dihydronicotinamide adenine dinucleotide | 58001-40-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: dihydronicotinamide adenine dinucleotide
• 英文别名: nicotinamide-adenin-dinucleotide reduced；NADH；O^5'-{2-[1-(3-carbamoyl-4H-pyridin-1-yl)-D-1-deoxy-ribofuranos-5-yloxy]-1,2-dihydroxy-phosphoryl}-adenosine；[[(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 58001-40-4
• 化学式: C₂₁H₂₉N₇O₁₄P₂
• 分子量: 665.447
• InChiKey: BOPGDPNILDQYTO-JTDWVUTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  318
• 氢给体数：
  8
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  dihydronicotinamide adenine dinucleotide 在 hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  直接观察与单电子氧化剂反应产生的 NADH 自由基阳离子

  摘要：

  首次观察到在与单电子氧化剂反应中形成NADH自由基阳离子。涉及两种互变异构体（酮和烯醇）形式的自由基阳离子和中性自由基的瞬态产物通过脉冲辐射分解的光谱特征进行了表征。研究了酮基阳离子和中性自由基的衰变动力学。测定了烯醇形式的NADH自由基阳离子的pKa值。研究了 NADH 和 NAD+ 的简单类似物，即 1-甲基-1,4-二氢烟酰胺及其氧化形式，以进行比较。

  DOI：

  10.1021/jp035803y
• 作为产物：
  描述：

  nicotinamide-adenin-dinucleotide oxidized 在 sodium dithionite 作用下， 以 sodium hydroxide 、 水 为溶剂， 生成 dihydronicotinamide adenine dinucleotide
  参考文献：
  名称：

  Sulfoxylate ion (HSO2-), the hydride donor in dithionite-dependent reduction of NAD+ analogs

  摘要：

  DOI：

  10.1021/ja00523a028
• 作为试剂：
  描述：

  磺胺甲恶唑羟胺 在 dihydronicotinamide adenine dinucleotide 、 recombinant human mitochondrial amidoxime reducing component-2 wild type protein 作用下， 以 aq. buffer 为溶剂， 反应 0.33h， 生成 磺胺甲恶唑
  参考文献：
  名称：

  Reduction of Sulfamethoxazole Hydroxylamine (SMX-HA) by the Mitochondrial Amidoxime Reducing Component (mARC)

  摘要：

  Under high dose treatment with sulfamethoxazole (SMX)/trimethoprim (TMP), hypersensitivity reactions occur with a high incidence. The mechanism of this adverse drug reaction is not fully understood. Several steps in the toxification pathway of SMX were investigated. The aim of our study was to investigate the reduction of sulfamethoxazole hydroxylamine (SMX-HA) in this toxification pathway, which can possibly be catalyzed by the mARC-containing N-reductive enzyme system. Western blot analyses of subcellular fractions of porcine tissue were performed with antibodies against mARC-1, mARC-2, cytochrome b(5) type B, and NADH cytochrome b(5) reductase. Incubations of porcine and human subcellular tissue fractions and of the heterologously expressed human components of the N-reductive enzyme system were carried out with SMX-HA. mARC-1 and rnARC-2 knockdown was performed in HEK-293 cells. Kinetic parameters of the heterologously expressed human protein variants V96L, A165T, M187K, C246S, D247H, and M268I of mARC-1 and G244S and C245W of mARC-2 and N-reductive activity of 2SF, D14G, K16E, and T22A of cytochrome b(5) type B were analyzed. Western blot analyses were consistent with the hypothesis that the mARC-containing N-reductive enzyme system might be involved in the reduction of SMX-HA. In agreement with these results, highest reduction rates were found in mitochondrial subcellular fractions of porcine tissue and in the outer membrane vesicle (OMV) of human liver tissue. Knockdown studies in HEK-293 cells demonstrated that mARC-1 and mARC-2 were capable of reducing SMX-HA in cell metabolism. Investigations with the heterologously expressed human mARC-2 protein showed a higher catalytic efficiency toward SMX-HA than mARC-1, but none of the investigated human protein variants showed statistically significant differences of its N-reductive activity and was therefore likely to participate in the pathogenesis of hypersensitivity reaction under treatment with SMX.

  DOI：

  10.1021/tx500174u