Activation Thermodynamic Quantities for the Release of 3-Aminopyridine (3AP) from Fatty Acid-3AP Equimolar Complexes

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The rates of release of 3-aminopyridine (3AP) from fatty acid (FA)-3AP complexes, FA-3AP, were determined at various temperatures, and the thermodynamic quantities of the release of 3AP were estimated. The results were compared with previous results obtained for FA-nicotinamide (NAA) complexes, FA-NAA.The values of activation enthalpy (ΔH^〓) and activation entropy (ΔS^〓) for the release of 3AP from FA-3AP were positive and negative, respectively, indicating that the release of 3AP is disadvantageous from not only enthalpic but also entropic viewpoints. The plots of ΔH^〓 against the carbon number (n) in the constituent FA showed a zig-zag line with an upward convex at odd-numbered positions and the plots of the absolute values of |-ΔS^〓| showed a zig-zag line with a downward convex at odd-numbered positions, though the positive value of ΔH^〓 increased and the negative ralue of ΔS^〓 decreased with an increasing n for either even-numbered or odd-numbered FA. It was found that the release of 3AP from RA-3AP formed with odd-numbered FA is more disadvantageous enthalpically but more advantageous entropically as compared with that from FA-3AP formed with even-numbered FA. Furthermore, it is suggested that FA-3AP is formed by at least van der Waals forces and hydrophobic interactions.It was found that FA-3AP has similar physicochemical properties to FA-NAA and that the variation in physico-chemical properties of FA-3AP owing to the difference in n is smaller than that of FA-NAA. This is considered to be due to the fact that the packing of 3AP into the FA host cavity is looser than that of NAA.
公益社団法人日本薬学会の論文
1993-10-15

Activation Thermodynamic Quantities for the Release of 3-Aminopyridine (3AP) from Fatty Acid-3AP Equimolar Complexes

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