Gulaboski, Rubin and Cordeiro, M Natália D S and Milhazes, Nuno and Garrido, Jorge and Borges, Fernanda and Jorge, Miguel and Pereira, Carlos M. and Bogeski, Ivan and Morales, Aluska Helguera and Naumoski, Blaze and Silva, A. Fernando (2007) Evaluation of the lipophilic properties of opioids, amphetamine-like drugs, and metabolites through electrochemical studies at the interface between two immiscible solutions. Analytical Biochemistry, 361 (2). pp. 236-243. ISSN 00032697
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Abstract
For the first time, the partition coefficients of the ionized forms of several opioids, amphetamine-like drugs, and their metabolites were
determined by studying their ionic transfer process across the bare interface waterjorganic solvent. The ionic partition coefficients of the
monocationic forms of 12 compounds—heroin, 6-monoacetylmorphine (6-MAM), morphine, acetylcodeine, codeine, dihydrocodeine,
methamphetamine, amphetamine, 3,4-methylenedioxymethamphetamine (MDMA or ‘‘ecstasy’’), 3,4-methylenedioxyamphetamine
(MDA), 3-methoxy-a-methyldopamine (3-OMe-a-MeDA), and a-methyldopamine (a-MeDA)—were attained using electrochemical
measurements, by cyclic voltammetry, at the interface between two immiscible electrolyte solutions (ITIES). Then the acquired lipophilicity
values were correlated to the chemical structure of the compounds and with the metabolic pathways central to each class of drugs.
Although the mechanisms of biotoxicity of this type of drugs are still unclear, the data obtained evidence that the lipophilicity of metabolites
may be a contributing factor for the qualitative differences found in their activity. In addition, the partition coefficients of the ionic
drugs were calculated using three available software packages: ModesLab, Dragon, and HyperChem. As shown by cross-comparison of
the experimental and calculated values, HyperChem was the most reliable software for achieving the main goal. The data obtained so far
seem to be correlated to the proposed metabolic pathways of the drugs and could be of great value in understanding their pharmacological
and/or toxicological profiles at the molecular level. This study may also contribute to gaining an insight into the mechanisms of
biotransportation of this type of compounds given that the ionic partition coefficients reflect their ability to cross the membrane barriers.
� 2006 Elsevier Inc. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | drugs, ion transfer, liquid-liquid interface, partition |
| Subjects: | Natural sciences > Chemical sciences |
| Divisions: | Faculty of Agriculture |
| Depositing User: | Rubin Gulaboski |
| Date Deposited: | 30 Oct 2012 17:20 |
| Last Modified: | 05 Nov 2012 10:47 |
| URI: | https://eprints.ugd.edu.mk/id/eprint/98 |
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