Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules

European Journal of Pharmaceutical Sciences

Volumn 32, Issue 1, 2007, Pages 1-7

  Kóczián, Kristóf ^a   Szakács, Zoltán ^b   Kökösi, József ^a   Noszál, Béla ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

6 Aminopenicillanic acid; 7 Aminocephalosporanic acid; Microscopic protonation constant; Microspeciation; NMR pH titration

Indexed keywords

6 AMINOPENICILLANIC ACID; 7 AMINOCEPHALOSPORANIC ACID; AMPHOLYTE; BETA LACTAM; ESTER DERIVATIVE;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; POTENTIOMETRIC TITRATION; PRIORITY JOURNAL; PROTON TRANSPORT;

BETA-LACTAMS; CEPHALOSPORINS; HYDROGEN-ION CONCENTRATION; IONS; MAGNETIC RESONANCE SPECTROSCOPY; OSMOLAR CONCENTRATION; PENICILLANIC ACID; PENICILLINS; POTENTIOMETRY; PROTONS;

EID: 34548678681     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2007.05.001     Document Type: Article

References (33)

1. Arndt F. Nitrosomethylurea. 1. From methylamine hydrochloride. Org. Synth. 2 (1943) 461-462
2. Arndt F. Preparation of diazomethane. Org. Synth. 2 (1943) 165-167
3. Basso A., Biffi S., Martin L.D., Gardossi L., and Linda P. Quantitative acylation of amino compounds catalysed by penicillin G acylase in organic solvent at controlled water activity. Croat. Chem. Acta 74 (2001) 757-762
4. Berezin I.V., Klyesov A.A., Margolin A.L., Nys P.S., Savitskaya E.M., and Shvyadas V.K. Study of penicillin amidase from E. coli. The pH-dependence of the equilibrium constant of the enzymic hydrolysis of benzylpenicillin. Antibiotiki 21 (1976) 519-523
5. Bowden K., and Bromley K. Reactions of carbonyl-compounds in basic solutions .15. The alkaline-hydrolysis of n-methyl, n-phenyl and bicyclo lactams, penicillins and n-alkyl-n-methylacetamides. J. Chem. Soc., Perkin Trans. 2 12 (1990) 2111-2116
6. Boyd D.B. Substituent effects in cephalosporins as assessed by molecular-orbital calculations, nuclear magnetic-resonance, and kinetics. J. Med. Chem. 26 (1983) 1010-1013
7. Chopra I. Approaches for the discovery of new antibacterial agents. Culture 20 (1999) 3-6
8. Demarco P., and Nagarayan Y. Penicillins and Cefalosporins, Chemistry and Biology (1972), Academic Press, New York p. 312 (table of C. Oniscu)
9. Dürckheimer W., and Schorr M. N-Alkylderivate der 6-Amino-penicillansäure. Liebigs Ann. Chem. 702 (1967) 163-168
10. Frassineti C., Ghelli S., Gans P., Sabatini A., Moruzzi M.S., and Vacca A. Nuclear-magnetic-resonance as a tool for determining protonation constants of natural polyprotic bases in solution. Anal. Biochem. 231 (1995) 374-382
11. Frau J., Donoso J., Munoz F., Vilanova B., and Garcia-Blanco F. Study of the alkaline hydrolysis of the azetidin-2-one ring by ab initio methods: influence of the solvent. Helv. Chim. Acta 80 (1997) 739-747
12. Hoult D.I. Solvent peak saturation with single-phase and quadrature fourier transformation. J. Magn. Reson. 21 (1976) 337-347
13. Kanazawa K., Nouda H., and Sunagawa M. Structure-activity relationships of carbapenem compounds to anti-Haemophilus influenzae activity and affinity for penicillin-binding proteins effect of 1 beta-methyl group and C-2 side chain. J. Antibiot. 50 (1997) 162-168
14. Knowles D.J.C. New strategies for antibacterial drug design. Trends Microbiol. 5 (1997) 379-383
15. Kyvala, M., Lukes, I., 1995. Chemometrics '95, Pardubice, Book of Abstracts 63. http://www.natur.cuni.cz/∼kyvala/opium.html.
16. Micetich R.G., Singh R., and Shaw C.C. Oxidation studies on beta-lactam antibiotics-the 6-(diacylamino)penicillins. J. Org. Chem. 51 (1986) 1811-1815
17. Noszál B. Acid-base properties of bioligands. In: Burger K. (Ed). Biocoordination Chemistry: Coordination Equilibria in Biologically Active Systems (1990), Ellis Horwood, Chichester 18-55
18. Page M.I. The mechanisms of reactions of beta-lactam antibiotics. Adv. Phys. Org. Chem. 23 (1987) 165-270
19. Proctor P., Gensmantel N.P., and Page M.I. The chemical-reactivity of penicillins and other beta-lactam antibiotics. J. Chem. Soc., Perkin Trans. 2 9 (1982) 1185-1192
20. Rapson H.D.C., and Bird A.E. Ionisation constants of some penicillins and of their alkaline and penicillinase hydrolysis products. J. Pharm. Pharmacol. 15 (1963) 222-231
21. Richardson F.S., Yeh C.Y., Troxell T.C., and Boyd D.B. Electronic-structures of cephalosporins and penicillins. 6. Studies on circular-dichroism of penam and penam sulfoxides. Tetrahedron 33 (1977) 711-721
22. a, P(ion), P(neutral)] of acids and bases by nonlinear regression analysis of pH-dependent partition measurements. J. Chem. Res. (S) 11 (1979) 357
23. Schobert R., and Stangl A. Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO. Tetrahedron Lett. 46 (2005) 1127-1130
24. Schwarz M.A., and Wu G.M. Kinetics and reactions involved in penicillin allergy I Mechanism of reaction of penicillins and 6-aminopenicillanic acid with glycine in alkaline solution. J. Pharm. Sci. 55 (1966) 550-555
25. Scifinder data calculated by using Advanced Chemistry Development (ACD/Labs) Software V8.14 for Solaris ((C) 1994-2007 ACD/Labs).
26. Shehata M.R., Shoukry M.M., and Barakat M.H. Coordination properties of 6-aminopenicillanic acid: binary and ternary complexes involving biorelevant ligands. J. Coord. Chem. 57 (2004) 1369-1386
27. Smith R.S., and Martell A.E. Critical Stability Constants (1975), Plenum Press, New York
28. Szakács Z., Hägele G., and Tyka R. H-1/P-31 NMR pH indicator series to eliminate the glass electrode in NMR spectroscopic pK(a) determinations. Anal. Chim. Acta 522 (2004) 247-258
29. Szakács Z., Kraszni M., and Noszál B. Determination of microscopic acid-base parameters from NMR-pH titrations. Anal. Bioanal. Chem. 378 (2004) 1428-1448
30. Szakács Z., Béni Sz., Varga Z., O{combining double acute accent}rfi L., Kéri Gy., and Noszál B. Acid-base profiling of imatinib (Gleevec) and its fragments. J. Med. Chem. 48 (2005) 249-255
31. Therrien C., Kotra L.P., Sanschagrin F., Mobashery S., and Levesque R.C. Evaluation of inhibition of the carbenicillin-hydrolyzing beta-lactamase PSE-4 by the clinically used mechanism-based inhibitors. FEBS Lett. 470 (2000) 285-292
32. Tsuji A., Nakashima E., Deguchi Y., Nishide K., Shimizu T., Horiuchi S., Ishikawa S., and Yamana T. Degradation kinetics and mechanism of aminocephalosporins in aqueous-solution-cefadroxil. J. Pharm. Sci. 70 (1981) 1120-1128
33. Wagner U.G., Petersen E.I., Schwab H., and Kratky C. EstB from Burkholderia gladioli: a novel esterase with a beta-lactamase fold reveals steric factors to discriminate between esterolytic and beta-lactam cleaving activity. Protein Sci. 11 (2002) 467-478