期刊
JOURNAL OF CHEMICAL INFORMATION AND MODELING
卷 60, 期 2, 页码 569-577出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jcim.9b00830
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资金
- FAPERJ [210.558/2015, E-26/010.001241/2016]
- CNPq [465259/2014-6, 302554/2017-3]
- CAPES [001]
- FAPESP [2014/50983-3]
- National Institute of Science and Technology Complex Fluids (INCT-FCx)
The lipophilicity of cholesterol was investigated by using coarse-grained molecular dynamics and umbrella sampling. The previous coarse-grained cholesterol models in the literature are more hydrophobic than our model. The Gibbs free energy of transferring cholesterol from the octanol phase to water phase (Delta G(o/w)) was 11.88 +/- 0.08 kcal mol(-1), and the octanol-water partitioning coefficient (logP) was estimated to be 8.72 +/- 0.06. The latter is in agreement with the logP values found by bioinformatics, which are standard methods to predict the lipophilicity, giving excellent octanol/water partitioning coefficients compared with experimental ones for different molecules. We also performed the first experimentally direct measurement of this important property for cholesterol. The experimental octanol/water partitioning coefficient of cholesterol was measured to be 8.86 +/- 0.79, which is in excellent agreement with our calculated logP value from our parametrized coarse-grained cholesterol model. This shows the significance of systematic optimization of the lipophilicity for developing coarse-grain models of important biomolecules with complicated molecular structures and hydrophobic character like cholesterol.
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