retinoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: retinoic acid
• 英文别名: retionic acid；(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic acid；(4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: SHGAZHPCJJPHSC-LJWFEXOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  retinoic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 retinoic acid chloride
  参考文献：
  名称：

  Stereospecific synthesis of retinoic acid glucoconjugates, as pseudo-substrates of epidermal β-glucocerebrosidase

  摘要：

  The synthesis of glucocerebrosides (precursors of skin lipids) analogues bearing the bioactive compound retinoic acid is described; the two diastereoisomeric gluco-conjugates glucose-glycerol-retinoic acid are pseudo-subtrates for the title enzyme. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00920-x
• 作为产物：
  描述：

  视黄醛 在 2,6-二氯靛酚 作用下， 以 aq. acetate buffer 为溶剂， 生成 retinoic acid
  参考文献：
  名称：

  Direct Comparison of the Enzymatic Characteristics and Superoxide Production of the Four Aldehyde Oxidase Enzymes Present in Mouse

  摘要：

  醛氧化酶（AOXs）是一种钼多黄酶类，在杂环化合物、脂肪族和芳香族醛的代谢和解毒过程中发挥着重要作用。这些酶使用氧作为终端电子受体，并在转化过程中产生还原氧。小鼠体内有四种不同的酶，即 mAOX1、mAOX3、mAOX4 和 mAOX2，它们是不同基因的产物。目前还从未对这四种酶的酶学特性和特征进行过直接和同时的比较。本报告在大肠杆菌中异源表达后，纯化了四种具有催化活性的 mAOX 酶。测定了四种小鼠 AOX 酶的动力学参数，并使用六种具有生理和毒理学意义的预测底物（即视黄醛、N 1-甲基烟酰胺、吡哆醛、香兰素、4-（二甲基氨基）肉桂醛（p- DMAC）和水杨醛）进行了比较。虽然视黄醛、香兰素、对二甲基氨基肉桂醛和水杨醛是四种小鼠 AOX 酶的有效底物，但 N 1-甲基烟酰胺不是 mAOX1 或 mAOX4 的底物，任何纯化的酶都不能代谢吡哆醛。总体而言，mAOX1、mAOX2、mAOX3 和 mAOX4 对活性底物的 KM 值和 kcat 值有显著差异。这四种小鼠 AOX 在产生超氧自由基的能力上也存在数量上的差异。关于最后一点，mAOX2 是产生超氧自由基速率最大的酶，与转化的底物摩尔数相比，约为 40%，而与人类酶同源的 mAOX1 在底物相同的情况下产生超氧自由基的速率约为 30%。

  DOI：

  10.1124/dmd.117.075937

文献信息

• Novel synthesis of acetylenes and polyenes via a desulfonylation reaction
  作者：Tadakatsu Mandai、Terumi Yanagi、Kunio Araki、Yoshihiro Morisaki、Mikio Kawada、Junzo Otera

  DOI：10.1021/ja00324a044

  日期：1984.6

  La presence d'un groupe acetoxy ou tetrahydropyrannyloxy en position β du groupe benzenesulfonyl conduit a la formation d'une liaison unique acetylenique ou polyenique donnant lieu a la formation de toute une variete de composes enyniques diyniques et polyeniques

  La Presence d'un groupe acetoxy ou tetrahydropyrannyloxy en position β du groupe bensulfonyl pipe a laformation d'une liaison unique 炔
• Potential Neuroprotective Drugs in Cerebral Ischemia: New Saturated and Polyunsaturated Lipids Coupled to Hydrophilic Moieties: Synthesis and Biological Activity
  作者：Alain César Biraboneye、Sébastien Madonna、Younes Laras、Slavica Krantic、Pamela Maher、Jean-Louis Kraus

  DOI：10.1021/jm900227u

  日期：2009.7.23

  The ganglioside GM1 has neuroprotective effects but is not of therapeutic value because of its lack of bioavailability. Thus, molecules that mimic GM I represent a novel approach to neuroprotection. We have synthesized 19 small GM1-like analogues whose simplified structure includes a hydrophobic saturated or unsaturated moiety linked to a hydrophilic moiety. We report their neuroprotective effects in two distinct models of nerve cell death using hippocampus-derived HT22 cells. We found that several analogues protected the HT22 cells from death at concentrations ranging from 2 to 5 mu M. Additional neuroprotective assays using cortical slices injured by glutamate confirmed these results. Since members of the MAP kinase family are known to be key players in nerve cell survival and death, we characterized the role of these kinases in the neuroprotective mechanisms of the GM1-like analogues. Interestingly, the results indicate that the compounds provide neuroprotection through distinct mechanisms of action.
• [EN] PHARMACEUTICAL COMPOSITION INCLUDING RETINOIC ACID AND CARBOHYDRATE AND USE THEREOF<br/>[FR] COMPOSITION PHARMACEUTIQUE COMPRENANT DE L'ACIDE RÉTINOÏQUE ET UN GLUCIDE ET SON UTILISATION
  申请人：[en]MASTERY BIOTECH CO., LTD.

  公开号：WO2023168608A1

  公开（公告）日：2023-09-14

  A pharmaceutical composition including a retinoic acid and a carbohydrate is provided. The pharmaceutical composition may further include a metal ion. Use of the pharmaceutical composition in the manufacture of a medicament for inhibiting infection or replication of a virus or for treating a cancer is also provided. The pharmaceutical composition can enhance the inhibition ability of virus infection and/or replication in comparison with the retinoic acid used only.
• Stereospecific synthesis of retinoic acid glucoconjugates, as pseudo-substrates of epidermal β-glucocerebrosidase
  作者：Daniel Redoulès、Jacques Perié

  DOI：10.1016/s0040-4039(99)00920-x

  日期：1999.6

  The synthesis of glucocerebrosides (precursors of skin lipids) analogues bearing the bioactive compound retinoic acid is described; the two diastereoisomeric gluco-conjugates glucose-glycerol-retinoic acid are pseudo-subtrates for the title enzyme. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Direct Comparison of the Enzymatic Characteristics and Superoxide Production of the Four Aldehyde Oxidase Enzymes Present in Mouse
  作者：Gökhan Kücükgöze、Mineko Terao、Enrico Garattini、Silke Leimkühler

  DOI：10.1124/dmd.117.075937

  日期：2017.8

  Aldehyde oxidases (AOXs) are molybdoflavoenzymes with an important role in the metabolism and detoxification of heterocyclic compounds and aliphatic as well as aromatic aldehydes. The enzymes use oxygen as the terminal electron acceptor and produce reduced oxygen species during turnover. Four different enzymes, mAOX1, mAOX3, mAOX4, and mAOX2, which are the products of distinct genes, are present in the mouse. A direct and simultaneous comparison of the enzymatic properties and characteristics of the four enzymes has never been performed. In this report, the four catalytically active mAOX enzymes were purified after heterologous expression in Escherichia coli . The kinetic parameters of the four mouse AOX enzymes were determined and compared with the use of six predicted substrates of physiologic and toxicological interest, i.e., retinaldehyde, N 1-methylnicotinamide, pyridoxal, vanillin, 4-(dimethylamino)cinnamaldehyde ( p- DMAC), and salicylaldehyde. While retinaldehyde, vanillin, p- DMAC, and salycilaldehyde are efficient substrates for the four mouse AOX enzymes, N 1-methylnicotinamide is not a substrate of mAOX1 or mAOX4, and pyridoxal is not metabolized by any of the purified enzymes. Overall, mAOX1, mAOX2, mAOX3, and mAOX4 are characterized by significantly different KM and kcat values for the active substrates. The four mouse AOXs are also characterized by quantitative differences in their ability to produce superoxide radicals. With respect to this last point, mAOX2 is the enzyme generating the largest rate of superoxide radicals of around 40% in relation to moles of substrate converted, and mAOX1, the homolog to the human enzyme, produces a rate of approximately 30% of superoxide radicals with the same substrate.

  醛氧化酶（AOXs）是一种钼多黄酶类，在杂环化合物、脂肪族和芳香族醛的代谢和解毒过程中发挥着重要作用。这些酶使用氧作为终端电子受体，并在转化过程中产生还原氧。小鼠体内有四种不同的酶，即 mAOX1、mAOX3、mAOX4 和 mAOX2，它们是不同基因的产物。目前还从未对这四种酶的酶学特性和特征进行过直接和同时的比较。本报告在大肠杆菌中异源表达后，纯化了四种具有催化活性的 mAOX 酶。测定了四种小鼠 AOX 酶的动力学参数，并使用六种具有生理和毒理学意义的预测底物（即视黄醛、N 1-甲基烟酰胺、吡哆醛、香兰素、4-（二甲基氨基）肉桂醛（p- DMAC）和水杨醛）进行了比较。虽然视黄醛、香兰素、对二甲基氨基肉桂醛和水杨醛是四种小鼠 AOX 酶的有效底物，但 N 1-甲基烟酰胺不是 mAOX1 或 mAOX4 的底物，任何纯化的酶都不能代谢吡哆醛。总体而言，mAOX1、mAOX2、mAOX3 和 mAOX4 对活性底物的 KM 值和 kcat 值有显著差异。这四种小鼠 AOX 在产生超氧自由基的能力上也存在数量上的差异。关于最后一点，mAOX2 是产生超氧自由基速率最大的酶，与转化的底物摩尔数相比，约为 40%，而与人类酶同源的 mAOX1 在底物相同的情况下产生超氧自由基的速率约为 30%。