| Fluorophilicity of Alkyl and Polyfluoroalkyl 1 Nicotinic Acid Ester Prodrugs. | |
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MedLine Citation:
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PMID: 20567608 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The fluorophilicity of a series of hydrocarbon and fluorocarbon-functionalized nicotinic acid esters (nicotinates) is measured from their partitioning behavior (log K(P)) in the biphasic solvent system of perfluoro(methylcyclohexane) (PFMC) and toluene. The chain length of the hydrocarbon or fluorocarbon alkyl group of the ester ranges from one to twelve carbon atoms. Knowledge of the fluorophilicity of these solutes is relevant to the design of these prodrugs for fluorocarbon-based drug delivery. The experimental log K(p) values range from -1.72 to -3.40 for the hydrocarbon nicotinates and -1.64 to 0.13 for the fluorinated nicotinates, where only the prodrug with the longest fluorinated chain (2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl nicotinic acid ester) partitions preferentially into the fluorinated phase (log K(p) = 0.13). Predictions of the partition coefficients using solubility parameters calculated from group contribution techniques or molecular dynamics simulation are in reasonable agreement for the perhydrocarbon nicotinates and short chained perfluorinated nicotinates ( approximately 0.3%-39% deviation). Significant deviations from experimental partition coefficients (greater than 100%) are observed for the longest chain perfluoroalkyl nicotinates. |
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Authors:
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Vivian Ojogun; Barbara L Knutson; Sandhya Vyas; Hans-Joachim Lehmler |
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Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: Journal of fluorine chemistry Volume: 131 ISSN: 0022-1139 ISO Abbreviation: - Publication Date: 2010 Jul |
Date Detail:
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Created Date: 2010-7-13 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0373322 Medline TA: J Fluor Chem Country: - |
Other Details:
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Languages: ENG Pagination: 784-790 Citation Subset: - |
Affiliation:
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Chemical and Materials Engineering Department 177 Anderson Hall, University of Kentucky, Lexington, KY 40506-0046. |
Export Citation:
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Descriptor/Qualifier:
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| Grant Support | |
ID/Acronym/Agency:
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R21 EB002748-01//NIBIB NIH HHS; R21 EB002748-02//NIBIB NIH HHS |
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