3α-(succinoyloxy)-12α-hydroxy-5β-cholan-24-oic acid | 87826-98-0

• 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: 3α-(succinoyloxy)-12α-hydroxy-5β-cholan-24-oic acid
• 英文别名: 12α-hydroxy-3α-(3-carboxy-propionyloxy)-5β-cholanoic acid-(24)；12α-Hydroxy-3α-(3-carboxy-propionyloxy)-5β-cholansaeure-(24)；(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-(3-carboxypropanoyloxy)-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 87826-98-0
• 化学式: C₂₈H₄₄O₇
• 分子量: 492.653
• InChiKey: JVPOBDYNYZIHLF-CNZWOIIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3α-(succinoyloxy)-12α-hydroxy-5β-cholan-24-oic acid 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-羟基-10,13-二甲基-12-氧代-1,2,3,4,5,6,7,8,9,11,14,15,16,17-十四氢环戊烯并[a]菲-17-基]戊酸
  参考文献：
  名称：

  The Preparation of the Homologs of 3-Hydroxy-12-ketocholanic Acid

  摘要：

  DOI：

  10.1021/ja01244a015
• 作为产物：
  描述：

  benzyl 3α,12α-dihydroxy-5β-cholan-24-oate 在 4-二甲氨基吡啶 、 palladium on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0~55.0 ℃ 、101.33 kPa 条件下， 生成 3α-(succinoyloxy)-12α-hydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  肠道共生体通过次级胆汁酸生物合成途径缓解 MASH

  摘要：

  研究发现肠道微生物群在代谢功能障碍相关脂肪性肝炎（MASH）的进展中发挥着重要作用，但其机制尚未确定。在这里，通过开发基于点击化学的富集策略，我们鉴定了几种微生物衍生的胆汁酸，包括以前未表征的3-琥珀酰胆酸（3-sucCA），它与肝组织患者的肝损伤呈负相关。 -活检证实的代谢功能障碍相关的脂肪肝病（MAFLD）。通过筛选人类细菌分离株，我们确定了能够有效生产 3-sucCA 和 3-sucCA 的菌株。通过基于活性的蛋白质纯化和鉴定，我们鉴定了一种负责 3-sucCA 生物合成的酶，注释为 β-内酰胺酶。此外，我们发现 3-sucCA 是一种流明限制代谢物，可通过促进 的生长来缓解 MASH。总之，我们的数据提供了对肠道微生物群-肝脏轴的新见解，可用于增强 MASH 的管理。

  DOI：

  10.1016/j.cell.2024.03.034

文献信息

• �ber Steroide. 46. Mitteilung. Ein einfacher Abbau der Gallens�uren-Seitenkette zur Methylketonstufe IV. Der Abbau der 3?-Oxy-allo-cholans�ure und der 3?-Oxy-cholans�ure (Lithochols�ure)
  作者：Ch. Meystre、K. Miescher

  DOI：10.1002/hlca.19460290107

  日期：——
• Stanciu, Magdalena Cristina; Nichifor, Marieta; Simionescu, Bogdan C., Revue Roumaine de Chimie, 2009, vol. 54, # 11-12, p. 951 - 955
  作者：Stanciu, Magdalena Cristina、Nichifor, Marieta、Simionescu, Bogdan C.

  DOI：——

  日期：——
• Effects of Bcl-2 modulation with G3139 antisense oligonucleotide on human breast cancer cells are independent of inherent Bcl-2 protein expression
  作者：Kim N. Chi、Anne E. Wallis、Chow Hwee Lee、Daniel Lopez de Menezes、Jason Sartor、Wieslawa H. Dragowska、Lawrence D. Mayer

  DOI：10.1023/a:1017371013487

  日期：2000.10

  We have investigated the effects of transient Bcl-2 down-regulation induced by the Bcl-2 antisense oligodeoxynucleotide (ODN) G3139 (Genta Incorporated) in high Bcl-2 protein expressing, estrogen receptor (ER) positive MCF-7 and low Bcl-2 expressing, ER negative MDA435/LCC6 human breast cancer cells. Treatment with Bcl-2 antisense ODN in vitro caused > 80% reduction of Bcl-2 protein levels in a sequence specific manner for both cell lines. Maximum mRNA reduction was achieved within 24 h of the first antisense ODN exposure whereas full protein down-regulation required antisense exposure over 48 h. This Bcl-2 reduction was associated with 80-95% loss of viable cells compared to untreated cells. Similar cytotoxic effects were observed in both cell lines despite a nine-fold intrinsic difference in Bcl-2 protein expression suggesting that the relative degree of down-regulation of Bcl-2 is more important than the absolute reduction. Cell death associated with G3139 exposure exhibited properties indicative of apoptosis such as mitochondrial membrane depolarization and caspase activation. Combined treatment with G3139 and cytotoxic agents resulted in additive cytotoxicity in both cell lines. However, under most conditions studied, the direct cytotoxic activity of G3139 antisense was not synergistic with the cytotoxic agents. These results suggest that while Bcl-2 clearly constitutes an attractive therapeutic target due to its role in regulating apoptosis in breast cancer cells, additional mechanisms are important in the control of apoptosis arising from exposure to anticancer agents in vitro.
• Steroid keto hydroxy acids and their polybasic acid esters and method of preparing same
  申请人：SCHERING CORP

  公开号：US02445006A1

  公开（公告）日：1948-07-13