N-溴牛磺酸 | 52316-57-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: N-溴牛磺酸
• 英文名称: taurine bromamine
• 英文别名: N-bromotaurine；2-(bromoamino)ethanesulfonic acid
• CAS: 52316-57-1
• 化学式: C₂H₆BrNO₃S
• 分子量: 204.045
• InChiKey: USAWSWBIFACPGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  牛磺酸 在 次氯酸 、 sodium bromide 作用下， 生成 N-溴牛磺酸
  参考文献：
  名称：

  Is there a role of taurine bromamine in inflammation? Interactive effects with nitrite and hydrogen peroxide

  摘要：

  Objective and Design: The myeloperoxidase system of neutrophils generates chlorinating and brominating oxidants in vivo. The major haloamines of the system are taurine chloramine (TauCl) and taurine bromamine (TauBr). It has been demonstrated in vitro that TauCl exerts both anti-inflammatory and anti-bacterial properties. Much less is known about TauBr. The present study was conducted to compare bactericidal and immunoregulatory capacity of TauBr with that of the major chlorinating oxidants: HOCl and TauCl. Moreover, the effect of nitrites and H2O2 on TauBr activity was investigated.Materials: TauBr was prepared by reaction of HOBr with taurine. The reaction was monitored by UV absorption spectra. Methods: Bactericidal activity of TauBr, TauCl and HOCl was tested by incubation of E. coli with the compounds and determined by the pour-plate method. To test the anti-inflammatory activity the compounds were incubated with LPS-and IFN-gamma stimulated murine peritoneal macrophages. The production of following mediators was measured: nitrites by Griess reaction; TNF-alpha, IL-6, IL-10, IL-12p40 using capture ELISA. In some experiments the compounds were incubated with either nitrites or H2O2.Results: In our experimental set-up TauBr and HOCl exerted strong bactericidal effects on E. coli (MBC = 110 muM and 8 muM, respectively), while TauCl (< 1000 muM) did not kill test bacteria. However, both, TauBr and TauCl, at non-cytotoxic concentrations (< 300 muM) inhibited the cytokine and nitric oxide production by macrophages. H2O2 completely abolished the biological activities of TauBr but not those of TauCl. Nitrites did not affect any activity of TauBr or TauCl while they diminished the HOCl- mediated bacterial killing.Conclusion: TauBr, despite very low concentration of Br- in body fluids, may support TauCl and HOCl in the regulation of inflammatory response and in killing of bacteria by neutrophils. However, TauBr activity in vivo will depend on the presence of H2O2 and possible other mediators of inflammation which can compete with target molecules for TauBr.

  DOI：

  10.1007/s00011-004-1322-9

文献信息

• Oxyhalogen–sulfur chemistry — Kinetics and mechanism of the bromate oxidation of cysteamine
  作者：Moshood K Morakinyo、Edward Chikwana、Reuben H Simoyi

  DOI：10.1139/v08-031

  日期：2008.5.1

  The kinetics and mechanism of the oxidation of the biologically important molecule, cysteamine, by acidic bromate and molecular bromine have been studied. In excess acidic bromate conditions, cysteamine is oxidized to N- brominated derivatives, and in excess cysteamine the oxidation product is taurine according to the following stoichiometry: BrO3 - +H 2NCH2CH2SH H2NCH2CH2SO3 H+B r - . There is quantitative

  研究了酸性溴酸盐和分子溴对生物学上重要的分子半胱胺进行氧化的动力学和机制。在过量的酸性溴酸盐条件下，半胱胺被氧化成N-溴化衍生物，并且在过量的半胱胺中，根据以下化学计量，氧化产物是牛磺酸：BrO3 - +H 2NCH2CH2SH H2NCH2CH2SO3 H+B r - 。在 N-溴化开始之前，牛磺酸会定量形成。过量的溴水溶液氧化半胱胺生成二溴牛磺酸： 5Br2 +H 2NCH2CH2 SH +3 H2O Br2NCH2CH2SO3H + 8Br - +8 H + ，而过量的半胱胺条件生成单溴牛磺酸。溴水溶液对半胱胺的氧化一直受到有效的扩散控制，直至形成单溴牛磺酸。二溴牛磺酸的进一步形成取决于酸浓度，在高酸性条件下抑制进一步反应形成二溴牛磺酸。牛磺酸的 N-溴化衍生物的形成是可逆的，牛磺酸在还原剂如碘化物的存在下再生。这一特性使牛磺酸能够在生理环境中减轻次溴酸的毒性。
• Simoyi, Reuben H.; Streete, Kevin; Mundoma, Claudius, South African Journal of Chemistry, 2002, vol. 55, p. 136 - 143
  作者：Simoyi, Reuben H.、Streete, Kevin、Mundoma, Claudius、Olojo, Rotimi

  DOI：——

  日期：——
• Is there a role of taurine bromamine in inflammation? Interactive effects with nitrite and hydrogen peroxide
  作者：J. Marcinkiewicz、M. Mak、M. Bobek、R. Biedroń、A. Białecka、M. Koprowski、E. Kontny、W. Maśliński

  DOI：10.1007/s00011-004-1322-9

  日期：2005.1

  Objective and Design: The myeloperoxidase system of neutrophils generates chlorinating and brominating oxidants in vivo. The major haloamines of the system are taurine chloramine (TauCl) and taurine bromamine (TauBr). It has been demonstrated in vitro that TauCl exerts both anti-inflammatory and anti-bacterial properties. Much less is known about TauBr. The present study was conducted to compare bactericidal and immunoregulatory capacity of TauBr with that of the major chlorinating oxidants: HOCl and TauCl. Moreover, the effect of nitrites and H2O2 on TauBr activity was investigated.Materials: TauBr was prepared by reaction of HOBr with taurine. The reaction was monitored by UV absorption spectra. Methods: Bactericidal activity of TauBr, TauCl and HOCl was tested by incubation of E. coli with the compounds and determined by the pour-plate method. To test the anti-inflammatory activity the compounds were incubated with LPS-and IFN-gamma stimulated murine peritoneal macrophages. The production of following mediators was measured: nitrites by Griess reaction; TNF-alpha, IL-6, IL-10, IL-12p40 using capture ELISA. In some experiments the compounds were incubated with either nitrites or H2O2.Results: In our experimental set-up TauBr and HOCl exerted strong bactericidal effects on E. coli (MBC = 110 muM and 8 muM, respectively), while TauCl (< 1000 muM) did not kill test bacteria. However, both, TauBr and TauCl, at non-cytotoxic concentrations (< 300 muM) inhibited the cytokine and nitric oxide production by macrophages. H2O2 completely abolished the biological activities of TauBr but not those of TauCl. Nitrites did not affect any activity of TauBr or TauCl while they diminished the HOCl- mediated bacterial killing.Conclusion: TauBr, despite very low concentration of Br- in body fluids, may support TauCl and HOCl in the regulation of inflammatory response and in killing of bacteria by neutrophils. However, TauBr activity in vivo will depend on the presence of H2O2 and possible other mediators of inflammation which can compete with target molecules for TauBr.