Thermodynamics of partitioning of the antimalarial drug mefloquine in phospholipid bilayers and bulk solvents

Chemical & Pharmaceutical Bulletin
M L Go, T L Ngiam

Abstract

The antimalarial drug mefloquine binds avidly to phospholipids in biomembranes. The thermodynamics of the partitioning process in dimyristoylphosphatidylcholine (DMPC) bilayers was investigated to give some 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 delta H and delta S 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 aid its interac...Continue Reading

Citations

Oct 31, 2013·Pharmaceutical Research·Lívia Palmerston MendesEliana Martins Lima
Feb 13, 2010·Malaria Journal·Erin MilnerGeoffrey Stuart Dow
Aug 23, 2005·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Alfred FahrMathew L S Leigh
Mar 4, 2003·Chemical & Pharmaceutical Bulletin·Carolina Mercedes Avila, Fleming Martínez
Dec 16, 2016·The Journal of Physical Chemistry. B·Bradley A RogersYanjie Zhang

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antimalarial Agents

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.

Antimalarial Agents (ASM)

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.