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ACS Chem Neurosci. 2018 Mar 21;9(3):563-567. doi: 10.1021/acschemneuro.7b00378. Epub 2017 Dec 8.

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

Author information

1
Research Triangle Institute , P.O. Box 12194, Research Triangle Park , North Carolina 27709 , United States.

Abstract

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 α R,5 R,9 R,13 S,14 S and α S,5 R,9 R,13 S,14 S 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.

KEYWORDS:

3-O-(α-carboxy-6-nitroveratryl)naloxone; diastereomers; photolabile

PMID:
29154536
DOI:
10.1021/acschemneuro.7b00378
[Indexed for MEDLINE]

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