Photochemistry of oxazolidinone antibacterial drugs

Photochemistry and Photobiology

Volumn 85, Issue 4, 2009, Pages 879-885

  Fasani, Elisa ^a   Tilocca, Fedele ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY;

ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; OXAZOLIDINONES; PHOTOCHEMISTRY; SPECTROPHOTOMETRY, INFRARED;

EID: 67650941712     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2009.00546.x     Document Type: Article

References (38)

1. Barbachyn, M. R. C. W. Ford (2003) Oxazolidinone structure-activity relationships leading to linezolid. Angew. Chem. Int. Ed. Engl. 42, 2010 2023. (Pubitemid 36604340)
2. Barrett, J. F. (2000) Linezolid Pharmacia Corp. Curr. Opin. Investig. Drugs 1 (2 181 187. (Pubitemid 30811018)
3. Slee, A. M., M. A. Wuonola, R. J. McRipley, I. Zajac, M. J. Zawada, P. T. Bartholomew, W. A. Gregory M. Forbes (1987) Oxazolidinones, a new class of synthetic antibacterial agents: In vitro and in vivo activities of DuP 105 and DuP 721. Antimicrob. Agents Chemother. 31 (11 1791 1797. (Pubitemid 17157646)
4. Barbachyn, M. R., S. J. Brickner, G. J. Cleek, R. C. Gadwood, K. C. Grega, S. K. Hendges, D. K. Hutchinson, P. R. Manninen K. Munesada (1997) Design and synthesis of novel oxazolidinones active against multidrug-resistant bacteria. Spec. Publ. - RSC 198, 15 26.
5. Brickner, S. J., D. K. Hutchinson, M. R. Barbachyn, P. R. Manninen, D. A. Ulanowicz, S. A. Garmon, K. C. Grega, S. K. Hendges, D. S. Toops, C. W. Ford G. E. Zurenko (1996) Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections. J. Med. Chem. 39 (3 673 679.
6. Burkhardt, O., M. W. Pletz, C. P. Mertgen T. Welte (2007) Linezolid - The first oxazolidinone in the treatment of nosocomial MRSA pneumonia. Recent Patents Anti-Infect. Drug Disc. 2 (2 123 130. (Pubitemid 46952435)
7. Von Der Lippea, B., P. Sandvenb O. Brubakk (2006) Efficacy and safety of linezolid in multidrug resistant tuberculosis (MDR-TB) - A report of ten cases. J. Infect. 52 (2 92 96. (Pubitemid 43137390)
8. Grau, S. C. Rubio-Terrés (2008) Pharmacoeconomics of linezolid. Expert Opin. Pharmacother. 9 (6 987 1000. (Pubitemid 351605798)
9. Johnson, A. P. (2003) The future prospects of oxazolidinones. Investing. Drugs J. 6 (3 240 245. (Pubitemid 36717190)
10. Hutchinson, D. K. (2003) Oxazolidinone antibacterial agents: A critical review. Curr. Top. Med. Chem. 3 (9 1021 1042.
11. Bernard, L., R. Stern, D. Lew P. Hoffmeyer (2003) Serotonin syndrome after concomitant treatment with linezolid and citalopram. Clin. Infect. Dis. 36 (9 1197. (Pubitemid 36549644)
12. Freccero, M., M. Fagnoni A. Albini (2003) Homolytic vs heterolytic paths in the photochemistry of haloanilines. J. Am. Chem. Soc. 125 (43 13182 13190. (Pubitemid 37305616)
13. Monti, S., S. Sortino, E. Fasani A. Albini (2001) Multifaceted photoreactivity of 6-fluoro-7-aminoquinolones from the lowest excited states in aqueous media: A study by nanosecond and picosecond spectroscopic techniques. Chem. Eur. J. 7, 2185 2196. (Pubitemid 32506004)
14. Albini, A. S. Monti (2003) Photophysics and photochemistry of fluoroquinolones. Chem. Soc. Rev. 32 (4 238 250. (Pubitemid 38333553)
15. Marrot, L., J. Belaïdi, C. Jones, P. Perez L. Riou (2003) Molecular responses to photogenotoxic stress induced by the antibiotic lomefloxacin in human skin cells: From DNA damage to apoptosis. J. Invest. Dermatol. 121, 596 606. (Pubitemid 37072274)
16. Martin, G. E., R. H. Robins, P. B. Bowman, W. K. Duholke, K. A. Farley, B. D. Kaluzny, J. E. Guido, S. M. Sims, T. J. Thamann, B. J. Thompson, T. Nishimura, Y. Noro T. Tahara (1999) Susceptibility of morpholine substituents to photo-oxidative decomposition - Identification of photo-oxidative degradants of linezolid. J. Heteroc. Chem. 36 (1 265 270. (Pubitemid 29161900)
17. Agrawal, H., K. R. Mahadik N. Paradkar (2003) Stability indicating HPTLC determination of linezolid as bulk drug and in pharmaceutical dosage form. Drug Dev. Ind. Pharm. 29 (10 1119 1126. (Pubitemid 37499547)
18. Rao, B. M., M. K. Srinivasu, G. Sridhar, P. R. Kumar, K. B. Chandrasekhar A. Islam (2005) A stability indicating LC method for zolmitriptan. J. Pharm. Biomed. Anal. 39, 503 509. (Pubitemid 41196055)
19. Fasani, E., F. Tilocca, S. Protti, D. Merli A. Albini (2008) Photoionization and photoheterolytic defluorination in the drug linezolid and related molecules. SN1(Ar*) vs. SR+N1(Ar*) mechanism. Org. Biomol. Chem. 6, 4634 4642.
20. Renslo, A. R., P. Jaishankar, R. Venkatachalam, C. Hackbarth, S. Lopez, D. V. Patel M. F. Gordeev (2005) Conformational constraint in oxazolidinone antibacterials. Synthesis and structure-activity studies of (azabicyclo[3.1.0] hexylphenyl)oxazolidinones. J. Med. Chem. 48 (15 5009 5024. (Pubitemid 41033141)
21. Selvakumar, N., B. Yadi Reddy, G. Sunil Kumar, M. K. Khera, D. Srinivas, M. Sitaram Kumar, J. Das, J. Iqbal S. Trehan (2006) Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of linezolid. Bioorg. Med. Chem. Lett. 16 (16 4416 4419.
22. Srivastava, B. K., M. R. Jain, M. Solanki, R. Soni, D. Valani, S. Gupta, B. Mishra, V. Takale, P. Kapadnis, H. Patel, P. Pandya, J. Z. Patel P. R. Patel (2008) Synthesis and in vitro antibacterial activities of novel oxazolidinones. Eur. J. Med. Chem. 43 (4 683 693.
23. Vara Prasad, J. V. (2007) New oxazolidinones. Curr. Opin. Microbiol. 10 (5 454 460.
24. Komine, T., A. Kojima, Y. Asahina, T. Saito, H. Takano, T. Shibue Y. Fukuda (2008) Synthesis and structure-activity relationship studies of highly potent novel oxazolidinone antibacterials. J. Med. Chem. 51 (20 6558 6562.
25. Selvakumar, N., G. G. Rajulu, K. C. Reddy, B. C. Chary, P. K. Kumar, T. Madhavi, K. Praveena, K. H. Reddy, M. Takhi, A. Mallick, P. V. Amarnath, S. Kandepu J. Iqbal (2008) Synthesis, SAR, and antibacterial activity of novel oxazolidinone analogues possessing urea functionality. Bioorg. Med. Chem. Lett. 18 (2 856 860.
26. Selvakumar, N., D. Srinivas, M. K. Khera, M. S. Kumar, R. N. Mamidi, H. Sarnaik, C. Charavaryamath, B. S. Rao, M. A. Raheem, J. Das, J. Iqbal R. Rajagopalan (2002) Synthesis of conformationally constrained analogues of linezolid: Structure-activity relationship (SAR) studies on selected novel tricyclic oxazolidinones. J. Med. Chem. 45 (18 3953 3962. (Pubitemid 35024297)
27. Tokuyama, R., Y. Takahashi, Y. Tomita, M. Tsubouchi, N. Iwasaki, N. Kado, E. Okezaki O. Nagata (2001) Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 3. Synthesis and evaluation of 5-thiocarbamate oxazolidinones. Chem. Pharm. Bull. 49 (4 361 367. (Pubitemid 32367664)
28. Tokuyama, R., Y. Takahashi, Y. Tomita, M. Tsubouchi, T. Yoshida, N. Iwasaki, N. Kado, E. Okezaki O. Nagata (2001) Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 2. Relationship between lipophilicity and antibacterial activity in 5-thiocarbonyl oxazolidinones. Chem. Pharm. Bull. 49 (4 353 360. (Pubitemid 32367663)
29. Hatchard, C. G. C. A. Parker (1956) A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer. Proc. R. Soc. London, Ser. A 235, 518 536.
30. Dawson, W. R. M. W. Windsor (1968) Fluorescence yields of aromatic compounds. J. Phys. Chem. 72 (9 3251 3260.
31. Barbachyn, M. R., G. J. Cleek, L. A. Dolak, S. A. Garmon, J. Morris, E. P. Seest, R. C. Thomas, D. S. Toops, W. Watt, D. G. Wishka, C. W. Ford, G. E. Zurenko, J. C. Hamel, R. D. Schaadt, D. Stapert, B. H. Yagi, W. J. Adams, J. M. Friis, J. G. Slatter, J. P. Sams, N. L. Oien, M. J. Zaya, L. C. Wienkers M. A. Wynalda (2003) Identification of phenylisoxazolines as novel and viable antibacterial agents active against Gram-positive pathogens. J. Med. Chem. 46 (2 284 302. (Pubitemid 36078146)
32. Schultze, H. (1973) Photolysis of N-substituted O-alkylurethanes. Z. Naturforsch. (B) 28 (5-6 339 352.
33. Lewis, F. D. W. Liu (1999) Luminescence of N-arylbenzamides in low-temperature glasses. J. Phys. Chem. A 103 (48 9678 9686. (Pubitemid 129583203)
34. Othmen, K., P. Boule, B. Szczepanik, K. Rotkiewicz G. Grabner (2000) Photochemistry of 4-chloroaniline in solution. Formation and kinetic properties of a new carbene, 4-iminocyclohexa-2,5-dienylidene. J. Phys. Chem. A 104 (42 9525 9534. (Pubitemid 30966706)
35. Guizzardi, B., M. Mella, M. Fagnoni, M. Freccero A. Albini (2001) Generation and reactivity of the 4-aminophenyl cation by photolysis of 4-chloroaniline. J. Org. Chem. 66 (19 6353 6363. (Pubitemid 32868369)
36. Lazzaroni, S., D. Dondi, M. Fagnoni A. Albini (2008) Geometry and energy of substituted phenyl cations. J. Org. Chem. 73 (1 206 211.
37. Fasani, E., F. F. Barberis Negra, M. Mella, S. Monti A. Albini (1999) Photoinduced C-F bond cleavage in some fluorinated 7-amino-4-quinolone-3- carboxylic acids. J. Org. Chem. 64 (15 5388 5395.
38. Martinez, L. C. F. Chignell (1998) Photocleavage of DNA by the fluoroquinolone antibacterials. J. Photochem. Photobiol. B, Biol. 45, 51 59. (Pubitemid 28491048)