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

AuthorsArsequell, Gemma ; Salvatella, Mariona; Valencia, Gregorio; Fernández-Mayoralas, Alfonso ; Fontanella, Marco ; Venturi, Chiara; Jiménez-Barbero, Jesús ; Marrón Fernández de Velasco, E.; Rodríguez, Raquel E.
Issue Date7-Apr-2009
PublisherAmerican Chemical Society
CitationJournal of Medicinal Chemistry 52(9): 2656-2666 (2009)
AbstractA synthetic mannoside derivative, namely, 6-morphinyl-α-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.
Description11 pages.-- PMID: 19351163 [PubMed].-- Printed version published May 14, 2009.
Supporting information (10 pages) available at: http://pubs.acs.org/doi/suppl/10.1021/jm8011245/suppl_file/jm8011245_si_001.pdf
Publisher version (URL)http://dx.doi.org/10.1021/jm8011245
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