Cancer Letters
Volume 262, Issue 1 , Pages 123-132 , 8 April 2008

Monitoring incorporation, transformation and subcellular distribution of N-l-leucyl-doxorubicin in uterine sarcoma cells using capillary electrophoretic techniques

Received 6 August 2007 ,Revised 27 November 2007 ,Accepted 27 November 2007.

References 

  1. Blum RH, Carter SK. Adriamycin. A new anticancer drug with significant clinical activity. Ann. Intern. Med. 1974;80:249–259
  2. Young RC, Ozols RF, Myers CE. The anthracycline antineoplastic drugs. New Engl. J. Med. 1981;305:139–153
  3. Trouet A, Deprez-De Campeenre D, Baurain R, Masquelier M. N-l-leucyl derivatives of daunorubicin and doxorubicin as new prodrugs of anthracyclines. In:  Mathé G,  Maral R,  De Jager R editor. Anthracyclines: current status and future developments. New York: Masson Pub. USA; 1983;p. 179–181
  4. Masquelier M, Baurain R, Trouet A. Amino acid and dipeptide derivatives of daunorubicin. 1. Synthesis, physicochemical properties, and lysosomal digestion. J. Med. Chem. 1980;23:1166–1170
  5. Zbinden G, DeCampeenere D, Baurain R. Preclinical assessment of the cardiotoxic potential of anthracycline antibiotics: N-l-leucyl-doxorubicin. Arch. Toxicol. Suppl. 1991;14:107–117
  6. Breistol K, Hendriks HR, Berger DP, Langdon SP, Fiebig HH, Fodstad O. The antitumour activity of the prodrug N-l-leucyl-doxorubicin and its parent compound doxorubicin in human tumour xenografts. Eur. J. Cancer. 1998;34:1602–1606
  7. Breistol K, Hendriks HR, Fodstad O. Superior therapeutic efficacy of N-l-leucyl-doxorubicin versus doxorubicin in human melanoma xenografts correlates with higher tumour concentrations of free drug. Eur. J. Cancer. 1999;35:1143–1149
  8. de Jong J, Geijssen GJ, Munniksma CN, Vermorken JB, van der Vijgh WJF. Plasma pharmacokinetics and pharmacodynamics of a new prodrug N-l-leucyl-doxorubicin and its metabolites in a phase I clinical trial. J. Clin. Oncol. 1992;10:1897–1906
  9. de Jong J, Vermorken JB, Van der Vijgh WJF. Analysis and pharmacokinetics of a new prodrug N-l-leucyldoxorubicin and its metabolites in plasma using HPLC with fluorescence detection. J. Pharm. Biomed. Anal. 1992;10:309–314
  10. de Jong J, Klein I, Bast A, van der Vijgh WJF. Analysis and pharmacokinetics of N-l-leucyldoxorubucin and metabolites in tissues of tumor-bearing BALB/c mice. Cancer Chemother. Pharmacol. 1992;31:156–160
  11. Wilstermann AM, Osheroff N. Stabilization of eukaryotic topoisomerase II-DNA cleavage complexes. Curr. Top. Med. Chem. 2003;3:321–338
  12. Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem. Pharmacol. 1999;57:727–741
  13. Reinhoud NJ, Tjaden UR, Irth H, van der Greef J. Bioanalysis of some anthracyclines in human plasma by capillary electrophoresis with laser-induced fluorescence detection. J. Chromatogr. 1992;574:327–334
  14. Simeon N, Chatelut E, Canal P, Nertz M, Couderc F. Anthracycline analysis by capillary electrophoresis. Application to the analysis of daunorubicine in Kaposi sarcoma tumor. J. Chromatogr. A. 1999;853:449–454
  15. Anderson AB, Ciriacks CM, Fuller KM, Arriaga EA. Distribution of zeptomole-abundant doxorubicin metabolites in subcellular fractions by capillary electrophoresis with laser-induced fluorescence detection. Anal. Chem. 2003;75:8–15
  16. Anderson AB, Gergen J, Arriaga EA. Detection of doxorubicin and metabolites in cell extracts and in single cells by capillary electrophoresis with laser-induced fluorescence detection. J. Chromatogr. B. 2002;769:97–106
  17. Gosland MP, Lum BL, Sikic BI. Reversal by cefoperazone of resistance to etoposide, doxorubicin, and vinblastine in multidrug resistant human sarcoma cells. Cancer Res. 1989;49:6901–6905
  18. Chen G, Duran GE, Steger KA, Lacayo NJ, Jaffrezou JP, Dumontet C, et al. Multidrug-resistant human sarcoma cells with a mutant P-glycoprotein, altered phenotype, and resistance to cyclosporins. J. Biol. Chem. 1997;272:5974–5982
  19. Lau DH, Duran GE, Lewis AD, Sikic BI. Metabolic conversion of methoxymorpholinyl doxorubicin: from a DNA strand breaker to a DNA cross-linker. Br. J. Cancer. 1994;70:79–84
  20. Battisti RF, Zhong Y, Fang L, Gibbs S, Shen J, Nadas J, et al. Modifying the sugar moieties of daunorubicin overcomes P-gp-mediated multidrug resistance. Mol. Pharm. 2007;4:140–153
  21. Stelakatos GC, Theodoropoulos DM, Zervas L. On the trityl method for peptide synthesis. J. Am. Chem. Soc. 1959;81:2884–2887
  22. Anderson GW, Zimmerman JE, Callahan FM. The use of easter of N-hydroxysuccinimide in peptide synthesis. J. Am. Chem. Soc. 1964;86:1839–1842
  23. Sobottka SB, Berger MR. Assessment of antineoplastic agents by MTT assay – partial underestimation of antiproliferative properties. Cancer Chemother. Pharmacol. 1992;30:385–393
  24. Graham JM, Rickwood D. Subcellular fractionation: a practical approach. Oxford: IRL Press at Oxford University Press; 1997;
  25. Duffy CF, Gafoor S, Richards DP, Admadzadeh H, O’Kennedy R, Arriaga EA. Determination of properties of individual liposomes by capillary electrophoresis with postcolumn laser-induced fluorescence detection. Anal. Chem. 2001;73:1855–1861
  26. Eder AR, Chen JS, Arriaga EA. Separation of doxorubicin and doxorubicinol by cyclodextrin-modified micellar electrokinetic capillary chromatography. Electrophoresis. 2006;27:3263–3270
  27. Dalmark M, Storm HH. A Fickian diffusion transport process with features of transport catalysis. Doxorubicin transport in human red blood cells. J. Gen. Physiol. 1981;78:349–364
  28. Harker WG, Sikic BI. Multidrug (pleiotropic) resistance in doxorubicin-selected variants of the human sarcoma cell line MES-SA. Cancer Res. 1985;45:4091–4096
  29. Eder AR, Arriaga EA. Micellar electrokinetic capillary chromatography reveals differences in intracellular metabolism between liposomal and free doxorubicin treatment of human leukemia cells. J. Chromatogr. B. 2005;829:115–122
  30. Li XF, Ren H, Le X, Qi M, Ireland ID, Dovichi NJ. Migration time correction for the analysis of derivatized amino acids and oligosaccharides by micellar capillary electrochromatography. J. Chromatogr A. 2000;869:375–384
  31. Bennis S, Garcia C, Robert J. Aspects of the cellular pharmacology of N-l-leucyldoxorubicin in human tumor cell lines. Biochem. Pharmacol. 1993;45:1929–1931
  32. Schindler M, Grabski S, Hoff E, Simon SM. Defective pH regulation of acidic compartments in human breast cancer cells (MCF-7) is normalized in adriamycin-resistant cells (MCF-7adr). Biochemistry. 1996;35:2811–2817
  33. Zijlstra JG, de Vries EG, Mulder NH. Multifactorial drug resistance in an adriamycin-resistant human small cell lung carcinoma cell line. Cancer Res. 1987;47:1780–1784

PII: S0304-3835(07)00589-7

doi: 10.1016/j.canlet.2007.11.034

Cancer Letters
Volume 262, Issue 1 , Pages 123-132 , 8 April 2008

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