The 4-fluorophenylbiguanide (4-FPBG) is related to antimalarial drugs of which the drug penetration is an important aspect of mode of action. Furthermore, it is related to 1- phenylbiguanide (PBG) interacts with membrane like interfaces and was characterized using a reverse micelle (RM) model system in our laboratory1. In this work, we used not only 1H-NMR to study the interaction of 4-FPBG with reverse micelles (RMs) but also used 19F-NMR. The spectral changes are a sensitive probe of the properties of 4-FPBG and as the RMs are varied the interaction of the compound can change and will be reflected in the chemical shifts of the compound. For example, the chemical shift both of all 4-FPBG that clearly confirm the form of compound is that in the deprotonated and mono-protonated forms. The 1H NMR and 19F-NMR studies demonstrated that the 4-FPBG compound in an aqueous environment changed from the aqueous environment to an interfacial environment when placed in the model membrane system. The signals for the deprotonated form are 0.05 to 0.20 ppm downfield from the mono-protonated form that exists in solutions at pH 2 through 9. In summary, we found that 4-FPBG show similar changes as the PBG which were found to interact with different regions of the interface, with the phenyl group penetrating the hydrophobic interface while the biguanide remains in the water pool.

1H- and 19F-NMR spectroscopic studies of 4-fluorophenylbiguanide with the interface of reverse micelles

249th National Meeting (2015)

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