sodium taurodeoxycholate | 1180-95-6

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机钠
• 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: sodium taurodeoxycholate
• 英文别名: taurodeoxycholic acid sodium salt；NaTDC；sodium;(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-(2-sulfoethyl)pentanimidate
• CAS: 1180-95-6
• 化学式: C₂₆H₄₄NO₆S*Na
• 分子量: 521.694
• InChiKey: YXHRQQJFKOHLAP-FVCKGWAHSA-M

物化性质

• 熔点：
  168 °C (dec.)(lit.)
• 比旋光度：
  33 º (c=3, water)
• 溶解度：
  H2O:0.5 Mat 20 °C，透明，无色至淡黄色
• 稳定性/保质期：
  如果按照规定使用和储存，则不会发生分解，没有已知的危险反应。请避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R37
• WGK Germany：
  3
• 海关编码：
  29242990
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉干燥处。确保工作环境中具有良好的通风或排气设施。

制备方法与用途

生物活性

Taurodeoxycholate sodium salt 是一种与胆盐相关的阴离子洗涤剂，常用于分离膜蛋白，包括线粒体内膜蛋白。牛磺脱氧胆酸盐（TDCA）能够抑制多种炎症反应。

反应信息

• 作为反应物：
  描述：

  sodium taurodeoxycholate 在 乙二胺四乙酸 、 chloylglycine hydrolase 、 2-巯基乙醇 作用下， 以 phosphate buffer 为溶剂， 反应 0.33h， 以100%的产率得到去氧胆酸
  参考文献：
  名称：

  Xanthomonas maltophilia CBS 897.97 as a source of new 7β- and 7α-hydroxysteroid dehydrogenases and cholylglycine hydrolase: Improved biotransformations of bile acids

  摘要：

  The paper reports the partial purification and characterization of the 7 beta- and 7 alpha-hydroxysteroid dehydrogenases (HSDH) and cholylglycine hydrolase (CGH), isolated from Xanthomonas maltophilia CBS 897.97. The activity of 7 beta-HSDH and 7 alpha-HSDH in the reduction of the 7-keto bile acids is determined. The affinity of 7 beta-HSDH for bile acids is confirmed by the reduction, on analytical scale, to the corresponding 7 beta-OH derivatives. A crude mixture of 7 alpha- and 7 beta-HSDH, in soluble or immobilized form, is employed in the synthesis, on preparative scale, of ursocholic and ursodeoxycholic acids starting from the corresponding 7 alpha-derivatives. On the other hand, a partially purified 7 beta-HSDH in a double enzyme system, where the couple formate/formate dehydrogenase allows the cofactor recycle, affords 6 alpha-fluoro-3 alpha, 7 beta-dihydroxy-5 beta-cholan-24-oic acid (6-FUDCA) by reduction of the corresponding 7-keto derivative. This compound is not obtainable by microbiological route. The efficient and mild hydrolysis of glycinates and taurinates of bile acids with CGH is also reported. Very promising results are also obtained with bile acid containing raw materials. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.10.002
• 作为产物：
  描述：

  牛磺酸 、 去氧胆酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 乙腈 、 叔丁醇 为溶剂， 以95%的产率得到sodium taurodeoxycholate
  参考文献：
  名称：

  甘氨酸和牛磺酸缀合的胆汁盐的连续流动合成和放大†

  摘要：

  胆汁酸的N-酰基酰胺化的多克规模方案甘氨酸 和 牛磺酸已在连续流处理条件下成功开发。选择中熊去氧胆酸 （UDCA）作为模型化合物， N-乙氧基羰基-2-乙氧基-1,2-二氢喹啉（EEDQ）作为凝结剂，采用了模块化的中反应器辅助流动装置来显着加快反应条件的优化和流动规模的合成。报告并讨论了以收率，在线纯化，分析以及为优化反应和大规模生产而实施的流量设置方面的结果。

  DOI：

  10.1039/c2ob25528f
• 作为试剂：
  描述：

  2-(1,3-dipalmitoylglyceryl)-3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid ester 在 水 、 sodium taurodeoxycholate 作用下， 以 水 、 乙腈 为溶剂， 生成 睾酮 、 2-glyceryl-3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid ester 、 rac-1-glyceryl-3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid ester
  参考文献：
  名称：

  睾酮-脂质偶联物的合成和体外降解

  摘要：

  睾酮-脂质偶联物是通过将药物与 1,3-二棕榈酰甘油通过琥珀酸与 4-（1,3-二棕榈酰-2-甘油）丁酸和 3-棕榈酰氧基-2-棕榈酰氧基甲基丙酸共价结合而获得的。与相应的双脱酰基衍生物相比，脂质在水性缓冲液和血浆中没有显着水解。与胰脂肪酶孵育主要产生双十酰基化合物，其与甘油单酯相当，随后缓慢释放睾酮。结论是脂质缀合物是胰脂肪酶的底物。然而，由于空间位阻，药物释放非常缓慢。

  DOI：

  10.1002/ardp.19953280313

文献信息

• Thermodynamics and structure of inclusion compounds of tauro- and glyco-conjugated bile salts and β-cyclodextrin
  作者：René Holm、Wei Shi、Rune A. Hartvig、Sune Askjær、Jens Christian Madsen、Peter Westh

  DOI：10.1039/b820487j

  日期：——

  The interaction between natural β-cyclodextrin and bile salts common in rat, dog and man, taurocholate, tauro-β-muricholate, taurodeoxycholate, taurochenodeoxycholate, glycocholate, glycodeoxycholate and glycochenodeoxycholate, was studied using isothermal titration calorimetry, and the structural differences in the interaction were investigated by 1H-ROESY NMR and molecular modeling. The β-cyclodextrin was selected based upon its frequent use in preformulation and drug formulation as oral excipients for the solubilization of drug substances with low aqueous solubility. All the investigated bile salts possessed affinity for the cyclodextrin, though with large variations in the stability constants. The variations in the enthalpic and entropic contributions to the overall Gibbs free energy and consequently the stability constants revealed differences in the binding mode between the investigated bile salts, i.e. the bile salts with a hydroxyl group on C12 interacted differently from the bile salts without this hydroxyl group. These observations were supported by both 1H-ROESY NMR and molecular modeling, which suggested binding on the D-ring in the steroid structure for the former and on the C-ring for the latter bile salts.

  采用等温滴定量热法研究了天然δ-环糊精与大鼠、狗和人体内常见的胆盐（牛胆酸盐、牛δ-臼胆酸盐、牛脱氧胆酸盐、牛酚脱氧胆酸盐、甘氨胆酸盐、甘氨脱氧胆酸盐和甘氨苯脱氧胆酸盐）之间的相互作用，并通过 1H-ROESY NMR 和分子建模研究了相互作用中的结构差异。之所以选择δ-环糊精，是因为它经常作为口服辅料用于制剂前和药物制剂中，以增溶水溶性较低的药物物质。所有研究的胆汁盐都与环糊精具有亲和性，但稳定性常数差异较大。总体吉布斯自由能的焓贡献和熵贡献的变化以及由此产生的稳定性常数揭示了所研究胆汁盐之间结合模式的差异，即 C12 上带有羟基的胆汁盐与不带羟基的胆汁盐的相互作用方式不同。这些观察结果得到了 1H-ROESY NMR 和分子建模的支持，前者认为与类固醇结构中的 D 环结合，后者认为与 C 环结合。
• Spectroscopic Investigation of the Interaction of the Anticancer Drug Mitoxantrone with Sodium Taurodeoxycholate (NaTDC) and Sodium Taurocholate (NaTC) Bile Salts
  作者：Mirela Enache、Ana Maria Toader、Victoria Neacsu、Gabriela Ionita、Madalin I. Enache

  DOI：10.3390/molecules22071079

  日期：——

  two bile salts, sodium taurodeoxycholate (NaTDC) and sodium taurocholate (NaTC). Ultraviolet-visible (UV-Vis) absorption and electron paramagnetic resonance (EPR) spectroscopy were used to quantify the interaction and to obtain information on the location of mitoxantrone in bile salt micelles. The presence of submicellar concentrations of both bile salts induces mitoxantrone aggregation and the extent

  目前工作的重点是研究抗癌药物米托蒽醌与两种胆盐、牛磺脱氧胆酸钠 (NaTDC) 和牛磺胆酸钠 (NaTC) 的相互作用。紫外-可见 (UV-Vis) 吸收和电子顺磁共振 (EPR) 光谱用于量化相互作用并获得有关米托蒽醌在胆盐胶束中位置的信息。两种胆汁盐的亚胶束浓度的存在会诱导米托蒽醌聚集，并且 NaTDC 中的药物聚集程度高于 NaTC。对于胶束胆汁盐浓度，米托蒽醌单体被包裹在胶束核心中。绑定常量，胶束/水分配系数以及结合和分配过程的相应热力学参数使用胆汁盐存在下单体吸光度的变化来估计。米托蒽醌对 NaTDC 的结合相互作用比 NaTC 胶束更强，而在所有研究温度下，NaTC 胶束的分配效率更高。热力学参数表明结合和分配过程都是自发的和熵控制的。光谱行为和热力学参数表明不同类型的米托蒽醌与 NaTDC 和 NaTC 胶束的相互作用受到胆盐胶束性质和结构差异的支持。而在所有研究温度下，NaTC
• [EN] METHOD FOR MASS-PRODUCING SODIUM TAURODEOXYCHOLATE<br/>[FR] PROCÉDÉ DE PRODUCTION EN MASSE DE TAURODÉSOXYCHOLATE DE SODIUM<br/>[KO] 소디움 타우로디옥시콜레이트의 대량 생산 방법
  申请人：[en]SEOUL NATIONAL UNIVERSITY R&DB FOUNDATION;[ko]서울대학교 산학협력단

  公开号：WO2022059948A1

  公开（公告）日：2022-03-24

  본 발명은 소디움 타우로디옥시콜레이트의 상업적 생산을 위하여 이소프로필 알코올을 이용하며, 배치 워싱(batch washing) 방식을 이용하여 분리, 정제하여 공정과정이 단순화되면서 부산물이 적고 불순도가 낮은 소디움 타우로디옥시콜레이트의 대량 생산 방법에 관한 것이다.
• Xanthomonas maltophilia CBS 897.97 as a source of new 7β- and 7α-hydroxysteroid dehydrogenases and cholylglycine hydrolase: Improved biotransformations of bile acids
  作者：Paola Pedrini、Elisa Andreotti、Alessandra Guerrini、Mariangela Dean、Giancarlo Fantin、Pier Paolo Giovannini

  DOI：10.1016/j.steroids.2005.10.002

  日期：2006.3

  The paper reports the partial purification and characterization of the 7 beta- and 7 alpha-hydroxysteroid dehydrogenases (HSDH) and cholylglycine hydrolase (CGH), isolated from Xanthomonas maltophilia CBS 897.97. The activity of 7 beta-HSDH and 7 alpha-HSDH in the reduction of the 7-keto bile acids is determined. The affinity of 7 beta-HSDH for bile acids is confirmed by the reduction, on analytical scale, to the corresponding 7 beta-OH derivatives. A crude mixture of 7 alpha- and 7 beta-HSDH, in soluble or immobilized form, is employed in the synthesis, on preparative scale, of ursocholic and ursodeoxycholic acids starting from the corresponding 7 alpha-derivatives. On the other hand, a partially purified 7 beta-HSDH in a double enzyme system, where the couple formate/formate dehydrogenase allows the cofactor recycle, affords 6 alpha-fluoro-3 alpha, 7 beta-dihydroxy-5 beta-cholan-24-oic acid (6-FUDCA) by reduction of the corresponding 7-keto derivative. This compound is not obtainable by microbiological route. The efficient and mild hydrolysis of glycinates and taurinates of bile acids with CGH is also reported. Very promising results are also obtained with bile acid containing raw materials. (c) 2005 Elsevier Inc. All rights reserved.
• Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts
  作者：Francesco Venturoni、Antimo Gioiello、Roccaldo Sardella、Benedetto Natalini、Roberto Pellicciari

  DOI：10.1039/c2ob25528f

  日期：——

  been successfully developed under continuous flow processing conditions. Selecting ursodeoxycholic acid (UDCA) as the model compound and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) as the condensing agent, a modular mesoreactor assisted flow set-up was employed to significantly speed up the optimization of the reaction conditions and the flow scale-up synthesis. The results in terms of yield

  胆汁酸的N-酰基酰胺化的多克规模方案甘氨酸 和 牛磺酸已在连续流处理条件下成功开发。选择中熊去氧胆酸 （UDCA）作为模型化合物， N-乙氧基羰基-2-乙氧基-1,2-二氢喹啉（EEDQ）作为凝结剂，采用了模块化的中反应器辅助流动装置来显着加快反应条件的优化和流动规模的合成。报告并讨论了以收率，在线纯化，分析以及为优化反应和大规模生产而实施的流量设置方面的结果。