S-(2,4-dinitrophenyl)glutathione | 26289-39-4

• 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: S-(2,4-dinitrophenyl)glutathione
• 英文别名: S-DNP-Glutathione；2-amino-5-[[1-(carboxymethylamino)-3-(2,4-dinitrophenyl)sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 26289-39-4
• 化学式: C₁₆H₁₉N₅O₁₀S
• 分子量: 473.42
• InChiKey: FXEUKVKGTKDDIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212° dec.
• 沸点：
  895.1±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)
• 溶解度：
  水：微溶

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  276
• 氢给体数：
  5
• 氢受体数：
  12

安全信息

• 储存条件：
  -20°C

制备方法与用途

(2,4-二硝基苯基)谷胱甘肽既是谷胱甘肽-S-转移酶的底物，也可用作不可逆的谷胱甘肽还原酶抑制剂，其Ki值为30µM。

反应信息

• 作为产物：
  描述：

  4-[(Z)-(2,4-二硝基苯氧基)-氧偶氮基]-1-哌嗪羧酸乙酯 在 glutathione-S-transferase 、 glutathion 、 d(TTTTTTTTAGGATCATGGTGATGCTCTACGTGCCGTAGCCTTTTTTTTT) 、 calcium chloride 、 magnesium chloride 作用下， 反应 0.17h， 生成 N-哌嗪甲酸乙酯 、 S-(2,4-dinitrophenyl)glutathione
  参考文献：
  名称：

  Protein–Protein Communication and Enzyme Activation Mediated by a Synthetic Chemical Transducer

  摘要：

  The design and function of A synthetic "chemical transducer" that can generate an unnatural communication channel between two proteins is described. Specifically, we show how this transducer enables platelet-derived growth factor to trigger (in vitro) the catalytic activity of glutathione-s-transferase (GST), which is not Its natural enzyme partner. GST activity can be further controlled by adding specific oligonucleotides that switch the enzymatic reaction: on and off: We also demonstrate that a molecular machine, which can regulate the function of an enzyme, could be used to change the way a prodrug is activated in a "programmable" manner.

  DOI：

  10.1021/jacs.5b01123

文献信息

• [1,2,4]-Dithiazoli(di)ne derivatives, inducers of gluthathione-S-transferase and NADPH quinone oxido-reductase, for prophylaxis and treatment of adverse conditions associated with cytotoxicity in general and apoptosis in particular
  申请人：Feenstra W. Roelof

  公开号：US20060194846A1

  公开（公告）日：2006-08-31

  The present invention relates to 5-imino-5H-[1,2,4]-dithiazol-3-yl-amine and [1,2,4]-dithiazolidine-3,5-diylidene-diamine derivatives as inducers of gluthathione-S-transferase (GST) and NADPH quinone oxidoreductase (NQO), to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said [1,2,4]-dithiazoli(di)ne derivatives. The invention also relates to the use of a compound disclosed herein for the treatment of adverse conditions associated with cytotoxicity in general and apoptosis in particular. The invention relates to compounds of the general formula (I): wherein wherein the symbols have the meanings given in the specification.

  本发明涉及5-亚胺-5H-[1,2,4]-二噻唑-3-基胺和[1,2,4]-二噻唑烷-3,5-二亚胺基二胺衍生物作为谷胱甘肽-S-转移酶（GST）和NADPH醌氧化还原酶（NQO）的诱导剂，涉及这些化合物的制备方法以及用于合成所述[1,2,4]-二噻唑（二）烷衍生物的新中间体。本发明还涉及使用本发明披露的化合物治疗与细胞毒性和特别是凋亡相关的不良状况。本发明涉及以下通式（I）的化合物： 其中符号的含义如说明书中所给。
• Metallkomplexe mit biologisch wichtigen Liganden, CLXI [1]. Halbsandwich-Komplexe mit tert-Leucin, Dipeptiden, Pentaglycin und Glutathion als Liganden / Metal Complexes with Biologically Important Ligands, CLXI [1]. Halfsandwich Complexes with tert-Leucine, Dipeptides, Pentaglycine and Glutathione
  作者：Winfried Hoffmüller、Harald Dialer、Wolfgang Beck

  DOI：10.1515/znb-2005-1211

  日期：2005.12.1

  Reactions of L-tert-Leucine (tert-butylglycine), tert-leucine methyl ester, GlyValOMe, and Leu- AlaOMe with the chloro-bridged complexes [Cp*IrCl₂]₂, [(p-cymene)RuCl₂]₂ or [(C₆Me₆)RuCl₂]₂ in the presence of NaOMe give the complexes [Cp*Ir(Cl)NH₂CH(R)CO₂] (1), [(p-cymene)Ru(Cl)- NH₂CH(R)CO₂] (2), Cp*Ir(Cl₂)[NH₂CH(R)CO₂Me] (5), (C₆Me₆)Ru(Cl)[NH₂CH₂CONHCH(R)- CO₂Me]}⁺Cl⁻ (6), [Cp*Ir(Cl)NH₂CH₂CONCH(R)CO₂Me] (7), [Cp*Ir(Cl)NH₂CH(CH₂CHMe₂)- CONCH(R)CO₂Me)] (8), and Cp*Ir(Cl₂)[NH₂CH₂CONHCH(R)CO₂Me) (9).

  With pentaglycine the complexes [Cp*Ir(Cl₂)(pentaglycinate⁺Na⁺)] (10) and [(C₆Me₆)Ru(pentaglycineOMe- H⁺)] (11) could be isolated. Coordination of one equivalent of the S-protected tripeptide glutathione to [Cp*Ir(Cl)] and to [(C₆Me₆)Ru(Cl)] was observed. Some in situ prepared (p-cymene)Ru complexes with deprotonated dipeptide esters were tested as catalysts and the complex [(p-cymene)Ru(Cl)(NH₂CH(CHMeEt)NCH (CHMe₂)CO₂tert-Bu)] gave a yield of 73% and moderate entantiomeric excess (36% ee) in the transfer hydrogenation of acetophenone to 2-propanol.

  L-叔-亮氨酸（叔丁基甘氨酸）、叔亮氨酸甲酯、GlyValOMe 和 Leu-AlaOMe 与氯桥联配合物 [Cp*IrCl₂]₂、[(p-环己烯)RuCl₂]₂ 或 [(C₆Me₆)RuCl₂]₂ 在 NaOMe 存在下反应，得到配合物 [Cp*Ir(Cl)NH₂CH(R)CO₂] (1)、[(p-环己烯)Ru(Cl)- NH₂CH(R)CO₂] (2)、Cp*Ir(Cl₂)[NH₂CH(R)CO₂Me] (5)、(C₆Me₆)Ru(Cl)[NH₂CH₂CONHCH(R)CO₂Me]}⁺Cl⁻ (6)、[Cp*Ir(Cl)NH₂CH₂CONCH(R)CO₂Me] (7)、[Cp*Ir(Cl)NH₂CH(CH₂CHMe₂)- CONCH(R)CO₂Me)] (8) 和 Cp*Ir(Cl₂)[NH₂CH₂CONHCH(R)CO₂Me) (9)。

  与五甘氨酸配合物 [Cp*Ir(Cl₂)(五甘氨酸盐⁺Na⁺)] (10) 和 [(C₆Me₆)Ru(五甘氨酸甲酯- H⁺)] (11) 可以被分离。观察到一等量 S-保护的三肽谷胱甘肽与 [Cp*Ir(Cl)] 和 [(C₆Me₆)Ru(Cl)] 的配位。一些原位制备的 (p-环己烯)Ru 配合物与去质子化的二肽酯作为催化剂，复合物 [(p-环己烯)Ru(Cl)(NH₂CH(CHMeEt)NCH (CHMe₂)CO₂叔丁基)] 在苯乙酮转移氢化为异丙醇中产率为73%，对映选择性中等（36% ee）。

• [EN] MOLECULAR SENSOR AND METHODS OF USE THEREOF<br/>[FR] CAPTEUR MOLÉCULAIRE ET SES PROCÉDÉS D'UTILISATION
  申请人：YEDA RES & DEV

  公开号：WO2014102803A1

  公开（公告）日：2014-07-03

  The present invention is directed to fluorescent molecular sensor based on thiazole orange as represented below for protein detection. Interaction of the protein target with the molecular sensors of this invention results in a significant increase in the fluorescence emission. The generation of light output signal enables one to detect protein biomarkers associated with different diseases or detecting the protein of interest also in living cells.

  本发明涉及一种基于噻唑橙的荧光分子传感器，用于蛋白质检测。本发明的分子传感器与蛋白质靶标的相互作用导致荧光发射显著增加。光输出信号的产生使得可以检测与不同疾病相关的蛋白生物标志物，或者在活细胞中检测感兴趣的蛋白质。
• Synthesis and PMR properties of some dehydroalanine derivatives
  作者：R.S. Asquith、P. Carthew

  DOI：10.1016/0040-4020(72)88085-2

  日期：1972.1

  number of new β-N-alkylamino acids have been synthesised from N-acetyldehydroalanine, and their chromatographic and PMR properties examined. A selected peptide S-DNP-glutathione has also been subjected to alkaline degradation and the formation of dehydroglutathione has been shown by PMR.

  由N-乙酰基脱氢丙氨酸合成了许多新的β- N-烷基氨基酸，并检查了它们的色谱和PMR特性。所选的肽S -DNP-谷胱甘肽也已经进行了碱性降解，并且脱氢谷胱甘肽的形成已经通过PMR显示。
• A General Supramolecular Approach to Regulate Protein Functions by Cucurbit[7]uril and Unnatural Amino Acid Recognition
  作者：Wenbing Cao、Xuewen Qin、Yong Wang、Zhen Dai、Xianyin Dai、Haoyu Wang、Weimin Xuan、Yingming Zhang、Yu Liu、Tao Liu

  DOI：10.1002/anie.202100916

  日期：2021.5.10

  Regulation of specific protein function is of great importance for both research and therapeutic development. Many small or large molecules have been developed to control specific protein function, but there is a lack of a universal approach to regulate the function of any given protein. We report a general host–guest molecular recognition approach involving modification of the protein functional surfaces

  特定蛋白质功能的调节对于研究和治疗开发都非常重要。已经开发了许多小分子或大分子来控制特定的蛋白质功能，但缺乏一种通用的方法来调节任何给定蛋白质的功能。我们报告了一种通用的主客体分子识别方法，涉及用遗传编码的非天然氨基酸修饰蛋白质功能表面，这些氨基酸带有可以被葫芦 [7] uril 特异性识别的客体侧链。使用两种酶和一种细胞因子作为模型，我们发现带有非天然氨基酸的蛋白质的活性可以通过宿主分子结合而关闭，从而阻断了其功能性结合表面。蛋白质活性可以通过用竞争性客体分子处理来恢复。