Alejandro Fernández-Pumarega, Belén Martín-Sanz, Susana Amézqueta, Elisabet Fuguet, Martí Rosés
{"title":"利用阳离子微乳液电动色谱系统估算碱性化合物的辛醇-水分配系数。","authors":"Alejandro Fernández-Pumarega, Belén Martín-Sanz, Susana Amézqueta, Elisabet Fuguet, Martí Rosés","doi":"10.5599/admet.760","DOIUrl":null,"url":null,"abstract":"<p><p>The octanol-water partition coefficient (P<sub>o/w</sub>), or the octanol-water distribution coefficient (D<sub>o/w</sub>) for ionized compounds, is a key parameter in the drug development process. In a previous work, this parameter was estimated through the retention factor measurements in a sodium dodecyl sulfate (SDS) - microemulsion electrokinetic chromatography (MEEKC) system for acidic compounds. Nonetheless, when ionized basic compounds were analyzed, undesirable ion pairs were formed with the anionic surfactant and avoided a good estimation of log D<sub>o/w</sub>. For this reason, an alternative MEEKC system based on a cationic surfactant has been evaluated to estimate P<sub>o/w</sub> or D<sub>o/w</sub> of neutral compounds and ionized bases. To this end, it has been characterized through the solvation parameter model (SPM) and compared to the octanol-water partition system. Results pointed out that both systems show a similar partition behavior. Hence, the log P<sub>o/w</sub> of a set of neutral compounds has been successfully correlated against the logarithm of the retention factor (log k) determined in this MEEKC system. Then, the log D<sub>o/w</sub> of 6 model bases have been estimated at different pH values and they have been compared to data from the literature, determined by the reference shake-flask and potentiometric methods. Good agreement has been observed between the literature and the estimated values when the base is neutral or partially ionized (up to 99% of ionization).</p>","PeriodicalId":14072,"journal":{"name":"International Journal of Environment and Pollution","volume":"37 1","pages":"98-112"},"PeriodicalIF":0.5000,"publicationDate":"2020-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8915598/pdf/","citationCount":"0","resultStr":"{\"title\":\"Estimation of the octanol-water distribution coefficient of basic compounds by a cationic microemulsion electrokinetic chromatography system.\",\"authors\":\"Alejandro Fernández-Pumarega, Belén Martín-Sanz, Susana Amézqueta, Elisabet Fuguet, Martí Rosés\",\"doi\":\"10.5599/admet.760\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The octanol-water partition coefficient (P<sub>o/w</sub>), or the octanol-water distribution coefficient (D<sub>o/w</sub>) for ionized compounds, is a key parameter in the drug development process. In a previous work, this parameter was estimated through the retention factor measurements in a sodium dodecyl sulfate (SDS) - microemulsion electrokinetic chromatography (MEEKC) system for acidic compounds. Nonetheless, when ionized basic compounds were analyzed, undesirable ion pairs were formed with the anionic surfactant and avoided a good estimation of log D<sub>o/w</sub>. For this reason, an alternative MEEKC system based on a cationic surfactant has been evaluated to estimate P<sub>o/w</sub> or D<sub>o/w</sub> of neutral compounds and ionized bases. To this end, it has been characterized through the solvation parameter model (SPM) and compared to the octanol-water partition system. Results pointed out that both systems show a similar partition behavior. Hence, the log P<sub>o/w</sub> of a set of neutral compounds has been successfully correlated against the logarithm of the retention factor (log k) determined in this MEEKC system. Then, the log D<sub>o/w</sub> of 6 model bases have been estimated at different pH values and they have been compared to data from the literature, determined by the reference shake-flask and potentiometric methods. Good agreement has been observed between the literature and the estimated values when the base is neutral or partially ionized (up to 99% of ionization).</p>\",\"PeriodicalId\":14072,\"journal\":{\"name\":\"International Journal of Environment and Pollution\",\"volume\":\"37 1\",\"pages\":\"98-112\"},\"PeriodicalIF\":0.5000,\"publicationDate\":\"2020-03-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8915598/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"International Journal of Environment and Pollution\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.5599/admet.760\",\"RegionNum\":4,\"RegionCategory\":\"环境科学与生态学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2020/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q4\",\"JCRName\":\"ENVIRONMENTAL SCIENCES\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"International Journal of Environment and Pollution","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.5599/admet.760","RegionNum":4,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2020/1/1 0:00:00","PubModel":"eCollection","JCR":"Q4","JCRName":"ENVIRONMENTAL SCIENCES","Score":null,"Total":0}
Estimation of the octanol-water distribution coefficient of basic compounds by a cationic microemulsion electrokinetic chromatography system.
The octanol-water partition coefficient (Po/w), or the octanol-water distribution coefficient (Do/w) for ionized compounds, is a key parameter in the drug development process. In a previous work, this parameter was estimated through the retention factor measurements in a sodium dodecyl sulfate (SDS) - microemulsion electrokinetic chromatography (MEEKC) system for acidic compounds. Nonetheless, when ionized basic compounds were analyzed, undesirable ion pairs were formed with the anionic surfactant and avoided a good estimation of log Do/w. For this reason, an alternative MEEKC system based on a cationic surfactant has been evaluated to estimate Po/w or Do/w of neutral compounds and ionized bases. To this end, it has been characterized through the solvation parameter model (SPM) and compared to the octanol-water partition system. Results pointed out that both systems show a similar partition behavior. Hence, the log Po/w of a set of neutral compounds has been successfully correlated against the logarithm of the retention factor (log k) determined in this MEEKC system. Then, the log Do/w of 6 model bases have been estimated at different pH values and they have been compared to data from the literature, determined by the reference shake-flask and potentiometric methods. Good agreement has been observed between the literature and the estimated values when the base is neutral or partially ionized (up to 99% of ionization).
期刊介绍:
IJEP provides an international forum in the field of environment and pollution and addresses early and medium-term challenges involving scientific prediction, modelling and assessment. It focuses on ground-breaking research in the science of environmental pollution, at the early scientific stage. It is one of three key journals which together offer complete coverage of environmental issues: IJETM focuses on technical/engineering, policy and management solutions for environmental problems, and IJGEnvI focuses on future, longer-term environmental scenarios, ecological economics, climate change and biodiversity.