Synthesis and biological evaluation of a pyoverdin-β-lactam conjugate: A new type of arginine-specific cross-linking in aqueous solution

Journal of Peptide Research

Volumn 53, Issue 6, 1999, Pages 618-625

  Kinzel, O ^b   Budzikiewicz, H ^a  

^a Institute of Organic Chemistry   (Germany)

^b NONE

Author keywords

Arginine specific cross linking; Derivatization of arginine residues; Drug transport; Pseudomonas aeruginosa; Pyoverdin lactam conjugate

Indexed keywords

CEFALEXIN; CEPHALOSPORIN DERIVATIVE; N 4,6 DIOXOHEPTANOYLCEPHALEXIN; PYOVERDIN D CEPHALEXIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CELL TRANSPORT; CROSS LINKING; DRUG CONFORMATION; DRUG POTENTIATION; DRUG SYNTHESIS; DRUG UPTAKE; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STRUCTURE ACTIVITY RELATION;

ACYLATION; ARGININE; BETA-LACTAMS; CELL DIVISION; CEPHALEXIN; CROSS-LINKING REAGENTS; HEPTANOATES; IRON CHELATING AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; OLIGOPEPTIDES; PIGMENTS, BIOLOGICAL; PSEUDOMONAS AERUGINOSA; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 0033049572     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00053.x     Document Type: Article

References (15)

1. 1. Yankeelov, J.A. Jr (1972) Modification of arginine by diketones. Methods Enzymol. 25, 566-579.
2. 2. Ngo, T.T., Yam, C.F., Lenhoff, H.M. & Ivy, J. (1981) p-Azidophenylglyoxal, a heterobifunctional photoactivable cross-linking reagent selective for arginyl residues. J. Biol. Chem. 256, 11313-11318.
3. 3. Duerksen, P.J. & Wilkinson, K.D. (1987) Immobilization of proteins via arginine residues. Anal. Biochem. 160, 444-454.
4. 4. Takahashi, K. (1968) The reaction of phenylglyoxal with arginine residues in proteins. J. Biol. Chem. 243, 6171-6179.
5. 5. Krell, T., Chackrewarthy, S., Pitt, A.R., Elwell, A. & Coggins, J.R. (1998) Chemical modification monitored by electrospray mass spectrometry: a rapid and simple method for identifying and studying functional residues in enzymes. J. Peptide Res. 51, 201-209.
6. 6. Kinzel, O., Tappe, R., Gerus, L & Budzikiewicz, H. (1998) The synthesis and antibacterial activity of two pyoverdin-ampicillin conjugates, entering Pseudomonas aeruginosa via the pyoverdin-mediated iron uptake pathway. J. Antibiot. 51, 499-507.
7. 7. Budzikiewicz, H. (1997) Siderophores from fluorescent Pseudomonas. In: Studies in Natural Products Chemistry 19 (Atta-Ur-Rahman, ed.). Elsevier, Amsterdam, pp. 793-835.
8. 8. Meyer, J.M., Hohnadel, D., Khan, A. & Cornelis, P. (1990) Pyoverdin-facilitated iron uptake in Pseudomonas aeruginosa: immunological characterization of the ferripyoverdin receptor. Mol. Microbiol. 4, 1401-1405.
9. 9. Meyer, J.M., Stintzi, A., De Vos, D. et al. (1997) Use of siderophores to type pseudomonads: the three Pseudomonas aeruginosa pyoverdine systems. Microbiology 143, 35-43.
10. 10. Briskot, G., Taraz, K. & Budzikiewicz, H. (1986) Pyoverdin-type siderophores from Pseudomonas aeruginosa. Z. Naturforsch. 410, 497-506.
11. 11. Gilbert, H.F. & O'Leary, M.H. (1975) Modification of arginine and lysine in proteins with 2,4-pentanedione. Biochemistry 14, 5194-5199.
12. 12. Beller, P., Van Thuong, T. & Nomine, G. (1968) French patent 1,468,831; Chem. Abstr. 68, 22257v.
13. 13. Yamana, T. & Tsuji, A. (1976) Comparative stability of cephalosporins in aqueous solution: kinetics and mechanisms of degradation. J. Pharm. Sci. 65, 1563-1574.
14. 14. Cornelis, P., Hohnadel, D. & Meyer, J.M. (1989) Evidence for different pyoverdin-mediated iron-uptake systems among Pseudomonas aeruginosa strains. Infect. Immun. 57, 3491-3497.
15. 15. Pendarvis, R.O. & Hampton, K.G. (1974) Synthesis of dioxocarboxylic acids. J. Org. Chem. 39, 2289-2291.