N-nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine
• 英文别名: N-(3,4-dihydroxy-2-oxobutyl)-N-[2-(4-hydroxy-3-nitrophenyl)ethyl]nitrous amide
• 化学式: C₁₂H₁₅N₃O₇
• 分子量: 313.267
• InChiKey: ADFNSRMOWVEUNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-葡萄糖 、 L-酪氨酸 在 sodium nitrite 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 生成 N-nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine
  参考文献：
  名称：

  Promotional Effect of N-Nitroso-N-(3-keto-1,2-butanediol)-3′-nitrotyramine(a Nitrosated Maillard Reaction Product)in Mouse Fibroblast Cells

  摘要：

  N-Nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine (NO-NTA) is a product of model browning system generated in the presence of sodium nitrite. The chemical structure of this compound has been confirmed by UV, mass and nuclear magnetic resonance, and infrared spectroscopy in our previous study. A two-stage transformation protocol was used to chemically transform the mouse embryo fibroblasts C3H10T1/2 cells. To initiate transformation, the cells were treated with benzo[a]pyrene (BaP) (0.1 mg/ml), and NO-NTA (0.01, 0.1 and 1 mg/ml) was employed subsequently to complete the transformation process. Malignant transformed foci were formed in BaP-initiated and NO-NTA promoted C3H10T1/2 cells after 8 wk. Cells treated with NO-NTA alone failed to induce transformation. However, cells initiated with BaP and promoted by cells initiated with BaP and promoted by NO-NTA demonstrated oncogenic properties. Cell lines transformed with NO-NTA-transformed colonies exhibited enhanced growth rate, anchorage independence and tumorigenicity in animals relative to parent cells. These results indicate that NO-NTA is a new tumour promoter and may induce tumour promotion by two-stage oncogenesis. Further studies on the mechanism of action of NO-NTA are now in progress. (C) 1998 Elsevier Science Ltd. All rights reserved

  DOI：

  10.1016/s0278-6915(98)00033-7

文献信息

• N-Nitroso-N-(3-keto-1,2-butanediol)-3′-nitrotyramine
  作者：C. -J. Wang、H. -P. Huang、T. -H. Tseng、Y. -L. Lin、S. -J. Shiow

  DOI：10.1007/s002040050242

  日期：1995.11

  N-Nitroso-N-(3-keto-1,2-butanediol)-3'-nit rotyramine (NO-NTA) is a product of a model browning system in the presence of sodium nitrite. In this study, the chemical structure is confirmed by spectral studies, including UV, mass spectrometry, nuclear magnetic resonance and infrared spectroscopy. NO-NTA is strongly genotoxic to the rat hepatocyte and is moderately cytotoxic to mouse C3H10T1/2 cells. Results obtained in this study indicate that NO-NTA inflicted DNA damage through the formation of a DNA adduct. In addition, C3H10T1/2 cells were treated with NO-NTA and, following addition of 12-O-tetradecanoylphorbol-13-acetate (TPA) as promotor, the increase of transformed foci indicated that NO-NTA could possibly be an inhibitor of TPA tumor promotion. A transformed cell line from NO-NTA initiated and TPA promoted foci increased saturation density and growth ability in soft agar reactive to the control line. These results suggest that the formation of a genotoxic agent of nitroso-derivatives may take place in a nitrite-containing food system during processing and cooking.
• Promotional Effect of N-Nitroso-N-(3-keto-1,2-butanediol)-3′-nitrotyramine(a Nitrosated Maillard Reaction Product)in Mouse Fibroblast Cells
  作者：C.-J. Wang、H.-P. Huang、M.-J. Lee、Y.-L. Lin、W.-L. Lin、W.-C. Chang

  DOI：10.1016/s0278-6915(98)00033-7

  日期：1998.8

  N-Nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine (NO-NTA) is a product of model browning system generated in the presence of sodium nitrite. The chemical structure of this compound has been confirmed by UV, mass and nuclear magnetic resonance, and infrared spectroscopy in our previous study. A two-stage transformation protocol was used to chemically transform the mouse embryo fibroblasts C3H10T1/2 cells. To initiate transformation, the cells were treated with benzo[a]pyrene (BaP) (0.1 mg/ml), and NO-NTA (0.01, 0.1 and 1 mg/ml) was employed subsequently to complete the transformation process. Malignant transformed foci were formed in BaP-initiated and NO-NTA promoted C3H10T1/2 cells after 8 wk. Cells treated with NO-NTA alone failed to induce transformation. However, cells initiated with BaP and promoted by cells initiated with BaP and promoted by NO-NTA demonstrated oncogenic properties. Cell lines transformed with NO-NTA-transformed colonies exhibited enhanced growth rate, anchorage independence and tumorigenicity in animals relative to parent cells. These results indicate that NO-NTA is a new tumour promoter and may induce tumour promotion by two-stage oncogenesis. Further studies on the mechanism of action of NO-NTA are now in progress. (C) 1998 Elsevier Science Ltd. All rights reserved