The distribution of substituted phenols into lipid vesicles

Davis, S.S.; James, Michael J.; Anderson, Nicholas H.

doi:10.1039/dc9868100313

Cited by 19 publications

(16 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In a previous study, the thermodynamic parameters for the partitioning of a series of phenols and anisoles into DMPC have been determined (29). The compounds studied were chosen to investigate the effects of alkyl chain length, size of the substituent groups, substituent position on the aromatic ring, and the effect of hydrogen bonding groups within the molecules.…”

Section: Isothermal Titration Calorimetry (Itc) Studiesmentioning

confidence: 99%

The Thermodynamics of the Partitioning of Ionizing Molecules Between Aqueous Buffers and Phospholipid Membranes

et al. 2005

View full text Add to dashboard Cite

show abstract

Section: Isothermal Titration Calorimetry (Itc) Studiesmentioning

confidence: 99%

The Thermodynamics of the Partitioning of Ionizing Molecules Between Aqueous Buffers and Phospholipid Membranes

et al. 2005

View full text Add to dashboard Cite

show abstract

“…The opposite was observed by Davis et al, who measured the partitioning into gel state membranes. 41 The volume fraction profiles of the additives of Fig. 6 do not contain many surprises.…”

Section: B Partition Coefficients Of Alcoholsmentioning

confidence: 99%

Self-consistent-field modeling of complex molecules with united atom detail in inhomogeneous systems. Cyclic and branched foreign molecules in dimyristoylphosphatidylcholine membranes

Meijer

Leermakers

Lyklema

1999

The Journal of Chemical Physics

View full text Add to dashboard Cite

We have developed a detailed self-consistent-field model for studying complex molecules in inhomogeneous systems, in which all the molecules are represented in a detailed united atom description. The theory is in the spirit of the approach developed by Scheutjens and co-workers for polymers at interfaces and self-assembly of surfactants and lipids into association colloids. It is applied to lipid membranes composed of dimyristoylphosphatidylcholine ͑DMPC͒. In particular, we looked at the incorporation of linear, branched, and cyclic molecules into the lipid bilayers being in the liquid phase. Detailed information on the properties of both the lipids and the additives is presented. For the classes of linear and branched alcohols and phenol derivatives we find good correspondence between calculated partition coefficients for DMPC membranes and experimental data on egg-yolk PC. The calculated partitioning of molecules of isomers, containing a benzene ring, two charged groups ͑one positive and one negative͒ and 16 hydrocarbon segments, into DMPC membranes showed variations of the partition coefficient by a factor of 10 depending on the molecular architecture. For zwitterionic additives we find that it is much more difficult to bring the positive charge into the membrane core than the negative one. This result can be rationalized from information on the electrostatic potential profile of the bare membrane, being positive in both the core and on the membrane surface but negative near the position of the phosphate groups. For several tetrahydroxy naftalenes we found that, although the partition coefficient is barely influenced, the average orientation and position of the molecule inside the membrane is strongly dependent on the distribution of the hydroxyl groups on the naphthalene rings. The orientation changes from one where the additive spans the membrane when the hydroxyls are positioned on ͑2,3,6,7͒ positions, to an orientation with the rings parallel to the membrane surface and located near the head grouphydrophobic core interface for the hydroxyls at the ͑1,3,5,7͒ positions. We propose that, when our model is used in combination with octanol/water partitioning data, a very accurate prediction is possible of the affinity of complex molecules for lipid membranes.

show abstract

“…A remarkable change in partitioning of solute in membrane lipids can occur on liposomes passing through their melting point or phase main transition temperature T, (12,18). Below T,, membrane lipids are in the gel phase, and above T,, they are in the liquid crystalline phase.…”

Section: Introductionmentioning

confidence: 99%

“…It is believed that general anesthetic toxicological effects of hydrophobic compounds are the result of compound-membrane interactions (9,10). The biochemical aspects of these interactions are poorly understood, but it is suggested that hydrophobics inserted in the membrane can alter the membrane fluidity and so interfere with biological functions of the membrane (11,12).…”

Section: Introductionmentioning

confidence: 99%

Membrane-Water Partitioning of Polychlorinated Biphenyls in Small Unilamellar Vesicles of Four Saturated Phosphatidylcholines

Dulfer¹,

Govers²

1995

Environ. Sci. Technol.

View full text Add to dashboard Cite

The distribution of substituted phenols into lipid vesicles

Cited by 19 publications

References 3 publications

The Thermodynamics of the Partitioning of Ionizing Molecules Between Aqueous Buffers and Phospholipid Membranes

The Thermodynamics of the Partitioning of Ionizing Molecules Between Aqueous Buffers and Phospholipid Membranes

Self-consistent-field modeling of complex molecules with united atom detail in inhomogeneous systems. Cyclic and branched foreign molecules in dimyristoylphosphatidylcholine membranes

Membrane-Water Partitioning of Polychlorinated Biphenyls in Small Unilamellar Vesicles of Four Saturated Phosphatidylcholines

Contact Info

Product

Resources

About