3-碘甲腺乙酸 | 60578-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-碘甲腺乙酸
• 中文别名: 4-(4-羟基苯氧基)-3-碘苯乙酸
• 英文名称: 3-iodothyroacetic acid
• 英文别名: 3-Iodothyroacetic acid；2-[4-(4-hydroxyphenoxy)-3-iodophenyl]acetic acid
• CAS: 60578-17-8
• 化学式: C₁₄H₁₁IO₄
• 分子量: 370.143
• InChiKey: JDBDXSUPAYTFGB-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-碘甲腺乙酸 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 生成 4-(4-Hydroxy-phenoxy)-3-iod-phenethylalkohol
  参考文献：
  名称：

  降胆固醇药。胸烷醇。

  摘要：

  DOI：

  10.1021/jm00328a013
• 作为产物：
  描述：

  1-(4-氯甲基-2-碘-苯氧基)-4-甲氧基-苯 在 sodium hydroxide 、 乙醇 、 乙二醇甲醚 、 氢碘酸 、 溶剂黄146 作用下， 生成 3-碘甲腺乙酸
  参考文献：
  名称：

  Roche et al., Bulletin de la Societe Chimique de France, 1959, p. 715

  摘要：

  DOI：

文献信息

• [EN] SYNTHETIC ANALOGUES OF 3-IODOTHYRONAMINE (T1AM) AND USES THEREOF<br/>[FR] ANALOGUES SYNTHÉTIQUES DE 3-IODOTHYRONAMINE (TIAM) ET UTILISATIONS DESDITS ANALOGUES
  申请人：UNIV PISA

  公开号：WO2015151068A1

  公开（公告）日：2015-10-08

  Novel synthetic analogues of 3-iodothyronamine of formula (I), pharmaceutical compositions containing the same, and medical uses thereof are described.

  描述了公式（I）的新型合成类似物3-碘甲状腺胺，以及含有该类似物的药物组合物和其医学用途。
• 3-Iodothyronamine reduces insulin secretion in vitro via a mitochondrial mechanism
  作者：Ina Lehmphul、Carolin S. Hoefig、Josef Köhrle

  DOI：10.1016/j.mce.2017.07.026

  日期：2018.1

  Purpose: 3-iodothyronamine (3-T(1)AM), a decarboxylated and deiodinated thyroid hormone metabolite, leads at pharmacological doses to hypoinsulinemia, hyperglucagonemia and hyperglycemia in vivo. As the pancreatic Langerhans islets express thyroid hormone transmembrane transporters (THTT), we tested the hypothesis that not only plasma membrane-mediated 3-T(1)AM binding to and activation of G-protein coupled receptors, but also 3-T(1)AM metabolite(s) generated by 3-T(1)AM uptake and metabolism might decrease glucose-stimulated insulin secretion (GSIS).Methods: Murine pancreatic beta-cells MIN6 were characterized for gene expression of THTT, deiodinases and monoamine oxidases. 3-T(1)AM uptake and intracellular metabolism to the corresponding 3-iodothyroacetic acid were analysed by liquid-chromatography tandem mass spectrometry (LC-MS/MS) at different time points in cells as well as the conditioned medium. Mitochondria( activity, especially ATP-production, was monitored real-time after 3-T(1)AM application using Seahorse Bioanalyzer technique. Effect of 3-T(1)AM on GSIS into the culture medium was assayed by ELISA.Results: MIN6 cells express classical THTT, proposed to transport 3-T(1)AM, as well as 3-T(1)AM metabolizing enzymes comparable to murine primary pancreatic islets. 3-T(1)AM accumulates in MIN6 cells and is metabolized by intracellular MaoB to 3-iodothyroacetic, which in turn is rapidly exported. 3-T(1)AM decreases mitochondrial ATP-production concentration dependently. GSIS is diminished by 3-T(1)AM treatment. Using LC-MS/MS, no further 3-T(1)AM metabolites except 3-iodothyroacetic were detectable.Conclusions: This data provides a first link between cellular 3-T(1)AM uptake and regulation of mitochondrial energy metabolism in beta-cells, resulting in reduced insulin secretion. We conclude that MIN6 is an appropriate cell model to study 3-T(1)AM-dependent (intra-)cellular biochemical mechanisms affecting insulin production in vitro. (C) 2017 Elsevier B.V. All rights reserved.