Morphine-6beta-glucuronide and morphine-3-glucuronide, opioid receptor agonists with different potencies. 2001

C Ulens, and L Baker, and A Ratka, and D Waumans, and J Tytgat
University of Leuven, Faculty of Pharmaceutical Sciences, Laboratory of Toxicology, Van Evenstraat 4, 3000, Leuven, Belgium.

Using heterologous expression in Xenopus laevis oocytes, we compared the potencies of morphine, morphine-6beta-glucuronide (M6G), and morphine-3-glucuronide (M3G) for cloned human mu- (hMOR), kappa- (hKOR), and delta-opioid receptors (hDOR). Each receptor subtype was individually co-expressed with heteromultimeric G-protein coupled inwardly rectifying K(+) (GIRK) channels, consisting of GIRK1 and GIRK2 subunits, and RGS4, a regulator of G-protein signaling. The two-microelectrode voltage clamp technique was used to measure the opioid receptor-activated GIRK1/GIRK2 channel responses. Compared with morphine, M6G had higher potency at the hMOR, lower potency at the hKOR, and similar potency at the hDOR, while M3G showed a 1000-fold lower and non-selective potency via opioid receptors. In contrast to naloxone, M3G did not antagonize the effects of morphine at the hMOR. We also investigated whether Trp318 and His319 provide the molecular basis for mu/delta selectivity and mu/kappa selectivity of morphinan alkaloids by mutating these residues to their corresponding residues in kappa- and delta-opioid receptors. A single-point mutation (W318L) on hMOR completely conferred delta-like potency for morphine and M6G on the mutant mu-receptor. Double mutation at Trp318 and His319 positions (Trp318Y/His319Y) only partially conferred kappa-like potency for morphine and M6G; the decrease in potency for M6G was significantly larger than for morphine. The results of our study show that both M6G and M3G are opioid receptor agonists with different potencies and that the potency of morphinan receptor ligands can be changed by selective mutations of hMOR at the Trp318 and His319 positions.

UI MeSH Term Description Entries
D009020 Morphine The principal alkaloid in opium and the prototype opiate analgesic and narcotic. Morphine has widespread effects in the central nervous system and on smooth muscle. Morphine Sulfate,Duramorph,MS Contin,Morphia,Morphine Chloride,Morphine Sulfate (2:1), Anhydrous,Morphine Sulfate (2:1), Pentahydrate,Oramorph SR,SDZ 202-250,SDZ202-250,Chloride, Morphine,Contin, MS,SDZ 202 250,SDZ 202250,SDZ202 250,SDZ202250,Sulfate, Morphine
D009022 Morphine Derivatives Analogs or derivatives of morphine. Morphines
D009865 Oocytes Female germ cells derived from OOGONIA and termed OOCYTES when they enter MEIOSIS. The primary oocytes begin meiosis but are arrested at the diplotene state until OVULATION at PUBERTY to give rise to haploid secondary oocytes or ova (OVUM). Ovocytes,Oocyte,Ovocyte
D011957 Receptors, Opioid Cell membrane proteins that bind opioids and trigger intracellular changes which influence the behavior of cells. The endogenous ligands for opioid receptors in mammals include three families of peptides, the enkephalins, endorphins, and dynorphins. The receptor classes include mu, delta, and kappa receptors. Sigma receptors bind several psychoactive substances, including certain opioids, but their endogenous ligands are not known. Endorphin Receptors,Enkephalin Receptors,Narcotic Receptors,Opioid Receptors,Receptors, Endorphin,Receptors, Enkephalin,Receptors, Narcotic,Receptors, Opiate,Endorphin Receptor,Enkephalin Receptor,Normorphine Receptors,Opiate Receptor,Opiate Receptors,Opioid Receptor,Receptors, Normorphine,Receptors, beta-Endorphin,beta-Endorphin Receptor,Receptor, Endorphin,Receptor, Enkephalin,Receptor, Opiate,Receptor, Opioid,Receptor, beta-Endorphin,Receptors, beta Endorphin,beta Endorphin Receptor,beta-Endorphin Receptors
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000701 Analgesics, Opioid Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. Opioid,Opioid Analgesic,Opioid Analgesics,Opioids,Full Opioid Agonists,Opioid Full Agonists,Opioid Mixed Agonist-Antagonists,Opioid Partial Agonists,Partial Opioid Agonists,Agonist-Antagonists, Opioid Mixed,Agonists, Full Opioid,Agonists, Opioid Full,Agonists, Opioid Partial,Agonists, Partial Opioid,Analgesic, Opioid,Full Agonists, Opioid,Mixed Agonist-Antagonists, Opioid,Opioid Agonists, Full,Opioid Agonists, Partial,Opioid Mixed Agonist Antagonists,Partial Agonists, Opioid
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D014982 Xenopus laevis The commonest and widest ranging species of the clawed "frog" (Xenopus) in Africa. This species is used extensively in research. There is now a significant population in California derived from escaped laboratory animals. Platanna,X. laevis,Platannas,X. laevi
D017450 Receptors, Opioid, mu A class of opioid receptors recognized by its pharmacological profile. Mu opioid receptors bind, in decreasing order of affinity, endorphins, dynorphins, met-enkephalin, and leu-enkephalin. They have also been shown to be molecular receptors for morphine. Morphine Receptors,Opioid Receptors, mu,Receptors, Morphine,Receptors, mu,Receptors, mu Opioid,mu Receptors,Morphine Receptor,mu Opioid Receptor,mu Receptor,Opioid Receptor, mu,Receptor, Morphine,Receptor, mu,Receptor, mu Opioid,mu Opioid Receptors
D017465 Receptors, Opioid, delta A class of opioid receptors recognized by its pharmacological profile. Delta opioid receptors bind endorphins and enkephalins with approximately equal affinity and have less affinity for dynorphins. Opioid Receptors, delta,Receptors, delta,Receptors, delta Opioid,delta Receptors,delta Opioid Receptor,delta Receptor,Opioid Receptor, delta,Receptor, delta,Receptor, delta Opioid,delta Opioid Receptors

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