[4-14C]-testosterone | 633-32-9

• 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: [4-14C]-testosterone
• 英文别名: Testosterone 4-C-14；(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 633-32-9
• 化学式: C₁₉H₂₈O₂
• 分子量: 290.419
• InChiKey: MUMGGOZAMZWBJJ-WLRIMQDWSA-N

物化性质

• 密度：
  1.122±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
• 熔点：
  154-155 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4-14C]-testosterone 生成 (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile
  参考文献：
  名称：

  JOHNSTON, D.;ELDER, D., J. LABELL. COMPOUNDS AND RADIOPHARM, 27,(1989) N 1, C. 9-16

  摘要：

  DOI：
• 作为产物：
  描述：

  [4-14C]-androsten-17β-(1,1-dimethylethoxy)-3-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以93%的产率得到[4-14C]-testosterone
  参考文献：
  名称：

  HIV复制的抑制：[4-14C]-5α-androstan-16α-bromo-3β-o1-17-one的合成

  摘要：

  描述了 [4-14C]-5α-Androstan-16α-bromo-3β-ol-17-one (1) 通过中间体 [4-14C] 睾酮 (8) 的有效合成。这种化合物靶向细胞代谢途径，对 HIV 病毒致病性的临床试验很有希望。版权所有 © 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1344(20001030)43:12<1149::aid-jlcr401>3.0.co;2-4

文献信息

• Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells – Identifying inhibitors of non-classical pathways producing the most potent androgen
  作者：Sophie Boutin、Jenny Roy、René Maltais、Donald Poirier

  DOI：10.1016/j.bmcl.2019.126783

  日期：2020.1

  testis, 5α-DHT could also be produced from 5α-androstane-3α,17β-diol (3α-diol), an almost inactive androgen, following non-classical pathways. We reported the chemical synthesis of non-commercially available [4-14C]-3α-diol from [4-14C]-T, and the development of a biological assay to identify inhibitors of the 5α-DHT formation from radiolabeled 3α-diol in LAPC-4 cell PC model. We measured the inhibitory

  5α-二氢睾丸激素（5α-DHT）对雄激素受体（AR）具有很大的亲和力，其与AR的结合促进了雄激素依赖性PC中前列腺癌细胞（PC）的增殖。5α-DHT主要由睾丸中的睾丸激素（T）合成，也可以通过非经典途径由几乎无活性的雄激素5α-雄烷3α，17β-二醇（3α-二醇）产生。我们报道了由[4-14C] -T合成的非商业性[4-14C]-3α-二醇的化学合成方法，并开发了一种生物测定方法以鉴定放射性标记的3α-二醇中5α-DHT形成的抑制剂。 LAPC-4单元PC型号。我们测量了5α-雄烷衍生物对5α-DHT形成的抑制力，并获得了最有效的化合物（IC50 = 1.2-14.1μM）的抑制曲线。最有效的抑制剂25（IC50 = 1。
• ACOSTA, C. K.;CESSAC, J. W.;RAO, PEMMARAJU N.;KIM, HYUN K., J. LABELL. COMPOUNDS AND RADIOPHARM., 28,(1990) N0, C. 1201-1212
  作者：ACOSTA, C. K.、CESSAC, J. W.、RAO, PEMMARAJU N.、KIM, HYUN K.

  DOI：——

  日期：——
• Characterization of stable human aromatase expressed in E. coli
  作者：Norio Kagawa、Hiroshi Hori、Michael R. Waterman、Shiro Yoshioka

  DOI：10.1016/j.steroids.2004.01.002

  日期：2004.4

  Aromatase (P450arom, CYP19) catalyzes the aromatization reaction that converts androgens to estrogens. Although human P450arom has been readily purified from placenta, its hydrophobic properties and instability has hampered detailed characterization. Utilizing a N-terminal replacement (MARQSFGRGKL, derived from CYP2C11), we successfully modified this unstable enzyme into stable forms. Based on a known polymorphism, we created two constructs, NmA264C and NmA264R having cysteine or arginine at position 264. The recombinant P450arom NmA264R was expressed in Escherichia coli (350-400 nmol/L culture) primarily by coexpression with molecular chaperones GroES/GroEL while NmA264C was expressed (240 nmol/L culture) only in the presence of chloramphenicol. Although NmA264C was recovered only in the membrane fraction, approximately 14% of NmA264R was recovered in the cytosolic fraction, suggesting that NmA264R is more hydrophilic than NmA264C. NmA264R was highly purified to the specific content 13.6 nmol P450/mg protein. Purified P450arom NmA264R converted androstenedione to estrone with V-max 12.4 nmol/(min nmol) and K-m 0.26 muM, and testosterone to estradiol with V-max 52.2 nmol/(min nmol) and K-m 10.9 muM. Because of the increased stability of NmA264R, we could unambiguously determine properties of human P450arom by optical and electron paramagnetic resonance spectroscopy. The purified protein was a typical low-spin form, which was converted to a high-spin form when androstenedione was added. The rhombicity of substrate-bound forms was higher than that reported for other P450s, an interesting characteristic of human P450arom. The highly stable and active P450arom, NmA264R sets the stope for detailed structure/function analyses of this important member of the P450 superfamily. (C) 2004 Elsevier Inc. All rights reserved.