一种吗啡糖衍生物的合成、构象及生物学特性，该衍生物是一种强效、长效且无耐受性的抗伤害感受剂。

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

作者信息

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

机构信息

Unit of Glycoconjugate Chemistry, Instituto de Química Avanzada de Cataluña (IQAC-CSIC), Barcelona, Jordi Girona 18-26, E08034-Barcelona, Spain.

出版信息

J Med Chem. 2009 May 14;52(9):2656-66. doi: 10.1021/jm8011245.

DOI:10.1021/jm8011245

PMID:19351163

Abstract

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.

摘要

一种合成甘露糖苷衍生物，即6-吗啡基-α-D-甘露吡喃糖苷，在大鼠的爪部压力和甩尾试验中腹腔注射时，显示出纳洛酮可逆的抗伤害感受作用，其效力比吗啡强100倍，持续时间是吗啡的两倍。该化合物不会产生耐受性，并且与大鼠μ阿片受体的结合亲和力是吗啡的两倍。核磁共振研究表明，该衍生物与其母体化合物M6G之间活性的差异可能与其不同的分子动力学行为有关。