Caged Naloxone: Synthesis, Characterization, and Stability of 3-O-(4,5-Dimethoxy-2-nitrophenyl)carboxymethyl Naloxone (CNV-NLX),ACS Chemical Neuroscience

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Caged Naloxone: Synthesis, Characterization, and Stability of 3-O-(4,5-Dimethoxy-2-nitrophenyl)carboxymethyl Naloxone (CNV-NLX)
ACS Chemical Neuroscience ( IF 4.1 ) Pub Date : 2017-11-20 00:00:00 , DOI: 10.1021/acschemneuro.7b00378
Anita H. Lewin ₁ , Scott E. Fix ₁ , Desong Zhong ₁ , Louise D. Mayer ₁ , Jason P. Burgess ₁ , S. Wayne Mascarella ₁ , P. Anantha Reddy ₁ , Herbert H. Seltzman ₁ , F. Ivy Carroll ₁

Affiliation

The photolabile analogue of the broad-spectrum opioid antagonist naloxone, 3-O-(4,5-dimethoxy-2-nitrophenyl)carboxymethyl naloxone (also referred to as “caged naloxone”, 3-O-(α-carboxy-6-nitroveratryl)naloxone, CNV-NLX), has been found to be a valuable biochemical probe. While the synthesis of CNV-NLX is simple, its characterization is complicated by the fact that it is produced as a mixture of αR,5R,9R,13S,14S and αS,5R,9R,13S,14S diastereomers. Using long-range and heteronuclear NMR correlations, the ¹H NMR and ¹³C NMR resonances of both diastereomers have been fully assigned, confirming the structures. Monitoring of solutions of CNV-NLX in saline buffer, in methanol, and in DMSO has shown CNV-NLX to be stable for over a week under fluorescent laboratory lights at room temperature. Exposure of such solutions to λ 365 nm from a hand-held UV lamp led to the formation of naloxone and CNV-related breakdown products.

中文翻译：

笼养纳洛酮：3 - O-（4,5-二甲氧基-2-硝基苯基）羧甲基纳洛酮（CNV-NLX）的合成，表征和稳定性

广谱阿片样物质拮抗剂纳洛酮的光不稳定类似物3- O-（4,5-二甲氧基-2-硝基苯基）羧甲基纳洛酮（也称为笼养纳洛酮），3- O-（α-羧基-6-已经发现，硝化萘二酮，纳洛酮（CNV-NLX）是一种有价值的生化探针。虽然CNV-NLX的合成简便，其特征是由它产生作为α的混合物的事实而复杂化- [R，5 - [R，9 - [R，13小号，14小号和α小号，5 - [R，9 - [R，13 S，14S个非对映异构体。使用远程和异核NMR相关性，¹两种非对映异构体的1 H NMR和¹³ C NMR共振已完全确定，从而确认了结构。监测CNV-NLX在盐水缓冲液，甲醇和DMSO中的溶液，显示CNV-NLX在室温下的荧光实验室灯下可稳定一周以上。此类溶液从手持式紫外线灯照射到365 nm处会导致形成纳洛酮和与CNV相关的分解产物。

更新日期：2017-11-20

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