1,4:3,6-二脱水-2-脱氧-5-O-硝基-2-哌啶-1-基-L-艾杜糖醇盐酸 | 73466-15-6

• 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
• 中文名称: 1,4:3,6-二脱水-2-脱氧-5-O-硝基-2-哌啶-1-基-L-艾杜糖醇盐酸
• 英文名称: D-S-nitroso-β,β-dimethylcysteine
• 英文别名: S-nitroso-N-acetylpenicillamine；S-nitroso-N-penicillamine；S-nitroso-penicillamine；S-nitrosopenicillamine；D-S-nitrosopenicillamine；(2S)-2-amino-3-methyl-3-nitrososulfanylbutanoic acid
• CAS: 73466-15-6
• 化学式: C₅H₁₀N₂O₃S
• 分子量: 178.212
• InChiKey: QLPXHECKUSZTMH-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-青霉胺 在 盐酸 、 二乙烯三胺五醋酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.25h， 生成 1,4:3,6-二脱水-2-脱氧-5-O-硝基-2-哌啶-1-基-L-艾杜糖醇盐酸
  参考文献：
  名称：

  Antimicrobial Activity of Nitric Oxide-Releasing Ti-6Al-4V Metal Oxide

  摘要：

  钛和钛合金材料常用于关节置换，因其具有高强度。病原微生物很容易粘附在金属植入物表面，导致植入物失效的风险增加。钛-铝-钒（Ti-6Al-4V）金属氧化物植入材料表面被功能化处理，以释放一种小分子抗菌物质——一氧化氮。S-亚硝基青霉胺是一种S-亚硝基硫醇型一氧化氮供体，通过自组装单层膜法共价固定在金属氧化物表面。红外光谱技术证实了S-亚硝基硫醇供体成功附着于Ti-Al-4V表面。S-亚硝基青霉胺的附着使材料在生理条件下释放出89.6 ± 4.8 nmol/cm²的一氧化氮（NO）。这种低浓度的一氧化氮分别使大肠杆菌和表皮葡萄球菌的生长减少了41.5 ± 1.2%和25.3 ± 0.6%。结合S-亚硝基硫醇释放的Ti-6Al-4V与常用抗生素四环素，能增加抗生素的效力达35.4 ± 1.3%，从而允许使用更低剂量的抗生素。S-亚硝基青霉胺修饰的Ti-6Al-4V与氨苄西林对表皮葡萄球菌未显示出协同效应。功能化处理的Ti-6Al-4V表面对小鼠成纤维细胞无细胞毒性。

  DOI：

  10.3390/jfb8020020

文献信息

• Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols
  作者：Kun Wang、Zhong Wen、Wei Zhang、Ming Xian、Jin-Pei Cheng、Peng George Wang

  DOI：10.1016/s0960-894x(00)00688-0

  日期：2001.2

  Using UV-vis spectrometrical measurements, equilibrium constants for NO transfer between S-nitroso-N-acetyl-penicillamine (SNAP) and different thiols as well as kinetic data for NO transfer from S-nitroso bovine serum albumin (BSANO) to thiols have been obtained, NO transfer from SNAP to other primary/secondary thiols are thermodynamically favorable, whereas other S-nitrosothiols exhibit similar NO transfer potential. The obtained Gibbs free energy, enthalpy and entropy data indicated that NO transfer reactions from SNAP to four thiols are exothermic with entropy loss. The kinetic behavior of BSANO/RSH transfer can be related to both the acidity of sulfhydryl group and the electronic structure in thiol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Mechanism-Based Triarylphosphine-Ester Probes for Capture of Endogenous RSNOs
  作者：Uthpala Seneviratne、Luiz C. Godoy、John S. Wishnok、Gerald N. Wogan、Steven R. Tannenbaum

  DOI：10.1021/ja401565w

  日期：2013.5.22

  Nitrosothiols (RSNOs) have been proposed as important intermediates in nitric oxide (NO center dot) metabolism, storage, and transport as well as mediators in numerous NO. signaling pathways. RSNO levels are finely regulated, and dysregulation is associated with the etiology of several pathologies. Current methods for RSNO quantification depend on indirect assays that limit their overall specificity and reliability. Recent developments of phosphine-based chemical probes constitute a promising approach for the direct detection of RSNOs. We report here results from a detailed mechanistic and kinetic study for trapping RSNOs by three distinct phosphine probes, including structural identification of novel intermediates and stability studies under physiological conditions. We further show that a triarylphosphine-thiophenyl ester can be used in the absolute quantification of endogenous GSNO in several cancer cell lines, while retaining the elements of the SNO functional group, using an LC-MS-based assay. Finally, we demonstrate that a common product ion (m/z = 309.0), derived from phosphine RSNO adducts, can be used for the detection of other low-molecular weight nitrosothiols (LMW-RSNOs) in biological samples. Collectively, these findings establish a platform for the phosphine ligation-based, specific and direct detection of RSNOs in biological samples, a powerful tool for expanding the knowledge of the biology and chemistry of NO center dot-mediated phenomena.
• Antimicrobial Activity of Nitric Oxide-Releasing Ti-6Al-4V Metal Oxide
  作者：Nina Reger、Wilson Meng、Ellen Gawalt

  DOI：10.3390/jfb8020020

  日期：——

  Titanium and titanium alloy materials are commonly used in joint replacements, due to the high strength of the materials. Pathogenic microorganisms can easily adhere to the surface of the metal implant, leading to an increased potential for implant failure. The surface of a titanium-aluminum-vanadium (Ti-6Al-4V) metal oxide implant material was functionalized to deliver an small antibacterial molecule, nitric oxide. S-nitroso-penicillamine, a S-nitrosothiol nitric oxide donor, was covalently immobilized on the metal oxide surface using self-assembled monolayers. Infrared spectroscopy was used to confirm the attachment of the S-nitrosothiol donor to the Ti-Al-4V surface. Attachment of S-nitroso-penicillamine resulted in a nitric oxide (NO) release of 89.6 ± 4.8 nmol/cm2 under physiological conditions. This low concentration of nitric oxide reduced Escherichia coli and Staphylococcus epidermidis growth by 41.5 ± 1.2% and 25.3 ± 0.6%, respectively. Combining the S-nitrosothiol releasing Ti-6Al-4V with tetracycline, a commonly-prescribed antibiotic, increased the effectiveness of the antibiotic by 35.4 ± 1.3%, which allows for lower doses of antibiotics to be used. A synergistic effect of ampicillin with S-nitroso-penicillamine-modified Ti-6Al-4V against S. epidermidis was not observed. The functionalized Ti-6Al-4V surface was not cytotoxic to mouse fibroblasts.

  钛和钛合金材料常用于关节置换，因其具有高强度。病原微生物很容易粘附在金属植入物表面，导致植入物失效的风险增加。钛-铝-钒（Ti-6Al-4V）金属氧化物植入材料表面被功能化处理，以释放一种小分子抗菌物质——一氧化氮。S-亚硝基青霉胺是一种S-亚硝基硫醇型一氧化氮供体，通过自组装单层膜法共价固定在金属氧化物表面。红外光谱技术证实了S-亚硝基硫醇供体成功附着于Ti-Al-4V表面。S-亚硝基青霉胺的附着使材料在生理条件下释放出89.6 ± 4.8 nmol/cm²的一氧化氮（NO）。这种低浓度的一氧化氮分别使大肠杆菌和表皮葡萄球菌的生长减少了41.5 ± 1.2%和25.3 ± 0.6%。结合S-亚硝基硫醇释放的Ti-6Al-4V与常用抗生素四环素，能增加抗生素的效力达35.4 ± 1.3%，从而允许使用更低剂量的抗生素。S-亚硝基青霉胺修饰的Ti-6Al-4V与氨苄西林对表皮葡萄球菌未显示出协同效应。功能化处理的Ti-6Al-4V表面对小鼠成纤维细胞无细胞毒性。