丹磺酰酰胺基乙基硫醇 | 5354-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 丹磺酰酰胺基乙基硫醇
• 中文别名: 丹西酰胺基乙硫醇
• 英文名称: 5-(dimethylamino)-N-(2-mercaptoethyl)naphthalene-1-sulfonamide
• 英文别名: Dansylamidoethyl Mercaptan；5-(dimethylamino)-N-(2-sulfanylethyl)naphthalene-1-sulfonamide
• CAS: 5354-61-0
• 化学式: C₁₄H₁₈N₂O₂S₂
• 分子量: 310.441
• InChiKey: NIZZMACEVFIQSD-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108°C
• 溶解度：
  可溶于氯仿（轻微）、乙酸乙酯（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  丹磺酰酰胺基乙基硫醇 在 亚硝酸 作用下， 以 甲醇 、 水 为溶剂， 生成 5-(dimethylamino)-N-(2-nitrososulfanylethyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  在 tris(2-carboxyethyl)phosphine immobilized on agarose beads 作用下， 以 aq. phosphate buffer 、 异丙醇 为溶剂， 反应 0.5h， 生成 丹磺酰酰胺基乙基硫醇
  参考文献：
  名称：

  Reduction with tris(2-carboxyethyl)phosphine (TCEP) enables the use of an S-sulphonate protecting group for thiol-mediated bioconjugation

  摘要：

  在此，我们展示了水亲和性S-磺酸酯基团作为传统硫醇保护基团的有效替代品，适用于后续的去保护-生物偶联反应，并且与生化样品的使用条件相兼容。

  DOI：

  10.1039/c3ra47407k

文献信息

• Macrolides with antibacterial activity
  申请人：——

  公开号：US20030212011A1

  公开（公告）日：2003-11-13

  The invention provides new macrolides antibiotics of formula I with improved biological properties and having the formula 1 wherein R 1 , R 2 and R 3 are as herein described.

  这项发明提供了具有改进生物学性质的新的式I的大环内酯类抗生素，并具有式1，其中R1、R2和R3如本文所述。
• Pharmacological evaluation of disulfiram analogs as antimicrobial agents and their application as inhibitors of fosB-mediated fosfomycin resistance
  作者：Alexandria D. Lewis、Taylor M. Riedel、Meredith B. A. Kesler、Melinda E. Varney、Timothy E. Long

  DOI：10.1038/s41429-022-00500-2

  日期：2022.3

  Disulfide analogs of the alcohol sobriety medication disulfiram (Antabuse®) were evaluated for antimicrobial activity. Structure-activity relationship analyses of MIC data obtained for methicillin-resistant Staphylococcus aureus (MRSA) and other pathogenic organisms revealed correlations between the lipophilicity and bulkiness of the substituents. Analogs conferring optimal anti-MRSA activity contained S-octyl disulfides and either N,N-dimethyl- or N-pyrrolidine dithiocarbamate substituents. Additional testing revealed that both disulfiram and its S-octyl derivative are capable of sensitizing S. aureus to the bactericidal effects of fosfomycin. Mechanistic studies established that the compounds decrease intracellular levels of the fosB cofactor bacillithiol through a thiol-disulfide exchange reaction. The increased fosfomycin susceptibility in S. aureus was thereby attributed to a depleted cellular bacillithiol pool available for inactivation by fosB.

  酒精戒断药物二硫仑（Antabuse®）的二硫化物类似物被评估其抗微生物活性。对耐甲氧西林金黄色葡萄球菌（MRSA）和其他致病生物的最低抑菌浓度（MIC）数据进行的结构活性关系分析显示，取代基的亲脂性和体积之间存在相关性。具有最佳抗MRSA活性的类似物含有S-辛基二硫化物和N,N-二甲基或N-吡咯烷二硫代氨基甲酸酯取代基。额外测试表明，二硫仑及其S-辛基衍生物均能使金黄色葡萄球菌对磷霉素的杀菌效果产生敏感性。机制研究表明，这些化合物通过硫醇-二硫键交换反应降低了胞内辅因子巴克利硫醇的水平。因此，金黄色葡萄球菌对磷霉素的增敏被归因于可用于fosB失活的细胞内巴克利硫醇池的耗竭。
• Emollient, humectant, and fluorescent α,β-unsaturated thiol esters for long-acting skin applications
  作者：Carmen Robinson、Rosemarie F. Hartman、Seth D. Rose

  DOI：10.1016/j.bioorg.2008.06.004

  日期：2008.12

  from conjugate addition to the unsaturated thiol esters were determined by NMR spectroscopy. In the case of the alpha,beta,gamma,delta-unsaturated (sorboyl) thiol ester, both the 1,4-addition product and the beta,gamma-unsaturated-1,6-addition product formed, followed by diadduct. An in vivo test of the fluorescent alpha,beta-unsaturated thiol ester showed that this compound persisted on skin for 3 weeks

  我们描述了其中润肤剂或保湿剂带有能够与角质层蛋白质中的亲核氨基酸反应的α，β-不饱和硫醇酯的化合物。这些化合物应作为皮肤的持久保湿剂。衍生的润肤剂为丙酸十八烷基酯，保湿剂为聚乙二醇。发现在加入催化量的有机碱氯仿中后，这些疏水性和亲水性化合物以及一种荧光的，含丹磺酰基的硫醇酯在几分钟之内即可与硫醇N-乙酰半胱胺反应。通过NMR光谱法确定了由共轭物加成到不饱和硫醇酯上而得到的产物的结构。对于α，β，γ，δ-不饱和（山梨酰基）硫醇酯，1,4-加成产物和β，形成γ-不饱和的1,6-加成产物，然后生成加合物。荧光α，β-不饱和硫羟酸酯的体内试验表明，该化合物在皮肤上可持续3周，而对于非结合性对照化合物则为6天。
• Multifunctional bioconjugation by Morita–Baylis–Hillman reaction in aqueous medium
  作者：Gai-Li Li、Karen Ka-Yan Kung、Lan Zou、Hiu-Chi Chong、Yun-Chung Leung、Ka-Hing Wong、Man-Kin Wong

  DOI：10.1039/c2cc17116c

  日期：——

  An efficient approach for modular assembly of multifunctional bioconjugates from oligosaccharides, peptides and proteins with fluorescent probes/affinity tags based on Morita–Baylis–Hillman (MBH) reaction in aqueous medium has been developed.

  已开发出一种高效的方法，可以在水相介质中基于Morita–Baylis–Hillman (MBH) 反应，将寡糖、肽和蛋白质与荧光探针/亲和标签进行模块化组装，形成多功能生物共轭物。
• Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection
  作者：Albert A. Lee、Yi-Chen S. Chen、Elisa Ekalestari、Sheng-Yang Ho、Nai-Shu Hsu、Tang-Feng Kuo、Tsung-Shing Andrew Wang

  DOI：10.1002/anie.201603921

  日期：2016.9.26

  by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy‐to‐perform, one‐pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB‐Glc‐Ent, it can selectively label Gram‐negative bacteria

  铁载体，如Enterobactin（Ent），是可以通过同源转运蛋白与铁一起选择性导入细菌的小分子。因此，铁载体缀合物是用于将功能性试剂递送到细菌中的有前途的策略。在这项工作中，我们提出了一种功能强大的单糖基化肠杆菌素（MGE）易于执行的一锅化学酶法合成方法。当将功能化的MGE与罗丹明荧光团缀合后可提供RhB-Glc-Ent，它可以选择性地标记利用Ent的革兰氏阴性细菌，包括一些大肠杆菌菌株和铜绿假单胞菌。霍乱弧菌利用线性化Ent的细菌，也可以被弱靶向。而且，该靶向在铁限制条件下有效，但在富铁条件下无效。我们的结果表明，RhB‐Glc‐Ent探针不仅对细菌菌株敏感，而且对环境中的铁状况也敏感。