In vitro cytotoxicity study of oxaziridines generated after chlordiazepoxide, demoxepam, and desmethylchlordiazepoxide UV irradiation

References

• Abikhalil, F., Dubois, J., Hanocq, M., Atassi, G. (1986). A new algorithm for computing the parameters of linear compartment models in pharmacokinetics. Eur J Drug Metab. Pharmacokinet 11: 51–59.
   PubMed Web of Science ®Google Scholar
• Arnould, R., Dubois, J., Abikhalil, F., Libert, A., Ghanem, G., Atassi, G., et al. (1990). Comparison of two cytotoxicity assays—tetrazolium derivative reduction (MTT) and tritiated thymidine uptake—on three malignant mouse cell lines using chemotherapeutic agents and investigational drugs. Anticancer Res 10: 145–154.
   PubMed Web of Science ®Google Scholar
• Azquetta, A., Arbillaga, L., Pachon, G., Cascante, M., Creppy, E.E., Lopez de Cerain, A. (2007). A quinoxaline 1,4-di-N-oxide derivative induces DNA oxidative damage not attenuated by vitamin C and E treatment. Chemico Biolog Interact 168: 95–105.
   PubMed Web of Science ®Google Scholar
• Bakri, A.G., Beijersbergen van Henegouwen M.J., Chanal, J.L. (1983). Photopharmacology of the tranquilizer, chlordiazepoxide, in relation to its phototoxicity. Photochem Photobiol 38: 177–183.
   PubMed Web of Science ®Google Scholar
• Bakri, A., Beijersbergen van Henegouwen G., Chanal, J.L. (1985). Involvement of the N4-oxide group in the phototoxicity of chlordiazepoxide in the rat. Photodermatology 2: 205–212.
   PubMedGoogle Scholar
• Bakri, A., Beijersbergen van Henegouwen G.M.J., De Vries, H. (1988). Photobinding of some 7-chloro-1,4-benzodiazepines to human plasma protein in vitro and photopharmacology of diazepam in the rat. Pharm Weekbl Sci 10: 122–129.
   PubMedGoogle Scholar
• Bakri, A., Beijersbergen van Henegouwen G.M.J., Sedee, A.G.J. (1986). Irreversible binding of chlordiazepoxide to human plasma protein induced by UV-A radiation. Photochem Photobiol 44: 181–185.
   PubMed Web of Science ®Google Scholar
• Beijersbergen van Henegouwen G.M.J., Cornelissen, P.J.G., Bakri, A., De Vries, H. (1985). Photoreactions of xenobiotics in the skin resulting in systemic effects (e.g., chlordiazepoxide). NATO ASI Ser A Life Sci 38: 177–183.
   Google Scholar
• Beijersbergen van Henegouwen G.M.J.. (1991). (Systemic) phototoxicity of drugs and other xenobiotics. J Photochem Photobiol B 10: 183–210.
   PubMed Web of Science ®Google Scholar
• Bell, S.C., Sulkowski, T.S., Gochman, C., Childress, S.J. 1962. 1,3-dihydro-2H-1,4-benzodiazepine-2-ones and their 4-oxides. J. Org. Chem. 27:562–566.
   Web of Science ®Google Scholar
• Bourin, M. (1981). Benzodiazepines. Pharmacocinetic basis of benzodiazepines pescription. Paris, France: Ellipses.
   Google Scholar
• Cornelissen, P.J.G., Beijersbergen van Henegouwen, G.M.J., Gerritsma, K.W. (1979). Photochemical decomposition of 1,4-benzodiazepines. Chlordiazepoxide. Int J Pharm 3:205–220.
   Google Scholar
• Cornelissen, P.J.G., Beijersbergen van Henegouwen G.M.J., Mohn, G.R. (1980). Structure and photobiological activity of 7-chloro-1,4-benzodiazepines. Studies on the phototoxic effects of chlordiazepoxide, desmethylchlordiazepoxide, and demoxepam using a bacterial indicator system. Photochem Photobiol 32:653–659.
   PubMed Web of Science ®Google Scholar
• Dubois, J., Abi Khalil, F., Hanocq, M., Atassi, G., Arnould, R. (1989). Adjustment of the dose-effect curve by means of an original algorithm. Application to the study of cytotoxicity in vitro. J Pharm Belg 44:181–191.
   PubMedGoogle Scholar
• Holford, N.H.G., Sheiner, L.B. (1986). Kinetics of pharmacologic response. In: Rowland, Tucker (Eds.), Pharmacokinetics: Theory and Methodology (pp 194–197) Oxford, UK: Pergamon Press.
   Google Scholar
• Kessel, D., Antolovich, M., Smith, K.M. (2001). The role of the peripheral benzodiazepine receptor in the apoptotic response to photodynamic therapy. Photochem Photobiol 74:346–349.
   PubMed Web of Science ®Google Scholar
• Matthew, E., Laskin, J.D., Zimmerman, E.A., Weinstein, I.B., Hsu, K.C., Engelhardt, D.L. (1981). Benzodiazepines have high-affinity binding sites and induce melanogenesis in B16/C3 melanoma cells. Proc Natl Acad Sci U S A 78:3935–3939.
   PubMed Web of Science ®Google Scholar
• Patterson, L.H. (2002). Bioreductively activated antitumor N-oxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy. Drug Metab Rev 34:581–592.
   PubMed Web of Science ®Google Scholar
• Physicians’ Desk Reference (PDR). (2006). Physician’s Desk Reference, 2006. Montvale, New Jersey, USA: Thomson PDR.
   Google Scholar
• Soentjens-Werts, V., Dubois, J.G., Atassi, G., Hanocq, M. (1994). High-performance liquid chromatographic determination of chlordiazepoxide, its metabolites, and oxaziridines generated after UV irradiation. J Chromatogr A 662:255–262.
   Web of Science ®Google Scholar
• Soentjens-Werts, V., Dubois, J. G., Atassi, G., Hanocq, M. (1995). Chlordiazepoxide photoisomerization kinetics into oxaziridine. A HPLC study. Talanta 42:581–589.
   PubMed Web of Science ®Google Scholar
• Sternbach, L.H., Reeder, E. (1961). Quinazolines and 1,4-benzodiazepines. II. The rearrangement of 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide into 2-amino derivatives of 7-chloro-5-phenyl-3H-1,4-benzodiazepine 4-oxide. J Org Chem 26:1111–1118.
   Web of Science ®Google Scholar
• Weng, Q., Duoduo, W., Peng, G., Liang, F., Yongzhou, H., Qiaojun, H., et al. (2008). Q39, a novel synthetic quinoxaline 1,4-di-N-oxide compound with anticancer activity in hypoxia. Eur J Pharmacol 581:262–269
   PubMed Web of Science ®Google Scholar
• Yin, H., Xu, Y., Qian, X., Li, Y., Liu, J. (2007). Novel N-oxide of naphthalimides as prodrug leads against hypoxic solid tumor: synthesis and biological evaluation. Bioorg Med Chem Lett 17:2166–2170.
   PubMed Web of Science ®Google Scholar