Fluorophilicity of Alkyl and Polyfluoroalkyl 1 Nicotinic Acid Ester Prodrugs.

ABSTRACT: 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 preferential

SUBMITTER: Ojogun V 

PROVIDER: S-EPMC2887708 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature