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2009:
Arsequell Gemma; Salvatella Mariona; Valencia Gregorio; Fernández-Mayoralas Alfonso; Fontanella Marco; Venturi Chiara; Jiménez-Barbero Jesús; Marrón Ezequiel; Rodríguez Raquel E
Synthesis, conformation, and biological characterization of a sugar derivative of morphine that is a potent, long-lasting, and nontolerant antinociceptive.
Journal of medicinal chemistry 2009;
52(
9):.
A synthetic mannoside derivative, namely, 6-morphinyl-alpha-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 mu 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.
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