N-(N-acetyl-S-nitrosopenicillaminyl)-S-nitrosopenicillamine | 158945-00-7

• 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: N-(N-acetyl-S-nitrosopenicillaminyl)-S-nitrosopenicillamine
• 英文别名: N-Acetyl-3-(nitrososulfanyl)-L-valyl-3-(nitrososulfanyl)-L-valine；(2R)-2-[[(2R)-2-acetamido-3-methyl-3-nitrososulfanylbutanoyl]amino]-3-methyl-3-nitrososulfanylbutanoic acid
• CAS: 158945-00-7
• 化学式: C₁₂H₂₀N₄O₆S₂
• 分子量: 380.446
• InChiKey: LQRZMDYUFVUEFS-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  205
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-(N-acetyl-L-penicillaminyl)-L-penicillamine 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以40%的产率得到N-(N-acetyl-S-nitrosopenicillaminyl)-S-nitrosopenicillamine
  参考文献：
  名称：

  Moynihan, Humphrey A.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 797 - 806

  摘要：

  DOI：

文献信息

• Novel Polymers for Delivering nitric oxide in vivo
  申请人：——

  公开号：US20010020083A1

  公开（公告）日：2001-09-06

  Disclosed are novel polymers derivatized with at least one -SNO group per 1200 atomic mass unit of the polymer. In one embodiment, the S-nitrosylated polymer has stabilized —S—nitrosyl groups. In another embodiment the S-nitrosylated polymer prepared by polymerizing a compound represented by the following structural formula: 1 R is an organic radical. Each X′ is an independently chosen aliphatic group or substituted aliphatic group. Preferably, each X′ is the same and is a C2-C6 alkylene group, more preferably—CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —. p and m are independently a positive integer such that p+m is greater than two. The polymers of the present invention can be used to coat medical devices to deliver nitric oxide in vivo to treatment sites.

  本发明公开了每 1200 个原子质量单位的聚合物中至少含有一个 -SNO 基团的新型衍生聚合物。在一个实施方案中，S-亚硝基化聚合物具有稳定的-S-亚硝基基团。在另一个实施方案中，S-亚硝基化聚合物是通过聚合由以下结构式代表的化合物制备的： 1 R 是有机基。 每个 X′是独立选择的脂肪族基团或取代脂肪族基团。每个 X′最好是相同的 C2-C6 亚烷基，更优选-CH 2 -、-CH 2 -CH 2 -，-CH 2 CH 2 CH 2 - 或-CH 2 CH 2 CH 2 CH 2 -p 和 m 独立地为正整数，使得 p+m 大于 2。 本发明的聚合物可用于包裹医疗设备，将一氧化氮在体内输送到治疗部位。
• Stable NO-delivering compounds
  申请人：——

  公开号：US20010000039A1

  公开（公告）日：2001-03-15

  Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces.

  本发明公开了新型 NO 释放化合物，该化合物由稳定的 S-亚硝基和游离醇或游离硫醇基团组成。还公开了一种制备 NO 释放化合物的方法。该方法包括使聚硫醇或硫醇与亚硝基化剂反应。还公开了涂有所公开化合物的医疗器械、利用医疗器械将NO输送到受试者治疗部位的方法以及表面消毒的方法。
• High yield S-nitrosylation process
  申请人：——

  公开号：US20020062020A1

  公开（公告）日：2002-05-23

  A method for producing a S-nitrosylated species is provided. The method comprises: (a) providing a deoxygenated, alkaline aqueous solution comprising a thiol and a nitrite-bearing species; (b) acidifying the solution by adding acid to the solution while concurrently mixing the solution (e.g., by vigorously stirring the solution) to produce the S-nitrosylated species; and (c) isolating the S-nitrosylated species. The nitrite-bearing species can be, for example, an inorganic nitrite, such as an alkali metal nitrite, or an organic nitrite, such as an alkyl nitrite (e.g., ethyl nitrite, amyl nitrite, isobutyl nitrite or t-butyl nitrite). The thiol is preferably a thiol-containing polysaccharide, a thiol-containing lipoprotein, a thiol-containing amino acid or a thiol-containing protein, and more preferably a thiol-containing polysaccharide such as thiolated cyclodextrin. In many preferred embodiments, the S-nitrosylated species is insoluble in the acidified solution, precipitating upon formation. The S-nitrosylated species can be isolated, for example, by a process in which the precipitate is removed from the solution (e.g., by centrifugation) and the aqueous solvent remaining in the precipitate is sublimated (e.g., by freezing the precipitate and subjecting it to a vacuum). The isolated S-nitrosylated product is preferably protected from heat, light, moisture and oxygen.

  本发明提供了一种生产 S-亚硝基化物的方法。该方法包括：(a) 提供包含硫醇和亚硝酸盐的脱氧碱性水溶液；(b) 通过向溶液中添加酸来酸化溶液，同时搅拌溶液（例如，剧烈搅拌溶液）以产生 S-亚硝基化物；以及 (c) 分离 S-亚硝基化物。例如，含亚硝酸盐的物质可以是无机亚硝酸盐，如碱金属亚硝酸盐，或有机亚硝酸盐，如烷基亚硝酸盐（如亚硝酸乙酯、亚硝酸戊酯、亚硝酸异丁酯或亚硝酸叔丁酯）。硫醇优选为含硫醇的多糖、含硫醇的脂蛋白、含硫醇的氨基酸或含硫醇的蛋白质，更优选为含硫醇的多糖，如硫醇化的环糊精。在许多优选的实施方案中，S-亚硝基化物不溶于酸化溶液，在形成后沉淀。S 亚硝基化物可通过以下方法分离出来：例如，将沉淀从溶液中去除（如通过离心），然后将沉淀中残留的水溶剂升华（如通过冷冻沉淀并将其置于真空中）。分离出的 S-亚硝基化产物最好能避开热、光、湿气和氧气。
• Lipid-based nitric oxide donors
  申请人：Scimed Life Systems, Inc.

  公开号：US20020082221A1

  公开（公告）日：2002-06-27

  Novel nitric-oxide releasing lipid molecules are provided which comprise a lipid molecule selected from (a) phosphoglycerides, (b) lipids having a sphingosine base as a backbone, (c) monoacylglyerols, (d) diacylglycerols, (e) glycosylacylglycerols, and (f) sterol compounds of the formula: 1 where R is a branched aliphatic chain of eight or more carbon atoms, wherein the lipid molecule is provided with a nitric-oxide containing group which comprises (a) a—S—N═O moiety, (b) a—O—N═O moiety, or (c) a 2 moiety. Also provided are methods of forming such nitric oxide releasing lipid molecules. Various pharmaceutical compositions, topical liquids and drug delivery systems comprising the nitric-oxide releasing lipid molecules are also described. Further provided are methods for therapeutically administering nitric oxide to patients, methods of treating or preventing various conditions, methods for promoting wound healing and methods of reducing the cells present in an atherosclerotic lesion, which methods utilize the nitric-oxide releasing lipid molecules.

  本发明提供了可释放一氧化氮的新型脂质分子，它包括选自以下物质的脂质分子：(a) 磷酸甘油酯；(b) 以鞘磷脂基为骨架的脂质；(c) 单酰基甘油；(d) 二酰基甘油；(e) 糖基酰基甘油；(f) 式中的甾醇化合物： 1 其中 R 是由 8 个或更多碳原子组成的支链脂族链，脂质分子中含有含一氧化氮的基团，该基团包括 (a) 一个 S-N═O 分子，(b) 一个 O-N═O 分子，或 (c) 一个 2 分子。此外，还提供了形成这种释放一氧化氮的脂质分子的方法。 还描述了包含一氧化氮释放脂质分子的各种药物组合物、局部液体和给药系统。进一步提供了向患者治疗性施用一氧化氮的方法、治疗或预防各种疾病的方法、促进伤口愈合的方法和减少动脉粥样硬化病变中存在的细胞的方法，这些方法都利用了一氧化氮释放脂质分子。
• Novel polymers for delivering nitric oxide in vivo
  申请人：Duke University

  公开号：US20030078365A1

  公开（公告）日：2003-04-24

  Disclosed are novel polymers derivatized with at least one —SNO group per 1200 atomic mass unit of the polymer. In one embodiment, the S-nitrosylated polymer has stabilized —S-nitrosyl groups. In another embodiment the S-nitrosylated polymer prepared by polymerizing a compound represented by the following structural formula: 1 R is an organic radical. Each X′ is an independently chosen aliphatic group or substituted aliphatic group. Preferably, each X′ is the same and is a C2-C6 alkylene group, more preferably —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —. p and m are independently a positive integer such that p+m is greater than two. The polymers of the present invention can be used to coat medical devices to deliver nitric oxide in vivo to treatment sites.

  本发明公开了每 1200 个原子质量单位的聚合物中至少含有一个 -SNO 基团的新型衍生聚合物。在一个实施方案中，S-亚硝基化聚合物具有稳定的-S-亚硝基基团。在另一个实施方案中，S-亚硝基化聚合物是通过聚合由以下结构式代表的化合物制备的： 1 R 是有机基。 每个 X′是独立选择的脂肪族基团或取代脂肪族基团。最好每个 X′都是相同的 C2-C6 亚烷基，更优选 -CH 2 -、-CH 2 -CH 2 -，-CH 2 CH 2 CH 2 - 或-CH 2 CH 2 CH 2 CH 2 -. p 和 m 独立地为正整数，使得 p+m 大于 2。 本发明的聚合物可用于包裹医疗设备，将一氧化氮在体内输送到治疗部位。