S-propylmercapto-L-glutathione | 30543-59-0

• 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-propylmercapto-L-glutathione
• 英文别名: GSSP；S-propylmercaptoglutathione；H-gGlu-Cys(SPr)(SPr)-Gly-OH；(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(propyldisulfanyl)propan-2-yl]amino]-5-oxopentanoic acid
• CAS: 30543-59-0
• 化学式: C₁₃H₂₃N₃O₆S₂
• 分子量: 381.474
• InChiKey: RGNVWSYKJVPEEP-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  S-丙基丙烷-1-硫代亚磺酸盐 、 谷胱甘肽 以 水 为溶剂， 反应 2.0h， 生成 S-propylmercapto-L-glutathione
  参考文献：
  名称：

  A Tissue Homogenate Method To Prepare Gram-Scale Allium Thiosulfinates and Their Disulfide Conjugates with Cysteine and Glutathione

  摘要：

  The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).

  DOI：

  10.1021/jf4003818

文献信息

• Allicin-inspired thiolated fluoroquinolones as antibacterials against ESKAPE pathogens
  作者：Jordan G. Sheppard、Timothy E. Long

  DOI：10.1016/j.bmcl.2016.10.002

  日期：2016.11

  Thiolated fluoroquinolones were synthesized from ciprofloxacin and evaluated for antimicrobial activity against a panel of pathogenic bacteria. Gram-positive species including methicillin-resistant Staphylococcus aureus (MRSA) exhibited the highest level of increased sensitivity toward ciprofloxacin bound with a N-propylthio substituent. Evidence was found that the antibiotics form disulfides with

  由环丙沙星合成硫代氟喹诺酮类药物，并评估其对一组致病细菌的抗菌活性。包括耐甲氧西林的金黄色葡萄球菌（MRSA）在内的革兰氏阳性菌种对环丙沙星与N-丙硫基取代基结合的敏感性表现出最高水平。有证据表明，抗生素在细菌中形成具有低分子量硫醇的二硫键，并增强了胞浆中活性氧（ROS）的生成。归根结底，硫醇化氟喹诺酮类药物的抗MRSA活性增强归因于细胞通透性增加以及与胞质硫醇的反应，产生了无活性的二硫键代谢产物和母体环丙沙星作为DNA合成抑制剂。
• Cysteine and Glutathione Mixed-Disulfide Conjugates of Thiosulfinates: Chemical Synthesis and Biological Activities
  作者：Guodong Zhang、Bin Li、Chen-Hsien Lee、Kirk L. Parkin

  DOI：10.1021/jf9029354

  日期：2010.2.10

  The chemical syntheses of cysteine (CYS) and glutathione (GSH) mixed -disulfide conjugates (CySSR, GSSR, respectively) of mercapto residues representing most of the R groups of thiosulfinates (R = methyl, ethyl, propyl, and allyl) are described. Gram-scale conjugates were prepared as >98% pure preparations, with 80% reaction yield for each of the two seminal synthesis steps, with structures confirmed by H-1 NMR and high-resolution MS analyses. These conjugates are derivatives of thiosulfinates that may be evolved in processed foods, in the digestive tract, and through in vivo metabolism. The prepared conjugates were found to be able to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7), indicating they have potential cancer preventive and anti-inflammatory activities. Among the prepared conjugates, the allyl conjugates of CYS and GSH, S-allylmercaptocysteine (CySSA) and S-allylmercaptoglutathione (GSSA), showed the most potent activity regarding QR induction and NO production inhibition. The conjugates with saturated R groups were also active and conferred biological activity as cystine and oxidized glutathione exhibited no effects in these cellular assays.
• US8481284B2
  申请人：——

  公开号：US8481284B2

  公开（公告）日：2013-07-09
• [EN] PROCESS OF PREPARING CONJUGATES OF ALLIUM ORGANOSULFUR COMPOUNDS WITH AMINO ACIDS, PEPTIDES, AND PROTEINS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CONJUGUÉS DE COMPOSÉS ORGANOSOUFRÉS D'ALLIUM AVEC DES ACIDES AMINÉS, DES PEPTIDES, ET DES PROTÉINES
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2011044113A1

  公开（公告）日：2011-04-14

  Processes using Allium tissue homogenates and extracts in a simple and cost-effective manner to maximize the yields and recovery of thiosulfinates from Allium tissues and related organisms possessing alliinase, LF synthase and/or S-alk(en)yl-L-cysteine sulfoxides are disclosed.