hydropropidine | 1418010-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: hydropropidine
• 英文别名: 3-(3,8-diamino-6-phenyl-6H-phenanthridin-5-yl)propyl-diethyl-methylazanium
• CAS: 1418010-07-7
• 化学式: C₂₇H₃₅N₄
• 分子量: 415.602
• InChiKey: DGVZJSDAVOKFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  hydropropidine 在 potassium hexacyanoferrate(III) 作用下， 生成 dipropidium
  参考文献：
  名称：

  Hydropropidine: A novel, cell-impermeant fluorogenic probe for detecting extracellular superoxide

  摘要：

  Here we report the synthesis and characterization of a membrane-impermeant fluorogenic probe, hydropropidine (HPr+), the reduction product of propidium iodide, for detecting extracellular superoxide (O-2(center dot-)). HPr+ is a positively charged water-soluble analog of hydroethidine (HE), a fluorogenic probe commonly used for monitoring intracellular O-2(center dot-). We hypothesized that the presence of a highly localized positive charge on the nitrogen atom would impede cellular uptake of HPr+ and allow for exclusive detection of extracellular O-2(center dot-). Our results indicate that O-2(center dot-) reacts with HPr+ (k=1.2 x 10(4) M-1 s(-1)) to form exclusively 2-hydroxypropidium (2-OH-Pr2+) in cell-free and cell-based systems. This reaction is analogous to the reaction between HE and O-2(center dot-) (Zhao et al., Free Radic. Biol. Med. 34:1359-1368; 2003). During the course of this investigation, we also reassessed the rate constants for the reactions of O-2(center dot-) with HE and its mitochondria targeted analog (Mito-HE or MitoSOX Red) and addressed the discrepancies between the present values and those reported previously by us. Our results indicate that the rate constant between O-2(center dot-) and HPr+ is slightly higher than that of HE and O-2(center dot-) and is closer to that of Mito-HE and O-2(center dot-). Similar to HE, HPr+ undergoes oxidation in the presence of various oxidants (peroxynitrite-derived radicals, Fenton's reagent, and ferricytochrome c) forming the corresponding propidium dication (Pr2+) and the dimeric products (e.g., Pr2+-Pr2+). In contrast to HE, there was very little intracellular uptake of HPr+. We conclude that HPr+ is a useful probe for detecting O-2(center dot-) and other one-electron oxidizing species in an extracellular milieu. (C) 2012 Published by Elsevier Inc.

  DOI：

  10.1016/j.freeradbiomed.2012.09.018
• 作为产物：
  描述：

  propidium iodide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 hydropropidine
  参考文献：
  名称：

  Hydropropidine: A novel, cell-impermeant fluorogenic probe for detecting extracellular superoxide

  摘要：

  Here we report the synthesis and characterization of a membrane-impermeant fluorogenic probe, hydropropidine (HPr+), the reduction product of propidium iodide, for detecting extracellular superoxide (O-2(center dot-)). HPr+ is a positively charged water-soluble analog of hydroethidine (HE), a fluorogenic probe commonly used for monitoring intracellular O-2(center dot-). We hypothesized that the presence of a highly localized positive charge on the nitrogen atom would impede cellular uptake of HPr+ and allow for exclusive detection of extracellular O-2(center dot-). Our results indicate that O-2(center dot-) reacts with HPr+ (k=1.2 x 10(4) M-1 s(-1)) to form exclusively 2-hydroxypropidium (2-OH-Pr2+) in cell-free and cell-based systems. This reaction is analogous to the reaction between HE and O-2(center dot-) (Zhao et al., Free Radic. Biol. Med. 34:1359-1368; 2003). During the course of this investigation, we also reassessed the rate constants for the reactions of O-2(center dot-) with HE and its mitochondria targeted analog (Mito-HE or MitoSOX Red) and addressed the discrepancies between the present values and those reported previously by us. Our results indicate that the rate constant between O-2(center dot-) and HPr+ is slightly higher than that of HE and O-2(center dot-) and is closer to that of Mito-HE and O-2(center dot-). Similar to HE, HPr+ undergoes oxidation in the presence of various oxidants (peroxynitrite-derived radicals, Fenton's reagent, and ferricytochrome c) forming the corresponding propidium dication (Pr2+) and the dimeric products (e.g., Pr2+-Pr2+). In contrast to HE, there was very little intracellular uptake of HPr+. We conclude that HPr+ is a useful probe for detecting O-2(center dot-) and other one-electron oxidizing species in an extracellular milieu. (C) 2012 Published by Elsevier Inc.

  DOI：

  10.1016/j.freeradbiomed.2012.09.018

文献信息

• Hydropropidine: A novel, cell-impermeant fluorogenic probe for detecting extracellular superoxide
  作者：Radoslaw Michalski、Jacek Zielonka、Micael Hardy、Joy Joseph、Balaraman Kalyanaraman

  DOI：10.1016/j.freeradbiomed.2012.09.018

  日期：2013.1

  Here we report the synthesis and characterization of a membrane-impermeant fluorogenic probe, hydropropidine (HPr+), the reduction product of propidium iodide, for detecting extracellular superoxide (O-2(center dot-)). HPr+ is a positively charged water-soluble analog of hydroethidine (HE), a fluorogenic probe commonly used for monitoring intracellular O-2(center dot-). We hypothesized that the presence of a highly localized positive charge on the nitrogen atom would impede cellular uptake of HPr+ and allow for exclusive detection of extracellular O-2(center dot-). Our results indicate that O-2(center dot-) reacts with HPr+ (k=1.2 x 10(4) M-1 s(-1)) to form exclusively 2-hydroxypropidium (2-OH-Pr2+) in cell-free and cell-based systems. This reaction is analogous to the reaction between HE and O-2(center dot-) (Zhao et al., Free Radic. Biol. Med. 34:1359-1368; 2003). During the course of this investigation, we also reassessed the rate constants for the reactions of O-2(center dot-) with HE and its mitochondria targeted analog (Mito-HE or MitoSOX Red) and addressed the discrepancies between the present values and those reported previously by us. Our results indicate that the rate constant between O-2(center dot-) and HPr+ is slightly higher than that of HE and O-2(center dot-) and is closer to that of Mito-HE and O-2(center dot-). Similar to HE, HPr+ undergoes oxidation in the presence of various oxidants (peroxynitrite-derived radicals, Fenton's reagent, and ferricytochrome c) forming the corresponding propidium dication (Pr2+) and the dimeric products (e.g., Pr2+-Pr2+). In contrast to HE, there was very little intracellular uptake of HPr+. We conclude that HPr+ is a useful probe for detecting O-2(center dot-) and other one-electron oxidizing species in an extracellular milieu. (C) 2012 Published by Elsevier Inc.