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Monoterpenes affect chlorodiazepoxide-micelle interaction through micellar dipole potential modifications
Anahí V Turina1, Anahí V del Turina, María A Perillo
1Cátedra de Biofísica Química, Depto. de Química, Facultad de Ciencias Exactas, Físicas y Naturales, Universidad Nacional de Córdoba, Av. Velez Sarsfield 1611, X5016CAG Córdoba, Argentina.
Biochimica Et Biophysica Acta
|October 17, 2003
Summary
Natural terpenes alter membrane environments by influencing benzodiazepine interactions. These compounds modify micelle dipole potentials, affecting drug partitioning and membrane phase behavior.
Area of Science:
- Biophysical Chemistry
- Membrane Biophysics
- Pharmacology
Background:
- Benzodiazepines (BZD) are a class of psychoactive drugs.
- Understanding drug-membrane interactions is crucial for pharmacology.
- Natural terpenes are known for diverse biological activities.
Purpose of the Study:
- To investigate how natural terpenes affect benzodiazepine-micelle interactions.
- To explore the influence of terpenes on membrane dipolar organization.
- To determine the impact of terpenes on the partitioning of chlorodiazepoxide (CDX).
Main Methods:
- Utilized Triton X-100 micelles to mimic a cellular membrane environment.
- Investigated the acid-base equilibrium of chlorodiazepoxide (CDX).
- Measured the spectroscopic behavior of the electrochromic dye merocyanine.
- Assayed the effects of cineole, menthol, geraniol, and camphor.
Main Results:
- Terpenes increased the apparent pK of CDX in micelle environments.
- Calculated decrements in electric potentials ranged from -111 to -128 mV.
- The dielectric constant sensed by merocyanine increased from D=9 to D≈11 in the presence of terpenes.
- Merocyanine partitioning decreased, indicating increased negative dipole potential.
Conclusions:
- Natural terpenes significantly alter the dipolar organization of micelle interfaces.
- Terpenes create a more negative environment at the membrane interface, enhancing CDX membrane phase preference.
- The findings suggest terpenes can modulate drug-membrane interactions through dipole moment contributions.