2-hydroxymelatonin

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-hydroxymelatonin
• 英文别名: N-(2-(2-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)acetamide；N-[2-(2-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: CIEAUFSGHUWAMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2Z)-2-羟基亚胺-N-(4-甲氧基苯基)乙酰胺 在 盐酸 、 platinum(IV) oxide 、 硫酸 、 水 、 氢气 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 1,4-二氧六环 、 乙二醇乙醚 、 水 、 乙酸乙酯 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 10.5h， 生成 2-hydroxymelatonin
  参考文献：
  名称：

  一些2取代的褪黑激素衍生物的简单合成

  摘要：

  报道了一种使用对茴香胺作为起始原料合成某些2-取代的褪黑激素衍生物的简单策略。关键步骤是在适当的酸酐存在下，通过在Adams催化剂上氢化或在催化量的无水氯化镍（II）存在下用硼氢化钠进行化学选择性还原氰基。2-取代的褪黑激素衍生物以六到七个步骤从廉价的对茴香胺中以9-13％的总产率获得。 吲哚-褪黑激素衍生物-还原-药物化学

  DOI：

  10.1055/s-0030-1258361

文献信息

• Uses of melatonin in skin
  申请人：Slominski Andrzej

  公开号：US20070218023A1

  公开（公告）日：2007-09-20

  Melatonin, which can be produced in the skin, exerts a protective effect against damage induced by ultraviolet radiation (UVR). The present study investigated the effect of UVB, the most damaging component of UVR, on melatonin metabolism in HaCaT keratinocytes and in a cell-free system. Four metabolites were identified by HPLC and LC-MS: 6-hydroxymelatonin, AFMK, 2-hydroxymelatonin (the main intermediate between melatonin and AFMK) and 4-hydroxymelatonin. Concentrations of these photoproducts were directly proportional to UVR-dose and to melatonin substrate content, and their accumulation was time dependent. The UVR-dependent increase of AFMK and 2-hydroxymelatonin was also detected in keratinocytes, where it was accompanied by simultaneous consumption of intracellular melatonin. Of note, melatonin and its two major metabolites, 2-hydroxymelatonin and AFMK, were also detected in untreated keratinocytes, neither irradiated nor preincubated with melatonin. Thus, intracellular melatonin metabolism is enhanced under exposure to UVR. The additional biological activity of these individual melatonin metabolites increases the spectrum of potential actions of the recently identified cutaneous melatoninergic system.

  褪黑激素可以在皮肤中产生，对紫外辐射（UVR）引起的损伤具有保护作用。本研究调查了UVB对HaCaT角质细胞和无细胞系统中褪黑激素代谢的影响，UVB是UVR中最具破坏性的组分。通过HPLC和LC-MS鉴定了四种代谢产物：6-羟基褪黑激素、AFMK、2-羟基褪黑激素（褪黑激素和AFMK之间的主要中间体）和4-羟基褪黑激素。这些光产物的浓度与UVR剂量和褪黑激素底物含量成正比，它们的积累是时间依赖的。在角质细胞中也检测到AFMK和2-羟基褪黑激素的UVR依赖性增加，同时伴随着细胞内褪黑激素的消耗。值得注意的是，未经辐照或未预先孵育褪黑激素的角质细胞中也检测到褪黑激素及其两种主要代谢产物2-羟基褪黑激素和AFMK。因此，在UVR暴露下，细胞内褪黑激素代谢得到增强。这些单个褪黑激素代谢产物的额外生物活性扩大了最近发现的皮肤褪黑激素系统的潜在作用范围。
• Composition comprising melatonin or its derivatives with coenzyme Q10 and use thereof against ageing of the skin
  申请人：UNIVERSIDAD DE GRANADA

  公开号：US10092544B2

  公开（公告）日：2018-10-09

  The invention relates to a composition comprising melatonin, a metabolite or derivative thereof and coenzyme Q10 and to use thereof for the production of a pharmaceutical or cosmetic composition for the treatment of the skin, said composition potentiating the movement of both molecules into the mitochondrion and facilitating percutaneous absorption, in which both the melatonin and the CoQ10 can reach all of the strata of the skin.

  本发明涉及一种由褪黑素、其代谢物或衍生物和辅酶 Q10 组成的组合物，以及将其用于生产治疗皮肤的药物或化妆品组合物，所述组合物可促进两种分子进入线粒体并促进经皮吸收，其中褪黑素和辅酶 Q10 可到达皮肤的所有层。
• Molecular cloning of melatonin 2-hydroxylase responsible for 2-hydroxymelatonin production in rice (<i>Oryza sativa</i> )
  作者：Yeong Byeon、Kyoungwhan Back

  DOI：10.1111/jpi.12220

  日期：2015.4

  AbstractAlthough melatonin biosynthetic genes from plants have been cloned, the melatonin catabolism mechanisms remain unclear. To clone the genes responsible for melatonin metabolism, we ectopically expressed 35 full‐length cDNAs of rice 2‐oxoglutarate‐dependent dioxygenase (2‐ODD) in Escherichia coli and purified the corresponding recombinant proteins. In vitro 2‐ODD assays showed four independent 2‐ODD proteins that were able to catalyze melatonin into 2‐hydroxymelatonin, exhibiting melatonin 2‐hydroxylase (M2H). These M2H proteins had peak activities at pH 8.0 and 30°C. The Km ranged from 121 μm to 371 μm with the Vmax ranging from 1.7 to 18.5 pkat/mg protein, respectively. The M2H enzyme activities were dependent on cofactors such as α‐ketoglutarate, ascorbate, and Fe2+, similar to the 2‐ODD enzymes. M2H activity was inhibited by prohexadione‐Ca, an inhibitor of 2‐ODD, in a dose‐dependent manner. M2H activity was high in the roots of rice seedlings, concurrent with high transcription levels of 2‐ODD 21, suggesting that 2‐ODD 21 was a major gene for M2H activity. Analogous to the high M2H activity in the roots, 2‐hydroxymelatonin was found in large quantities in roots treated with melatonin. These results suggest that melatonin was metabolized into 2‐hydroxymelatonin by the M2H genes in plants, but the physiological significance of 2‐hydroxymelatonin remains to be examined in the future.
• COMPOSITION COMPRISING MELATONIN OR ITS DERIVATIVES WITH COENZYME Q10 AND USE THEREOF AGAINST AGEING OF THE SKIN
  申请人：Universidad de Granada

  公开号：EP2926800B1

  公开（公告）日：2019-05-29
• Simple Synthesis of Some 2-Substituted Melatonin Derivatives
  作者：Natalia Lozinskaya、Sergey Sosonyuk、Maria Volkova、Michael Seliverstov、Marina Proskurnina、Sergey Bachurin、Nikolay Zefirov

  DOI：10.1055/s-0030-1258361

  日期：2011.1

  synthesis of some 2-substituted melatonin derivatives using p-anisidine as starting material is reported. The key step is a chemoselective reduction of a cyano group in the presence of an appropriate acid anhydride by hydrogenation over Adams’ catalyst or with sodium borohydride in the presence of catalytic amounts of anhydrous nickel(II) chloride. The 2-substituted melatonin derivatives were obtained

  报道了一种使用对茴香胺作为起始原料合成某些2-取代的褪黑激素衍生物的简单策略。关键步骤是在适当的酸酐存在下，通过在Adams催化剂上氢化或在催化量的无水氯化镍（II）存在下用硼氢化钠进行化学选择性还原氰基。2-取代的褪黑激素衍生物以六到七个步骤从廉价的对茴香胺中以9-13％的总产率获得。 吲哚-褪黑激素衍生物-还原-药物化学