-trien-6β-yl]-2'-deoxyguanosine
• 英文别名: 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-[[(6R,8S,9S,13S,14S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-6-yl]amino]-1H-purin-6-one
• CAS: 187404-51-9
• 化学式: C₂₉H₃₇N₅O₅
• 分子量: 535.643
• InChiKey: DPEIUKAKFNLZAU-AWMYMPSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-[3-methoxyestra-1,3,5(10)-trien-6β-yl]-2'-deoxyguanosine 在 盐酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 N²-[3-methoxyestra-1,3,5(10)-trien-6β-yl]guanine
  参考文献：
  名称：

  Identification of Estrogen-Modified Nucleosides from Calf Thymus DNA Reacted with 6-Hydroxyestrogen 6-Sulfates

  摘要：

  Two estrogen sulfates, pyridinium 3-methoxyestra-1,3,5(10)-trien-6 alpha-yl sulfate (3MeE-6 alpha-S) and its GP-isomer (3MeE-6 beta-S), synthesized as model compounds to demonstrate the carcinogenesis of estrogen, were found to react with calf thymus DNA to produce steroid-modified DNA adducts. Digestion of the DNA by nuclease P1 and phosphodiesterase I followed by alkaline phosphatase gave a deoxyribonucleoside fraction, of which N-2-[3-methoxyestra-1,3,5( 10)-trien-6 alpha-yl]deoxyguanosine, N-2-[3-methoxyestra-1,3,5( 10)-trien-6 beta-yl]deoxyguanosine, N-6-[3-methoxyestra-1,3,5(10)-trien-6 alpha-yl]deoxyadenosine, and N-6-[3-methoxyestra-1,3,5(10)trien-6 alpha-yl]deoxyadenosine (identified as a base adduct) were identified using HPLC by comparing them with authentic specimens prepared by reacting dG; and dA with both sulfates. No steroid-dC adduct was detected in the digestion products of the DNA adduct, although dC reacted with the sulfates to form N-4-[3-methoxyestra-1,3,5(10)-trien-G beta-yl] deoxycytidine, These results mean that estrogen B-sulfate has an ability to modify DNA via the amino group of a guanine or adenine residue in DNA. The present studies imply that a sequential metabolism (hydroxylation and sulfation) at the Cs-position of the estrogen molecule causes damage to DNA.

  DOI：

  10.1021/tx9800957
• 作为产物：
  描述：

  2'-脱氧鸟苷 、 pyridinium 3-methoxy-estra-1,3,5(10)-trien-6β-yl sulfate 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 0.33h， 以0.7%的产率得到N²-[3-methoxyestra-1,3,5(10)-trien-6β-yl]-2'-deoxyguanosine
  参考文献：
  名称：

  Identification of Estrogen-Modified Nucleosides from Calf Thymus DNA Reacted with 6-Hydroxyestrogen 6-Sulfates

  摘要：

  Two estrogen sulfates, pyridinium 3-methoxyestra-1,3,5(10)-trien-6 alpha-yl sulfate (3MeE-6 alpha-S) and its GP-isomer (3MeE-6 beta-S), synthesized as model compounds to demonstrate the carcinogenesis of estrogen, were found to react with calf thymus DNA to produce steroid-modified DNA adducts. Digestion of the DNA by nuclease P1 and phosphodiesterase I followed by alkaline phosphatase gave a deoxyribonucleoside fraction, of which N-2-[3-methoxyestra-1,3,5( 10)-trien-6 alpha-yl]deoxyguanosine, N-2-[3-methoxyestra-1,3,5( 10)-trien-6 beta-yl]deoxyguanosine, N-6-[3-methoxyestra-1,3,5(10)-trien-6 alpha-yl]deoxyadenosine, and N-6-[3-methoxyestra-1,3,5(10)trien-6 alpha-yl]deoxyadenosine (identified as a base adduct) were identified using HPLC by comparing them with authentic specimens prepared by reacting dG; and dA with both sulfates. No steroid-dC adduct was detected in the digestion products of the DNA adduct, although dC reacted with the sulfates to form N-4-[3-methoxyestra-1,3,5(10)-trien-G beta-yl] deoxycytidine, These results mean that estrogen B-sulfate has an ability to modify DNA via the amino group of a guanine or adenine residue in DNA. The present studies imply that a sequential metabolism (hydroxylation and sulfation) at the Cs-position of the estrogen molecule causes damage to DNA.

  DOI：

  10.1021/tx9800957

文献信息

• Identification of Estrogen-Modified Nucleosides from Calf Thymus DNA Reacted with 6-Hydroxyestrogen 6-Sulfates
  作者：Shinji Itoh、Toshiaki Hirai、Yukari Totsuka、Hidetoshi Takagi、Yumiko Tashiro、Koji Wada、Keiji Wakabayashi、Shinya Shibutani、Itsuo Yoshizawa

  DOI：10.1021/tx9800957

  日期：1998.11.1

  Two estrogen sulfates, pyridinium 3-methoxyestra-1,3,5(10)-trien-6 alpha-yl sulfate (3MeE-6 alpha-S) and its GP-isomer (3MeE-6 beta-S), synthesized as model compounds to demonstrate the carcinogenesis of estrogen, were found to react with calf thymus DNA to produce steroid-modified DNA adducts. Digestion of the DNA by nuclease P1 and phosphodiesterase I followed by alkaline phosphatase gave a deoxyribonucleoside fraction, of which N-2-[3-methoxyestra-1,3,5( 10)-trien-6 alpha-yl]deoxyguanosine, N-2-[3-methoxyestra-1,3,5( 10)-trien-6 beta-yl]deoxyguanosine, N-6-[3-methoxyestra-1,3,5(10)-trien-6 alpha-yl]deoxyadenosine, and N-6-[3-methoxyestra-1,3,5(10)trien-6 alpha-yl]deoxyadenosine (identified as a base adduct) were identified using HPLC by comparing them with authentic specimens prepared by reacting dG; and dA with both sulfates. No steroid-dC adduct was detected in the digestion products of the DNA adduct, although dC reacted with the sulfates to form N-4-[3-methoxyestra-1,3,5(10)-trien-G beta-yl] deoxycytidine, These results mean that estrogen B-sulfate has an ability to modify DNA via the amino group of a guanine or adenine residue in DNA. The present studies imply that a sequential metabolism (hydroxylation and sulfation) at the Cs-position of the estrogen molecule causes damage to DNA.