methyl 12-formyldeoxycholate | 71781-51-6

• 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: methyl 12-formyldeoxycholate
• 英文别名: 12α-formyloxy-3α-hydroxy-5β-cholan-24-oic acid methyl ester；12α-Formyloxy-3α-hydroxy-5β-cholan-24-saeure-methylester
• CAS: 71781-51-6
• 化学式: C₂₆H₄₂O₅
• 分子量: 434.616
• InChiKey: ZDYHQEPGSXDQEK-VAYUFCLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 12-formyldeoxycholate 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 乙酰氯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基丙烯基脲 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 242.5h， 生成 24-methyl 3α-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino-12α-hydroxy-5β-cholanoate
  参考文献：
  名称：

  New fluorescent bile acids: Synthesis, chemical characterization, and disastereoselective uptake by Caco-2 cells of 3-deoxy 3-NBD-amino deoxycholic and ursodeoxycholic acid

  摘要：

  Deoxycholic acid (DCA), a secondary bile acid (BA), and ursodeoxycholic acid (UDCA), a tertiary BA, cause opposing effects in vivo and in cell suspensions. Fluorescent analogues of DCA and UDCA could help investigate important questions about their cellular interactions and distribution.We have prepared a set of isomeric 3 alpha- and 3 beta-amino analogues of UDCA and DCA and derivatised these with the discrete fluorophore, 4-nitrobenzo-2-oxa-1,3-diazol (NBD), forming the corresponding four fluorescent adducts. These absorb in the range 465-470 nm and fluoresce at approx. 535 nm.In order to determine the ability of the new fluorescent bile acids to mimic the parents, their uptake was studied using monolayers of Caco-2 cells, which are known to express multiple proteins of the organic anion-transporting peptide (OATP) subfamily of transporters. Cellular uptake was monitored over time at 4 and 37 degrees C to distinguish between passive and active transport.All four BA analogues were taken up but in a strikingly stereo-and structure-specific manner, suggesting highly discriminatory interactions with transporter protein(s). The alpha-analogues of DCA and to a lesser extent UDCA were actively transported, whereas the beta-analogues were not. The active transport process was saturable, with Michaelis-Menten constants for 3 alpha-NBD DCA (5) being K-m = 42.27 +/- 12.98 mu M and V-max = 2.8 +/- 0.4 nmol/(mg protein*min) and for 3 alpha-NBD UDCA (3) K-m = 28.20 +/- 7.45 mu M and V-max = 1.8 +/- 0.2 nmol/(mg protein(*)min). These fluorescent bile acids are promising agents for investigating questions of bile acid biology and for detection of bile acids and related organic anion transport processes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.002
• 作为产物：
  描述：

  去氧胆酸 在 盐酸 、 高氯酸 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 11.33h， 生成 methyl 12-formyldeoxycholate
  参考文献：
  名称：

  衍生自脱氧胆酸，鹅去氧胆酸和石胆酸的新型高毒性胆汁酸

  摘要：

  为了研究3-叠氮基和24-酰胺化双重取代的作用，我们制备了一组由23种DCA，鹅去氧胆酸（CDCA）和石胆酸（LCA）的BA衍生物组成的新研究小组，在我们以前的研究中，这些特征分别与细胞毒性有关工作。使用3- [4,5-二甲基噻唑-2-基] -2,5-二苯基四唑溴化物（MTT）分析研究了化合物对HT-1080和Caco-2细胞活力的影响。为了了解细胞死亡的机制，使用流式细胞仪对具有降低细胞活力的高潜力化合物进行了进一步研究。用低微摩尔IC 50鉴定了几种化合物降低Caco-2和HT1080细胞系中细胞活力的数值，使其成为迄今报道的最有效的BA细胞凋亡因子之一。没有证据表明总体疏水性和细胞毒性之间存在联系，这支持了BA诱导细胞死亡可能是结构特异性的观点。衍生自DCA的化合物通过凋亡导致细胞死亡。有一些证据表明所研究的两种细胞系之间的选择性可能是由于CD95 / FAS的表达不同所致。毒性更大

  DOI：

  10.1016/j.bmc.2013.11.029

文献信息

• Synthesis of 3-glucuronides of unconjugated and conjugated bile acids.
  作者：JUNICHI GOTO、KAZUHIKO SUZAKI、TOSHIO NAMBARA

  DOI：10.1248/cpb.28.1258

  日期：——

  The 3-glucuronides of unconjugated, glyco- and tauro-conjugated bile acids have been prepared by an unequivocal route. Among three synthetic routes leading to the desired compounds, a method involving glucuronidation of the p-nitrophenyl ester by means of the Koenigs-Knorr reaction and subsequent conversion of the activated ester into the glyco-and tauro-conjugates was found to be most suitable. The nuclear magnetic resonance spectral data for bile acid glucuronides and related compounds are tabulated.

  非结合胆汁酸、糖结合胆汁酸和牛磺结合胆汁酸的 3-葡萄糖醛酸苷是通过一种明确的途径制备出来的。在获得所需化合物的三种合成路线中，通过柯尼希斯-克诺尔（Koenigs-Knorr）反应对硝基苯酯进行葡萄糖醛酸化，然后将活化的酯转化为糖型和牛磺酸型共轭物的方法最为合适。胆汁酸葡萄糖醛酸和相关化合物的核磁共振光谱数据已列表。
• Steroid Acids and Their Transformation Products. II. Desulfurization of Thiol Esters of Desoxycholic Acid^1a
  作者：George B. Spero、A. Vern McIntosh、Robert H. Levin

  DOI：10.1021/ja01185a074

  日期：1948.5