TY - JOUR
T1 - Synthesis, conformation, and biological characterization of a sugar derivative of morphine that is a potent, long-lasting, and nontolerant antinociceptive
AU - Arsequell, Gemma
AU - Salvatella, Mariona
AU - Valencia, Gregorio
AU - Fernández-Mayoralas, Alfonso
AU - Fontanella, Marco
AU - Venturi, Chiara
AU - Jiménez-Barbero, Jesús
AU - Marrón, Ezequiel
AU - Rodríguez, Raquel E.
PY - 2009/5/14
Y1 - 2009/5/14
N2 - 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.
AB - 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.
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U2 - 10.1021/jm8011245
DO - 10.1021/jm8011245
M3 - Article
C2 - 19351163
AN - SCOPUS:65649100070
SN - 0022-2623
VL - 52
SP - 2656
EP - 2666
JO - Journal of medicinal chemistry
JF - Journal of medicinal chemistry
IS - 9
ER -