Electronic study of receptor binding of analgesic aryl moiety II: Prodine analogs

Razzak, Khalid Sabih A.; Hamid, Khawla A.

doi:10.1002/jps.2600690713

Cited by 4 publications

(3 citation statements)

References 13 publications

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“…The influence of the TF properties on OR ligand affinity has been extensively studied and it has been established that the protonated nitrogen atom in the TF (below, TF nitrogen) accounts for its ionic interaction with an anion group of the complementary OR site, supported by the hydrogen bond (H-bond) formation [9 -12]. The aryl fragment forms a charge-transfer complex (CTC) with a certain complementary site of the OR [5,13]. A substituent in the phenyl ring acts as a proton donor and forms an H-bond with the OR [6,14,15].…”

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Effect of the tyramine fragment of opioid receptor ligands on their agonist and antagonist properties

et al. 2006

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A comparative analysis of correlations between the ED 50 and AD 50 values describing the agonist and antagonist properties of opioid receptor ligands, on the one hand, and molecular descriptors related to the electronic and geometric properties of the tyramine moiety of these ligands, on the other hand, has been carried out. The affinity of ligands to the complementary site of opioid receptors depends on the electronic properties of the tyramine moiety, such as the basicity of the TF nitrogen atom, the electron-acceptor properties of the "cation head," the electron-donor properties of the aryl moiety, and the ability of substituent atoms in the aryl moiety to act as proton donors and form hydrogen bonds with the OR. The intrinsic activity of ligands depends on the coplanarity of atoms of the substituent in the aryl moiety to the phenyl ring plane. Substantial protrusion of substituent atoms out of the plane of the phenyl ring apparently prevents penetration of a ligand deep into "binding pocket" of the receptor, which leads to disappearance of the antagonist properties of this ligand. 254 0091-150X/06/4005-0254

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Effect of the tyramine fragment of opioid receptor ligands on their agonist and antagonist properties

et al. 2006

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“…A positively charged nitrogen atom in the TF accounts for the electrostatic interaction with the anion group of an opioid receptor, which is supplemented by hydrogen bonding [7,8]. The aryl moiety of the TF forms a charge transfer complex with a certain complementary region of the opioid receptor [9].…”

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“…In the literature devoted to quantum-chemical calculations of the structure of model compounds, the electron properties of the aryl moiety of the TF were described on the basis of estimated charge density distributions in protonated molecules of morphine-like analgesics [10] and on the basis of a comparative analysis of the opiate activity of prodine analogs and the energies of frontal boundary molecular orbitals of their aryl moieties [9]. The results of these investigations led to a conclusion that the aryl moiety, which forms a charge transfer complex with a certain complementary region of the opioid receptor, plays the role of an electron donor.…”

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Electron properties of aryl moieties in agonists and antagonists of opioid receptors

et al. 2005

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The electron properties of aryl moieties in the molecules of opioid receptor agonists and antagonists are compared in terms of the normalized atomic contributions of electron density to the frontal boundary molecular orbitals. Ligands in the neutral and protonated forms, as well as in the "ligand -receptor fragment" complexes (associates), are considered. The electron properties of the aryl moiety depend on the order in which the active centers of its tyramine fragment interact with the complementary region of an opioid receptor. It is suggested that the electron properties of aryl moieties determine the affinity of molecules to opioid receptors but do not influence the level of internal activity of such ligands.

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Pethidine and Related 4-Phenylpiperidine Analgesics

Casy

Parfitt

1986

Opioid Analgesics

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Electronic study of receptor binding of analgesic aryl moiety II: Prodine analogs

Cited by 4 publications

References 13 publications

Effect of the tyramine fragment of opioid receptor ligands on their agonist and antagonist properties

Effect of the tyramine fragment of opioid receptor ligands on their agonist and antagonist properties

Electron properties of aryl moieties in agonists and antagonists of opioid receptors

Pethidine and Related 4-Phenylpiperidine Analgesics

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