Oxidative degradation studies of an oxazolidinone-derived antibacterial agent, RWJ416457, in aqueous solutions

References

• Breslin D, Sato Y, Karki SB. (2010). Mechanism of hydrolysis of a novel indolocarbazole topoisomerase I inhibitor. Eur J Pharm Sci, 39:291–297.
   PubMed Web of Science ®Google Scholar
• Karki SB, Treemaneekarn V, Ostovic D, Nerurkar M, Almarsson O. (2006). Design of an i.v. formulation of an unstable prodrug candidate for prostate cancer treatment: solution chemistry of N-(glutaryl-hyp-ala-ser-cyclohexylglycyl-gln-ser-leu)-doxorubicin. Drug Dev Ind Pharm, 32:327–334.
   PubMed Web of Science ®Google Scholar
• Shyam B., Karki D., Ostovic Ö., Almarsson M., Nerurkar V.. (2006). Treemaneekarn: Design of an IV Formulation of an Unstable Prodrug Candidate for Prostate Cancer Treatment: Solution Chemistry of N-(glutaryl-hyp-ala-ser-cyclohexylglycyl-gln-ser-leu)-doxorubicin and IV Formulation for the Treatment of Prostate Cancer. Drug Development and Industrial Pharmacy, 32:327.
   PubMed Web of Science ®Google Scholar
• Sato Y, Breslin D, Kitada H, Minagawa W, Nomoto T, Qin XZ et al. (2010). Parenteral formulation and thermal degradation pathways of a potent rebeccamycin based indolocarbazole topoisomerase I inhibitor. Int J Pharm, 390:128–133.
   PubMed Web of Science ®Google Scholar
• Hovorka S, Schöneich C. (2001). Oxidative degradation of pharmaceuticals: theory, mechanisms and inhibition. J Pharm Sci, 90:253–269.
   PubMed Web of Science ®Google Scholar
• Karki SB, Treemaneekarn V, Kaufman MJ. (2000). Oxidation of HMG-CoA reductase inhibitors by tert-butoxyl and 1, 1-diphenyl-2-picrylhydrazyl radicals: model reactions for predicting oxidatively sensitive compounds during preformulation. J Pharm Sci, 89:1518–1524.
   PubMed Web of Science ®Google Scholar
• Nelson ED, Harmon PA, Szymanik RC, Teresk MG, Li L, Seburg RA et al. (2006). Evaluation of solution oxygenation requirements for azonitrile-based oxidative forced degradation studies of pharmaceutical compounds. J Pharm Sci, 95:1527–1539.
   PubMed Web of Science ®Google Scholar
• Foleno BD, Abbanat D, Goldschmidt RM, Flamm RK, Paget SD, Webb GC et al. (2007). In vitro antibacterial activity of the pyrrolopyrazolyl-substituted oxazolidinone RWJ-416457. Antimicrob Agents Chemother, 51:361–365.
   PubMed Web of Science ®Google Scholar
• Livermore DM, Warner M, Mushtaq S, North S, Woodford N. (2007). In vitro activity of the oxazolidinone RWJ-416457 against linezolid-resistant and -susceptible staphylococci and enterococci. Antimicrob Agents Chemother, 51:1112–1114.
   PubMed Web of Science ®Google Scholar
• Vara Prasad JV. (2007). New oxazolidinones. Curr Opin Microbiol, 10:454–460.
   PubMed Web of Science ®Google Scholar
• Dinnocenzo JP, Karki SB, Jones JP. (1993). On isotope effects for the cytochrome P-450 oxidation of substituted N, N-dimethylanilines. J Am Chem Soc, 115:7111–7116.
   Web of Science ®Google Scholar
• Karki SB, Dinnocenzo JP. (1995). On the mechanism of amine oxidations by P450. Xenobiotica, 25:711–724.
   PubMed Web of Science ®Google Scholar
• Karki SB. (1995). Mechanism of oxidative amine dealkylation of cytochrome P-450. Diss Abstr Int B, 56:1426.
   Google Scholar
• Karki SB, Dinnocenzo JP, Jones JP, Korzekwa KR. (1995). Mechanism of oxidative amine dealkylation of substituted N, N-dimethylanilines by cytochrome P-450: application of isotope effect profiles. J Am Chem Soc, 117:3657–3664.
   Web of Science ®Google Scholar
• Mahapatra S, Halfen JA, Tolman WB. (1996). Mechanistic study of the oxidative N-dealkylation reactions of bis(í-oxo)dicopper complexes. J Am Chem Soc, 118:11575–11586.
   Web of Science ®Google Scholar
• Bietti M, Cuppoletti A, Dagostin C, Florea C, Galli C, Gentili P, et al. (1998). Stereoelectronic inhibition of deprotonation in the radical cation of N-benzylpiperidine: a contribution to the debate on the mechanism of N-dealkylation of tertiary amines. Eur J Org Chem, 11:2425–2429.
   Google Scholar
• Cocquet G, Ferroud C, Guy A. (2000). A mild and efficient procedure for ring-opening reactions of piperidine and pyrrolidine derivatives by single electron transfer photooxidation. Tetrahedron, 56:2975–2984.
   Web of Science ®Google Scholar
• Lewis F. (1986). Proton-transfer reactions of photogenerated radical ion pairs. Acc Chem Res, 19:401–405.
   Web of Science ®Google Scholar
• Maillard B, Ingold KU, Scaiano JC. (1983). Rate constants for the reactions of free radicals with oxygen in solution. J Am Chem Soc, 105:5095–5099.
   Web of Science ®Google Scholar
• Santamaria J, Raddachi MT, Rigaudy J. (1990). Electron-transfer activation. Photocyanation of tertiary amines. Tetrahedron Lett, 31:4735–4738.
   Web of Science ®Google Scholar
• Shearer J, Zhang CX, Hatcher LQ, Karlin KD. (2003). Distinguishing rate-limiting electron versus H-atom transfers in Cu2O2-mediated oxidative N-dealkylations: application of inter- versus intramolecular kinetic isotope effects. J Am Chem Soc, 125:12670–12671.
   PubMed Web of Science ®Google Scholar
• Gaudiano MC, Valvo L, Bertocchi P, Manna L. (2003). RP-HPLC study of the degradation of diclofenac and piroxicam in the presence of hydroxyl radicals. J Pharm Biomed Anal, 32:151–158.
   PubMed Web of Science ®Google Scholar
• MacFaul PA, Ingold KU, Lusztyk J. (1996). Kinetic solvent effects on hydrogen atom abstraction from phenol, aniline, and diphenylamine. The importance of hydrogen bonding on their radical-trapping (antioxidant) activities. J Org Chem, 61:1316–1321.
   Web of Science ®Google Scholar
• Valgimigli L, Banks JT, Ingold KU, Lusztyk J. (1995). Kinetic solvent effects on hydroxylic hydrogen atom abstractions are independent of the nature of the abstracting radical. Two extreme tests using vitamin E and phenol. J Am Chem Soc, 117:9966–9971.
   Web of Science ®Google Scholar