A light-inactivated antibiotic

Journal of Medicinal Chemistry

Volumn 43, Issue 1, 2000, Pages 128-132

  Lee, Wenlin ^a   Li, Zhi Hong ^a   Vakulenko, Sergei ^a   Mobashery, Shahriar ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CEPHALOSPORIN DERIVATIVE; SODIUM 7BETA [2 (N 2 NITROBENZYLOXYCARBONYL)HYDRAZINO 3 PHENYLPROPANAMIDO]CEPHALOSPORANATE; UNCLASSIFIED DRUG;

ARTICLE; BACILLUS SUBTILIS; BACTERICIDAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; KLEBSIELLA PNEUMONIAE; LIGHT EXPOSURE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHOTODEGRADATION; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS;

BACTERIA; CARBAMATES; CEPHALOSPORINS; LIGHT; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; PHOTOCHEMISTRY;

EID: 0034642563     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980648a     Document Type: Article

References (30)

1. Levy, S. B. Antibiotic resistance: An Ecological Imbalance. In Antibiotic Resistance: Origins, Evolution, Selection and Spread; Chadwick, D. J., Goode, J., Eds.; Ciba Foundation Symposium 207; Wiley: Chichester, 1997; pp 1-14.
2. Levy, S. B. The Antibiotic Paradox. How Miracle Drugs Are Destroying the Miracle; Plenum Press: New York, 1992; pp 143-150.
3. Amit, B.; Zehavi, U.; Patchornik, A. Photosensitive Protecting Groups of Amino Sugars and Their Use in Glycoside Synthesis. 2-Nitrobenzyloxycarbonylamino and 6-Nitroveratryloxycarbonylamino Derivatives. J. Org. Chem. 1974, 39, 192-196. Patchornik, A.; Amit, B.; Woodward, R. B. Photosensitive Protecting Groups. J. Am. Chem. Soc. 1970, 6333-6335. Barltrop, J. A.; Plant, P. J.; Schofield, P. Photosensitive Protective Groups. Chem. Commun. 1966, 822-823.
4. Amit, B.; Zehavi, U.; Patchornik, A. Photosensitive Protecting Groups of Amino Sugars and Their Use in Glycoside Synthesis. 2-Nitrobenzyloxycarbonylamino and 6-Nitroveratryloxycarbonylamino Derivatives. J. Org. Chem. 1974, 39, 192-196. Patchornik, A.; Amit, B.; Woodward, R. B. Photosensitive Protecting Groups. J. Am. Chem. Soc. 1970, 6333-6335. Barltrop, J. A.; Plant, P. J.; Schofield, P. Photosensitive Protective Groups. Chem. Commun. 1966, 822-823.
5. Amit, B.; Zehavi, U.; Patchornik, A. Photosensitive Protecting Groups of Amino Sugars and Their Use in Glycoside Synthesis. 2-Nitrobenzyloxycarbonylamino and 6-Nitroveratryloxycarbonylamino Derivatives. J. Org. Chem. 1974, 39, 192-196. Patchornik, A.; Amit, B.; Woodward, R. B. Photosensitive Protecting Groups. J. Am. Chem. Soc. 1970, 6333-6335. Barltrop, J. A.; Plant, P. J.; Schofield, P. Photosensitive Protective Groups. Chem. Commun. 1966, 822-823.
6. -. J. Am. Chem. Soc. 1983, 105, 2481-2482. Klopman, G.; Fierson, M. R. The Alpha-Effect. A Theoretical Study Incorporating Solvent Effects. Croatica Chem. Acta 1984, 57, 1411-1415.
7. -. J. Am. Chem. Soc. 1983, 105, 2481-2482. Klopman, G.; Fierson, M. R. The Alpha-Effect. A Theoretical Study Incorporating Solvent Effects. Croatica Chem. Acta 1984, 57, 1411-1415.
8. -. J. Am. Chem. Soc. 1983, 105, 2481-2482. Klopman, G.; Fierson, M. R. The Alpha-Effect. A Theoretical Study Incorporating Solvent Effects. Croatica Chem. Acta 1984, 57, 1411-1415.
9. Page, M. I. The Mechanisms of Reactions of β-Lactam Antibiotics. Acc. Chem. Res. 1984, 17, 144-151. Page, M. I.; Laws, A. P. The Mechanism of Catalysis and The Inhibition of β-Lactamases. Chem. Commun. 1998, 1609-1617.
10. Page, M. I. The Mechanisms of Reactions of β-Lactam Antibiotics. Acc. Chem. Res. 1984, 17, 144-151. Page, M. I.; Laws, A. P. The Mechanism of Catalysis and The Inhibition of β-Lactamases. Chem. Commun. 1998, 1609-1617.
11. Reaction of a penicillin with hydrozine has been investigated before: Morris, J. J.; Page, M. I. Buffer Catalysis in the Hydrazinolysis of Benzylpenicillin. J. Chem. Soc., Perkin Trans. II 1980, 220-224.
12. +. J. Am. Chem. Soc. 1997, 119, 3403-3404. Gee, K. R.; Kueper, L. W.; Barnes, J.; Dudley, G.; Givens, R. S. Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters. J. Org. Chem. 1996, 61, 1228-1233. Holmes, C. P. Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. J. Org. Chem. 1997, 62, 2370-2380.
13. +. J. Am. Chem. Soc. 1997, 119, 3403-3404. Gee, K. R.; Kueper, L. W.; Barnes, J.; Dudley, G.; Givens, R. S. Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters. J. Org. Chem. 1996, 61, 1228-1233. Holmes, C. P. Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. J. Org. Chem. 1997, 62, 2370-2380.
14. +. J. Am. Chem. Soc. 1997, 119, 3403-3404. Gee, K. R.; Kueper, L. W.; Barnes, J.; Dudley, G.; Givens, R. S. Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters. J. Org. Chem. 1996, 61, 1228-1233. Holmes, C. P. Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. J. Org. Chem. 1997, 62, 2370-2380.
15. +. J. Am. Chem. Soc. 1997, 119, 3403-3404. Gee, K. R.; Kueper, L. W.; Barnes, J.; Dudley, G.; Givens, R. S. Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters. J. Org. Chem. 1996, 61, 1228-1233. Holmes, C. P. Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. J. Org. Chem. 1997, 62, 2370-2380.
16. +. J. Am. Chem. Soc. 1997, 119, 3403-3404. Gee, K. R.; Kueper, L. W.; Barnes, J.; Dudley, G.; Givens, R. S. Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters. J. Org. Chem. 1996, 61, 1228-1233. Holmes, C. P. Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. J. Org. Chem. 1997, 62, 2370-2380.
17. +. J. Am. Chem. Soc. 1997, 119, 3403-3404. Gee, K. R.; Kueper, L. W.; Barnes, J.; Dudley, G.; Givens, R. S. Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters. J. Org. Chem. 1996, 61, 1228-1233. Holmes, C. P. Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. J. Org. Chem. 1997, 62, 2370-2380.
18. (a) Evans, D. A.; Mathre, D. J.; Scott, W. L. Asymmetric Synthesis of the Enkephalinase Inhibitor Thiorphan. J. Org. Chem. 1985, 50, 1830-1835.
19. (b) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Stereoselective Amination of Chiral Enolates. A New Approach to the Asymmetric Synthesis of α-Hydrazino and α-Amino Acid Derivatives. J. Am. Chem. Soc. 1986, 108, 6395-6397.
20. Amit, B.; Zehavi, U.; Patchornik, A. Photosensitive Protecting Groups of Amino Sugars and Their Use in Glycoside Synthesis. 2-Nitrobenzyloxycarbonylamino and 6-Nitroveratryloxycarbonylamino Derivatives. J. Org. Chem. 1974, 39, 192-196.
21. 10-Dipeptidyl Cephalosporin Esters. J. Biol. Chem. 1986, 261, 7879-7887.
22. 10-Dipeptidyl Cephalosporin Esters. J. Biol. Chem. 1986, 261, 7879-7887.
23. 10-Dipeptidyl Cephalosporin Esters. J. Biol. Chem. 1986, 261, 7879-7887.
24. pUC19 β-Lactamase from Escherichia coli. J. Biol. Chem. 1999, 274, 23052.
25. pUC19 β-Lactamase from Escherichia coli. J. Biol. Chem. 1999, 274, 23052.
26. pUC19 β-Lactamase from Escherichia coli. J. Biol. Chem. 1999, 274, 23052.
27. Zafaralla, G.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Elucidation of the Role of Arginine-244 in the Turnover Process of Class A β-Lactamases. Biochemistry 1992, 31, 3847-3852.
28. Ross, G. W. Antibiotic Inactivation And Modification. β-Lactamase (Enterobacter Species). Methods Enzymol. 1975, 43, 678-687.
29. Micetich, R. G.; Sigh, R. A Convenient Synthesis of N-(1-Methoxyalkylidene) Derivatives of 6-Aminopenicillanic and 7-Aminocephalosporanic Acids. Synthesis 1985, 693-695.
30. Jones, R. N.; Barry, A. L.; Gavan, T. L.; Washington, J. A. In Manual of Clinical Microbiology, 4th ed.; Lennette, E. H., Balows, A., Hausler, W. J., Shadomy, H. J., Eds.; American Society for Microbiology: Washington, DC, 1985.