3-碘类甲腺质-[D4] | 712349-95-6

• 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-碘类甲腺质-[D4]
• 英文名称: 3-Iodothyronamine
• 英文别名: thyronamine T₁AM；3-T₁AM；4-[4-(2-aminoethyl)-2-iodophenoxy]phenol
• CAS: 712349-95-6
• 化学式: C₁₄H₁₄INO₂
• 分子量: 355.175
• InChiKey: XIINYOJWNGOUPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-碘类甲腺质-[D4] 在 semicarbazid-sensitive aminoxidase 、 monoamine oxidase 作用下， 生成 3-碘甲腺乙酸
  参考文献：
  名称：

  3-Iodothyronamine reduces insulin secretion in vitro via a mitochondrial mechanism

  摘要：

  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.

  DOI：

  10.1016/j.mce.2017.07.026
• 作为产物：
  描述：

  4-(三异丙基硅烷基氧基)苯基基硼酸 在 吡啶 、 sodium tetrahydroborate 、 DL-dithiothreitol 、 四丁基氟化铵 、 copper diacetate 、 三乙胺 、 naphthalene-1,8-diselenol 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 3-碘类甲腺质-[D4]
  参考文献：
  名称：

  甲状腺激素和碘甲状腺素胺的仿生去碘化作用–结构-活性关系研究†

  摘要：

  哺乳动物的硒酶碘甲状腺素脱碘酶（DIOs）催化甲状腺激素（THs）的酪氨酰和酚环碘化作用，并在维持全身TH浓度中起重要作用。这些酶还接受脱羧甲状腺激素代谢物碘甲状腺素（TAMs）作为脱碘的底物。已显示基于萘的硒和/或含硫的小分子介导甲状腺激素及其代谢产物的区域选择性酪氨酰环去碘化。在此，我们报道了一系列用于甲状腺激素和碘代乙胺的碘化的周边取代的含硒萘衍生物的结构-活性关系研究。单晶X射线晶体学和77Se NMR光谱研究表明，分子内Se⋯X（X = N，O和S）相互作用在合成模拟物的脱碘酶活性中起重要作用。此外，已观察到萘基硒和/或含硫的合成脱碘酶模拟物对脱羧代谢物TAMs的酪氨酰环脱碘作用比THs慢，这是基于Se⋯I卤素键的强度进行了解释。由TH和TAM组成。

  DOI：

  10.1039/c6ob01375a

文献信息

• ORGANOSILICON CARRIERS FOR USE IN TREATING INFECTIONS AND/OR DISEASES CAUSED BY SARS VIRUSES
  申请人：Salama Zoser B.

  公开号：US20210346305A1

  公开（公告）日：2021-11-11

  A method for treating, attenuating or inhibiting an infection and/or disease associated with a SARS virus in a subject is provided that includes administering a pharmaceutical composition to the subject. The composition includes an organosilicone carrier with one or more active substances that block and/or inhibit an ACE2 receptor in a host cell of the subject, the spike protein of a SARS virus and/or internal components of a virion of the SARS virus.

  提供了一种治疗、减轻或抑制与SARS病毒相关的感染和/或疾病的方法，包括向受试者施用药物组合物。该组合物包括一种有机硅载体，其中含有一个或多个能够阻断和/或抑制受试者宿主细胞中ACE2受体、SARS病毒的刺突蛋白和/或SARS病毒病毒颗粒内部组分的活性物质。
• [EN] IONIC LIQUID SUPPORTED ORGANOTIN REAGENTS FOR THE MANUFACTURING OF RADIOPHARMACEUTICALS COMPOUNDS<br/>[FR] RÉACTIFS ORGANOSTANNIQUES SUPPORTÉS SUR LIQUIDE IONIQUE POUR LA PRODUCTION DE COMPOSÉS RADIOPHARMACEUTIQUES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2015104300A1

  公开（公告）日：2015-07-16

  The present invention relates to an ionic liquid supported organotin reagent of formula (I). The invention further relates to a process for manufacturing the ionic liquid supported organotin reagent of formula (I) and to a process for manufacturing an halogenated or radio-halogenated compound using compound of formula (I). The invention also relates to a device for implementing the halogenating process of the invention and to a kit comprising the compound of formula (I).

  本发明涉及一种式（I）的离子液体支持的有机锡试剂。该发明还涉及一种制备式（I）的离子液体支持的有机锡试剂的方法，以及使用式（I）的化合物制备卤代或放射卤代化合物的方法。该发明还涉及一种用于实施本发明的卤化过程的装置，以及包括式（I）化合物的试剂盒。
• [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。
• Uses of formulations of thyroid hormone antagonists and nanoparticulate forms thereof to increase chemosensivity and radiosensitivity in tumor or cancer cells
  申请人：Ordway Research Institute, Inc.

  公开号：EP2662079A1

  公开（公告）日：2013-11-13

  Disclosed are methods of increasing the chemosensitivity of normal and/or chemoresistant tumor or cancer cells using thyroid hormone antagonists and/or nanoparticulate or polymeric forms thereof. Also disclosed are methods of increasing radiosensitivity of normal and/or radioresistant tumor or cancer cells using thyroid hormone antagonists and/or nanoparticulate or polymeric forms thereof.

  公开了使用甲状腺激素拮抗剂和/或其纳米粒子或聚合物形式来增加正常和/或化疗耐药肿瘤或癌细胞的化疗敏感性的方法。还公开了使用甲状腺激素拮抗剂和/或其纳米粒子或聚合物形式来增加正常和/或放射治疗耐药肿瘤或癌细胞的放射敏感性的方法。
• Thyronamine derivatives and analogs and methods of use thereof
  申请人：Scanlan S. Thomas

  公开号：US20050096485A1

  公开（公告）日：2005-05-05

  Thyronamine derivatives and analogs, methods of using such compounds, and pharmaceutical compositions containing them are disclosed. Methods of preparing such compounds are also disclosed

  本发明揭示了甲状腺胺衍生物和类似物，使用这些化合物的方法，以及含有它们的制药组合物。还揭示了制备这些化合物的方法。