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Experimental and computational study of membrane affinity for selected energetic compounds.

Anastasiia Golius¹, Leonid Gorb², Andrea Michalkova Scott³

¹Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS, USA.

|January 29, 2016

Summary

Energetic compounds like TNT show moderate membrane penetration. Liposome-water partition coefficients (log(Klipw)) were generally higher than octanol-water partition coefficients (log(Kow)) for these compounds.

Keywords:

Artificial bilayer lipid membranes Energetic compounds Partition coefficient Theoretical study

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Published on: February 21, 2019

Area of Science:

Environmental Chemistry
Computational Chemistry
Biophysics

Background:

Understanding the interaction of energetic compounds with biological membranes is crucial for assessing their environmental fate and toxicological impact.
Partition coefficients, such as octanol-water (log(Kow)) and liposome-water (log(Klipw)), are key parameters for predicting compound behavior in biological systems.

Purpose of the Study:

To investigate the affinity of various energetic compounds for biological membranes.
To compare experimental and computational methods for determining membrane partition coefficients.
To evaluate the membrane penetration potential of compounds including trinitrotoluene (TNT).

Main Methods:

Experimental measurement of octanol-water (log(Kow)) and liposome-water (log(Klipw)) partition coefficients.
Utilized artificial solid-supported lipid liposomes (TRANSIL) for log(Klipw) determination.
Computational prediction of log(Kow) using program packages (e.g., COSMOthermX) and log(Klipw) using COSMOmic.

Main Results:

Partition coefficients were determined for TNT, dinitrotoluene isomers, dinitroanisole, methoxynitrophenol, trinitrobenzene, and dinitrophenol.
Experimental and computational log(Klipw) and log(Kow) values were obtained.
A moderate ability for the studied energetic compounds to penetrate membranes was observed.
Generally, log(Kow) values were found to be slightly lower than log(Klipw) values.

Conclusions:

The energetic compounds investigated exhibit moderate membrane permeability.
The study validates the use of both experimental and computational approaches for assessing membrane affinity.
Findings contribute to a better understanding of the environmental behavior and potential bioaccumulation of energetic materials.