4-[(1-hydroxypropan-2-ylamino)methyl]-5-(hydroxymethyl)-2-methylpyridin-3-ol | 1042935-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[(1-hydroxypropan-2-ylamino)methyl]-5-(hydroxymethyl)-2-methylpyridin-3-ol
• 英文别名: 5-(Hydroxymethyl)-4-[(1-hydroxypropan-2-ylamino)methyl]-2-methylpyridin-3-ol；5-(hydroxymethyl)-4-[(1-hydroxypropan-2-ylamino)methyl]-2-methylpyridin-3-ol
• CAS: 1042935-72-7
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: NADNYZJSBQCZGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.6
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟基丙酮 、 吡多胺 在 sodium cyanoborohydride 作用下， 以 phosphate buffer 为溶剂， 反应 10.0h， 生成 4-[(1-hydroxypropan-2-ylamino)methyl]-5-(hydroxymethyl)-2-methylpyridin-3-ol
  参考文献：
  名称：

  The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect

  摘要：

  Amadori compounds act as precursors in the formation of advanced glycation end products (AGEs) by non-enzymatic protein glycation, which are involved in ensuing protein damage. Pyridoxamine is a potent drug against protein glycation, and can act on several pathways in the glycation process. Nevertheless, the pyridoxamine inhibition action on Amadori compounds oxidation is still unclear. In this work, we have studied the Schiff base formation between pyridoxamine and various Amadori models at pH 7.4 at 37 degrees C in the presence of NaCNBH(3). We detected an adduct formation, which suggests that pyridoxamine reacts with the carbonyl group in Amadori compounds. The significance of this mechanism is tested by comparison of the obtained kinetics rate constants with that obtained for 4-(aminomethyl)-pyridine, a structural analogue of pyridoxamine without post-Amadori action. We also study the chelating effect of pyridoxamine on metal ions. We have determined the complexation equilibrium constants between pyridoxamine, N-(1-deoxy-D-fructos-1-yl)-L-tryptophan, aminoguanidine, and ascorbic acid in the presence of Zn(2+). The results show that the strong stability of pyridoxamine complexes is the key in its post-Amadori inhibition action. On the other hand results explain the lack of inhibition of aminoguanidine ( a glycation inhibitor) in the post-Amadori reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.002

文献信息

• The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect
  作者：Miquel Adrover、Bartolomé Vilanova、Juan Frau、Francisco Muñoz、Josefa Donoso

  DOI：10.1016/j.bmc.2008.04.002

  日期：2008.5

  Amadori compounds act as precursors in the formation of advanced glycation end products (AGEs) by non-enzymatic protein glycation, which are involved in ensuing protein damage. Pyridoxamine is a potent drug against protein glycation, and can act on several pathways in the glycation process. Nevertheless, the pyridoxamine inhibition action on Amadori compounds oxidation is still unclear. In this work, we have studied the Schiff base formation between pyridoxamine and various Amadori models at pH 7.4 at 37 degrees C in the presence of NaCNBH(3). We detected an adduct formation, which suggests that pyridoxamine reacts with the carbonyl group in Amadori compounds. The significance of this mechanism is tested by comparison of the obtained kinetics rate constants with that obtained for 4-(aminomethyl)-pyridine, a structural analogue of pyridoxamine without post-Amadori action. We also study the chelating effect of pyridoxamine on metal ions. We have determined the complexation equilibrium constants between pyridoxamine, N-(1-deoxy-D-fructos-1-yl)-L-tryptophan, aminoguanidine, and ascorbic acid in the presence of Zn(2+). The results show that the strong stability of pyridoxamine complexes is the key in its post-Amadori inhibition action. On the other hand results explain the lack of inhibition of aminoguanidine ( a glycation inhibitor) in the post-Amadori reactions. (C) 2008 Elsevier Ltd. All rights reserved.