NDLI: The evidence for complex formation between N-acetyl-l-tyrosine methyl ester and N-acetylprocainamide hydrochloride using NMR spectroscopy

Content Provider	Springer Nature Link
Author	Janik, Alicja Bukowska, Marta Jamroży, Krzysztof Stadnicka, Katarzyna
Copyright Year	2009
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.
Starting Page	699
Ending Page	707
Page Count	9
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	20
Issue Number	4
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2009-05-05
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	NMR spectroscopy Complex formation Protected l-tyrosine N-acetylprocainamide hydrochloride Theoretical and Computational Chemistry Physical Chemistry Computer Applications in Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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