PENAA | 1022085-60-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: PENAA
• 英文别名: 4-(N-(S-penicillaminylacetyl)amino) phenylarsenic acid；(S)-penicillamine-arsonic acid
• CAS: 1022085-60-4
• 化学式: C₁₃H₁₉AsN₂O₆S
• 分子量: 406.291
• InChiKey: CDKXUNISYAYIHV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.89
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  149.95
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对氨基苯砷酸 在 碳酸氢钠 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 6.62h， 生成 PENAA
  参考文献：
  名称：

  WO2008/52279

  摘要：

  公开号：

文献信息

• Optimization of the Antitumor Efficacy of a Synthetic Mitochondrial Toxin by Increasing the Residence Time in the Cytosol
  作者：Pierre J. Dilda、Stéphanie Decollogne、Lakmini Weerakoon、Murray D. Norris、Michelle Haber、John D. Allen、Philip J. Hogg

  DOI：10.1021/jm9008339

  日期：2009.10.22

  Plasma membrane drug efflux pumps of the multidrug resistance associated protein (MRP) family blunt the effectiveness of anticancer drugs and are often associated with drug resistance. GSAO, a tripeptide trivalent arsenical that targets a key mitochondrial transporter in angiogenic endothelial cells, is an example of a compound whose efficacy is limited by tumor cell expression of MRP isoforms 1 and 2. A cysteine mimetic analogue of GSAO was made, PENAO, which accumulates in cells 85 times faster than GSAO due to increased rate of entry and decreased rate of export via MRP1/2. The faster rate of accumulation of PENAO corresponds to a 44-fold increase in antiproliferative activity in vitro and similar to 20-fold better antitumor efficacy in vivo. This information could be used to improve the efficacy of other small molecule cancer therapeutics.