Journal
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
Volume 59, Issue -, Pages 78-82Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.jpba.2011.10.009
Keywords
Streptomycin; NMR-pH titration; Highly basic media; Microspeciation; Microscopic acid-base properties
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Funding
- OTKA [T 73804]
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Streptomycin, the classical aminoglycoside antibiotic, generally considered the most basic drug compound was characterized in terms of protonation macro- and microconstants. H-1 NMR-pH and H-1-C-13 HSQC-pH titrations were carried out on streptomycin and streptidine, a symmetrical constituent compound of reduced complexity to monitor the proton-binding processes of the basic sites. Accurate, undistorted, electrodeless pH measurement was ensured by a new set of in tube indicators. The microscopic protonation constants of the two guanidino groups of streptomycin were calculated by evaluating the various NMR-pH data and transferring the pair-interactivity parameter from streptidine to streptomycin. Inherent guanidino basicities fall in the range of 13.03-13.39 log k units, which drop to 12.48-12.85 upon protonation of the other site. pH-dependent distribution of the major microspecies and charge-related biological consequences are provided. (C) 2011 Elsevier BM. All rights reserved.
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