5,5'-二羟基-4,4'-联色胺 | 108535-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5,5'-二羟基-4,4'-联色胺
• 中文别名: 4,4'-二(吡咯烷乙酰基)联苯基二氢溴化
• 英文名称: 5,5'-dihydroxy-4,4'-bitryptamine
• 英文别名: 4,4'-bi(5-hydroxytryptamine)；3-(2-aminoethyl)-4-[3-(2-aminoethyl)-5-hydroxy-1H-indol-4-yl]-1H-indol-5-ol
• CAS: 108535-01-9
• 化学式: C₂₀H₂₂N₄O₂
• 分子量: 350.42
• InChiKey: KEVPJLBSMTXTHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  124
• 氢给体数：
  6
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  5-羟基色胺 在 hemin 、 双氧水 、 sodium ascorbate 作用下， 以 aq. phosphate buffer 为溶剂， 反应 2.0h， 生成 5,5'-二羟基-4,4'-联色胺
  参考文献：
  名称：

  金属泰萨菲林作为 MRI 活性催化抗氧化剂治疗神经退行性疾病：阿尔茨海默氏病的研究

  摘要：

  神经退行性变的复杂病因学继续阻碍开发有效疗法的努力。阐明导致神经退行性变的关键途径的新药物可能有助于增加我们的理解并可能导致治疗方法的改进。在这里，我们证明水溶性锰（II）泰克萨菲林（MMn）是一种合适的磁共振成像（MRI）造影剂，用于检测较大的淀粉样蛋白β结构。 MMn 的成像潜力是根据体外研究和通过 MRI 和 ICP-MS 对阿尔茨海默病线虫模型进行的体内检测推断的。基于体外抗氧化剂和细胞的测定为这样的观点提供了支持，即这种卟啉类似物有望作为一种治疗剂，能够减轻被认为是神经退行性疾病病因的氧化和硝化毒性作用。本报告标志着首次详细阐述了一种 MRI 活性金属抗氧化剂，无需结合放射性同位素、靶向部分或治疗有效负载，即可在阿尔茨海默病模型中提供诊断和治疗益处。

  DOI：

  10.1016/j.chempr.2019.12.016

文献信息

• Induced accumulation of tyramine, serotonin, and related amines in response to <i>Bipolaris sorokiniana</i> infection in barley
  作者：Atsushi Ishihara、Rie Kumeda、Noriko Hayashi、Yukari Yagi、Nanase Sakaguchi、Yu Kokubo、Naoki Ube、Shin-ichi Tebayashi、Kotomi Ueno

  DOI：10.1080/09168451.2017.1290520

  日期：2017.6.3

  The inducible metabolites were analyzed in barley leaves inoculated with Bipolaris sorokiniana, the causal agent of spot blotch of barley. HPLC analysis revealed that B. sorokiniana-infected leaves accumulated 4 hydrophilic compounds. They were purified by ODS column chromatography and preparative HPLC. Spectroscopic analyses revealed that they were tyramine (1), 3-(2-aminoethyl)-3-hydroxyindolin-2-one (2), serotonin (3), and 5,5′-dihydroxy-2,4′-bitryptamine (4). Among these, 2 and 4 have not been reported as natural products. They showed antifungal activity in an assay of inhibition of B. sorokiniana conidia germination, suggesting that they play a role in the chemical defense of barley as phytoalexins. The accumulation of 1–4 was examined also in the leaves of rice and foxtail millet. Rice leaves accumulated 2, 3, and 4, whereas foxtail millet leaves accumulated 3 and 4 in response to pathogen attack, suggesting the generality of accumulation of 3 and 4 in the Poaceae species.

  大麦叶子接种了大麦斑病病原菌Bipolaris sorokiniana后，可诱导代谢产物进行了分析。高效液相色谱分析表明，感染B. sorokiniana的叶子积累了4种亲水化合物。这些化合物经过ODS柱色谱和制备性高效液相色谱纯化。光谱分析表明它们是酪胺（1）、3-(2-氨乙基)-3-羟基吲哚-2-酮（2）、血清素（3）和5,5'-二羟基-2,4'-双色胺（4）。在这些化合物中，2和4尚未被报道为天然产物。它们在抑制B. sorokiniana分生孢子萌发的测定中表现出抗真菌活性，表明它们在大麦的化学防御中起着植物抗菌素的作用。1-4的积累也在水稻和狗尾草叶片中进行了检查。水稻叶片在受到病原体攻击时积累了2、3和4，而狗尾草叶片在响应病原体攻击时积累了3和4，表明3和4在禾本科物种中的积累具有普遍性。
• Further Insights into the Oxidation Chemistry of 5-Hydroxytryptamine
  作者：Monika Z. Wrona、Glenn Dryhurst

  DOI：10.1002/jps.2600771102

  日期：1988.11

  An important product of electrochemical oxidation of 5-hydroxytryptamine (5-HT) in acid solution is the purple compound tryptamine-4,5-dione (6). However, any attempt to concentrate a solution containing 6 causes it to disappear. The most important reaction of 6 is dimerization to give another purple compound 7,7'-bi-(5-hydroxytryptamine-4-one). Dione 6 can also apparently react with 2,4'-bi-5-hydroxytryptamine

  酸性溶液中5-羟基色胺（5-HT）电化学氧化的重要产物是紫色化合物色胺4,5-二酮（6）。但是，任何浓缩包含6的溶液的尝试都会使其消失。6的最重要反应是二聚，得到另一种紫色化合物7,7'-bi-（5-hydroxytryptamine-4-one）。二酮6也显然可以与2,4'-联-5-羟色胺反应，得到三聚体4- [7'-（色胺-4,5-二酮）]-2,4''-联-5-羟色胺。最后，5-HT的6种和其他氧化产物在浓缩步骤中反应，生成的似乎是三聚体或更高的低聚物。该低聚物尚未确定，但已显示其可分解，部分产生神经毒素5-羟基色胺-4,7-二酮。
• Influence of L-Cysteine on the Oxidation Chemistry of Serotonin
  作者：M.Z. Wrona、S. Singh、G. Dryhurst

  DOI：10.1006/bioo.1994.1035

  日期：1994.12

  L-Cysteine (CySH) intervenes in the normal electrochemically driven oxidation of 5-hydroxytryptamine (5-HT; serotonin) at physiological pH by scavenging the quinone imine proximate oxidation product of this indolic neurotransmitter to give 4-S-cysteinyl-5-hydroxy-tryptamine (4-S-CyS-5-HT). The latter cysteinyl conjugate is more easily electro-oxidized than 5-HT and, in the presence of free CySH, undergoes a complex series of reactions leading to 8-(2-aminoethyl)-1,2,3,5,6,9-hexahydro-5,9-dioxo-pyrrolo [3, 2-g] [1, 4] benzothiazine-2-carboxylic acid (20) and N-[7-[(2-amino-2-carboxyethyl) thio]-3-(2-aminoethyl)-1,4-dihydro-4-oxo-5H-indol-5-ylidene]-L-cysteine (4). CySH also reacts with another normal oxidation product of 5-HT, tryptamine-4,5-dione, to give 4 and 20. There is evidence that aberrant oxidative metabolism of 5-HT occurs in the brains of Alzheimer's Disease patients. In the event that such reactions occur in the cytoplasm of serotonergic nerve terminals or axons they would necessarily expose electrophilic intermediates and products to the intraneuronal nucleophiles CySH and GSH. The results of this study indicate that 4 and 20 might represent aberrant oxidative metabolites formed in such reactions. However, the ease of oxidation of 4-S-CyS-5-HT compared to 5-HT suggest that this conjugate is likely to be only a transient species in vivo under conditions where the neurotransmitter is oxidized. (C) 1994 Academic Press, Inc.
• Oxidation of Serotonin by Superoxide Radical:  Implications to Neurodegenerative Brain Disorders
  作者：Monika Z. Wrona、Glenn Dryhurst

  DOI：10.1021/tx970185w

  日期：1998.6.1

  Many new lines of evidence implicate both superoxide anion radical (O-2 .(-)) and biogenic amine neurotransmitters in the pathological mechanisms that underlie neuronal damage caused by methamphetamine (MA), glutamate-mediated oxidative toxicity, ischemia-reperfusion, and other neurodegenerative brain disorders. In this investigation the oxidation of 5-hydroxy-tryptamine (5-HT, serotonin) by an O-2 .(-)-generating system (xanthine/xanthine oxidase) in buffered aqueous solution at pH 7.4 has been studied. The major product of the O-2 .(-)-mediated oxidation of 5-HT is tryptamine-4,5-dione (T-4,5-D). However, O-2 .(-) and H2O2, cogenerated by the xanthine oxidase-mediated oxidation of xanthine to uric acid, together react with trace levels of iron that contaminate buffer constituents to give a chemically ill-defined ore-iron species. This species mediates the oxidation of 5-HT to a C(4)-centered carbocation intermediate that reacts with 5-HT to give 5,5'-dihydroxy-4,4'-bitryptamine (4,4'-D) and with uric acid to give 9-[3-(2-aminoethyl)-5-hydroxy-1H-indol-4-yl]-2,6, 8-triketo-1H, 3H, 7H-purine (7) as the major products. These products differ from those formed in the HO.-mediated oxidation of 5-HT under similar conditions. When the reaction is carried out in the presence of the intraneuronal nucleophile glutathione (GSH), T-4,5-D is scavenged to give 7-(S-glutathionyl)-tryptamine-4,5-dione, whereas the putative carbocation intermediate is scavenged to give 4-(S-glutathionyl)-5-hydroxytryptamine T-4,5-D also reacts with the sulfhydryl residues of a model protein, alcohol dehydrogenase, and inhibits its activity. Previous investigators have proposed that T-4,5-D is a serotonergic neurotoxin. This raises the possibility that T-4,5-D and perhaps other putative intraneuronal metabolites formed by the O-2 .(-)/H2O2/oxo-iron-mediated oxidations of 5-HT might be endotoxins that contribute to neurodegeneration in brain regions innervated by serotonergic neurons caused by MA, ischemia-reperfusion, and other neurodegenerative brain disorders.
• Artificial enzyme with magnetic properties and peroxidase activity on indoleamine metabolite tumor marker
  作者：Daniel Antuña-Jiménez、M. Carmen Blanco-López、Arturo J. Miranda-Ordieres、María Jesús Lobo-Castañón

  DOI：10.1016/j.polymer.2014.01.037

  日期：2014.3