{"title":"Fatty Alcohol Membrane Model for Quantifying and Predicting Amphiphilicity.","authors":"Nur Afiqah Ahmad, Junming Ho","doi":"10.1021/acs.jcim.4c01615","DOIUrl":null,"url":null,"abstract":"<p><p>Amphiphilicity is an important property for drug development and self-assembly. This paper introduces a general approach based on a simple fatty alcohol (dodecanol) membrane model that can be used to quantify the amphiphilicity of small molecules that are in good agreement with experimental surface tension data. By applying the model to a systematic series of compounds, it was possible to elucidate the effect of different motifs on amphiphilicity. The results further indicate that amphiphilicity correlates strongly with water-octanol partition coefficients (log<i>P</i>) for the 29 organic molecules examined in the 0 < log<i>P <</i> 4 range. Importantly, the simulation of the model membrane is an order of magnitude faster than a phospholipid membrane (e.g., 1-palmitoyl-2-oleoyl-<i>sn</i>-glycero-3-phosphocholine) simulation and offers a simple atomistic approach for quantifying and predicting amphiphilicity of small drug-like molecules that could be used in quantitative structure-activity relationship studies.</p>","PeriodicalId":44,"journal":{"name":"Journal of Chemical Information and Modeling ","volume":" ","pages":""},"PeriodicalIF":5.6000,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Information and Modeling ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.jcim.4c01615","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
Amphiphilicity is an important property for drug development and self-assembly. This paper introduces a general approach based on a simple fatty alcohol (dodecanol) membrane model that can be used to quantify the amphiphilicity of small molecules that are in good agreement with experimental surface tension data. By applying the model to a systematic series of compounds, it was possible to elucidate the effect of different motifs on amphiphilicity. The results further indicate that amphiphilicity correlates strongly with water-octanol partition coefficients (logP) for the 29 organic molecules examined in the 0 < logP < 4 range. Importantly, the simulation of the model membrane is an order of magnitude faster than a phospholipid membrane (e.g., 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) simulation and offers a simple atomistic approach for quantifying and predicting amphiphilicity of small drug-like molecules that could be used in quantitative structure-activity relationship studies.
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The Journal of Chemical Information and Modeling publishes papers reporting new methodology and/or important applications in the fields of chemical informatics and molecular modeling. Specific topics include the representation and computer-based searching of chemical databases, molecular modeling, computer-aided molecular design of new materials, catalysts, or ligands, development of new computational methods or efficient algorithms for chemical software, and biopharmaceutical chemistry including analyses of biological activity and other issues related to drug discovery.
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