Synthesis, conformation, and biological characterization of a sugar derivative of morphine that is a potent, long-lasting, and nontolerant antinociceptive

Gemma Arsequell, Mariona Salvatella, Gregorio Valencia, Alfonso Fernández-Mayoralas, Marco Fontanella, Chiara Venturi, Jesús Jiménez-Barbero, Ezequiel Marrón, Raquel E. Rodríguez

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

A synthetic mannoside derivative, namely, 6-morphinyl-R-D-mannopyranoside, shows a naloxone-reversible antinociception that is 100-fold more potent and twice as long lasting compared to morphine when administered intraperitoneally to rats in paw pressure and tail flick tests. The compound does not produce tolerance and binds to rat μ opioid receptors with twice the affinity of morphine. NMR studies suggest that differences of activity between the derivative and its parent compound M6G might be related to their differing molecular dynamic behavior.

Original languageEnglish (US)
Pages (from-to)2656-2666
Number of pages11
JournalJournal of medicinal chemistry
Volume52
Issue number9
DOIs
StatePublished - May 14 2009
Externally publishedYes

Fingerprint

Dive into the research topics of 'Synthesis, conformation, and biological characterization of a sugar derivative of morphine that is a potent, long-lasting, and nontolerant antinociceptive'. Together they form a unique fingerprint.

Cite this