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Interaction of indole derivatives with immobilized 3, 5-dinitrobenzoyl-phenylglycine

Relative binding constants for 50 ring-substituted indolic compounds, most of them with auxin activity, to immobilized 3, 5-dinitrobenzoyl-phenylglycine were determined by high performance liquid chromatography. To learn more about the recognition mechanism, QSPR (quantitative structure-property relationship) analysis was performed. A five-parameter model, based on physico-chemical and structural properties, was obtained which accounted for more than 97% of the variations in the relative binding constants. The robustness of the model was confirmed by internal (q2LOO = 0.952) and external (q2EXT = 0.900) validation. The model suggests that the binding constants of indole derivatives are mainly governed by the electronic and steric properties of the substituents at the indole nucleus. Electron-donating substituents increased affinity, while electron-withdrawing substituents decreased it. Substituents which can form hydrogen-bonds with the acceptor phase further strengthened affinity, while the negative effect of bulky substituents could be ascribed to steric restrictions at the acceptor phase. The relative binding constants of the dihalogenated compounds studied were essentially determined by their substitution patterns.

indole derivatives ; 3 ; 5-dinitrobenzoyl-phenylglycine ; high-performance liquid chromatography ; quantitative structure-property relationships

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