The evidence for complex formation between N-acetyl-l-tyrosine methyl ester and N-acetylprocainamide hydrochloride using NMR spectroscopy |
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Authors: | Alicja Janik Marta Bukowska Krzysztof Jamroży Katarzyna Stadnicka |
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Institution: | (1) Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland |
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Abstract: | In order to reveal the possible mechanism of the recognition of antiarrhythmic agents class I and class III by the amino acid
residues, which are responsible for drug binding to the selectivity filters either in the sodium or potassium ion channels,
co-crystallizations of procainamide hydrochloride and N-acetylprocainamide hydrochloride with N-acetyl-l-tyrosine methyl ester and N-acetyl-l-phenylalanine methyl ester were performed using various conditions. Because the crystallization of the complexes failed, the
intermolecular interactions between the components were evidenced using NMR spectroscopy. Exclusively, in the case of N-acetylprocainamide hydrochloride and N-acetyl-l-tyrosine methyl ester, two-dimensional NMR experiments and Job Plot analysis indicated the formation of the 1:1 complex in
DMSO-d
6
solution (with the association constant of 16 M−1), whereas for the mixture of procainamide hydrochloride with N-acetyl-l-tyrosine methyl ester, the complex formation was not confirmed. The NMR results were discussed using crystal structure data
obtained for N-acetylprocainamide hydrochloride, procainamide hydrochloride, as well as procainamide dihydrochloride, and were compared
with the known pharmacological activity of the antiarrhythmic agents. |
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Keywords: | NMR spectroscopy Complex formation l-tyrosine" target="_blank">Protected l-tyrosine N-acetylprocainamide hydrochloride |
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