Thermodynamics of Partitioning of the Antimalarial Drug Mefloquine in Phospholipid Bilayers and Bulk Solvents

スポンサーリンク

概要

• 論文の詳細を見る

• The antimalarial drug mefloquine binds avidly to phospholipids in biomembranes. The thermodynamics of the partitioning process in dimyristoylphosphatidylcholine (DMPC) bilayers was investigated to give insight into the drug-phospholipid interaction. Thermodynamic parameters for the partition equilibria were evaluated from the equilibrium partition coefficients measured as a function of temperature. Negative values of ΔH and ΔS were obtained for the transfer of mefloquine from the aqueous to the gel phase of the phospholipid. The partitioning is enthalpy controlled which suggests that mefloquine interacts strongly with the phospholipid phase. In contrast, the partitioning of mefloquine into the liquid crystalline phase of DMPC is entropy controlled which is typical of a hydrophobic interaction between mefloquine and the aqueous phase. The partitioning of mefloquine into the bulk solvents octanol and hexane were found to be enthalpy and entropy controlled, respectively. The enthalpy dominated partitioning of mefloquine into gel phase DMPC and octanol is attributed to the occurrence of hydrogen bonding and van der Waals interactions between solute and solvent. The flat shape of mefloquine may further its interaction with the orderly domains of the lipidic/organic phase. This is apparent from a comparison of the partitioning characteristics of another structurally related but conformationally different molecule, quinine into DMPC and octanol.

• 公益社団法人日本薬学会の論文
• 1997-12-15

著者

• Go Mei-lin

  Department Of Pharmacy National University Of Singapore

• Ngiam Tong-lan

  Department Of Pharmacy National University Of Singapore

関連論文

• Interaction of the Antimalarial Agents Halofantrine and Lumefantrine with Lipid Bilayers
• Synthesis, Antimuscarinic Activity and Quantitative Structure-Activity Relationship (QSAR) of Tropinyl and Piperidinyl Esters
• Pharmacological Activity and Structure-Activity Relationship of (±)-erythro-Mefloquine and Related Compounds on the Isolated Mouse Phrenic Nerve Diaphragm Preparation
• The Antimalarial Agent Halofantrine Perturbs Phosphatidylcholine and Phosphatidylethanolamine Bilavers : a Differential Scanning Calorimetric Study
• Structure-Hydrolyzability Relationships in a Series of Piperidinyl and Tropinyl Esters with Antimuscarinic Activity
• Halofantrine-Phospholipid Interactions : Monolayer Studies
• Molecular Geometry and Physicochemical Characteristics of Selected Anilinoquinolines, Indolo[3,2-c]quinolines and Tetrahydroindolo[3,2-d]benzazepines
• Thermodynamics of Partitioning of the Antimalarial Drug Mefloquine in Phospholipid Bilayers and Bulk Solvents
• A Differential Scanning Calorimetry Study of the Interaction of the Antimalarial Agent Halofanthrine with Dipalmitoyl Phosphatidyl Choline Bilayers
• Thermodynamics of the Partitioning of 7-Chloro-4-(4'-methoxy)antilinoquinoline and Its Cyclized Analog in Octanol-Buffer and Liposome Systems

スポンサーリンク