Probing the mechanism of action of potential anticancer agents at a molecular level using electrospray ionisation Fourier transform ion cyclotron resonance mass spectrometry

European Journal of Mass Spectrometry

Volumn 15, Issue 5, 2009, Pages 661-672

  Tietze, Lutz F ^a   Krewer, Birgit ^a   Frauendorf, Holm ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

ADEPT; Alkylating agent; Anti cancer drug; Covalent binding; DNA; DNA alkylation; Duocarmycin; ESI FT ICR mass spectrometry; Glutathione; RNA

Indexed keywords

ANTINEOPLASTIC AGENT; DNA; GLUTATHIONE; PRODRUG; RNA;

ALKYLATION; ARTICLE; CHEMISTRY; CYCLOTRON; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; METABOLISM; METHODOLOGY;

ALKYLATION; ANTINEOPLASTIC AGENTS; CYCLOTRONS; DNA; GLUTATHIONE; MASS SPECTROMETRY; PRODRUGS; RNA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 70349582549     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.1021     Document Type: Article

References (24)

1. 1. L.F. Tietze and B. Krewer, "Novel analogues of CC-1065 and the duocarmycins for the use in targeted tumour therapies", Anti-Cancer Agents in Med. Chem. 9, 304 I2009). doi: 10.2174/187152009787549205
2. 2. L.F. Tietze and T. Feuerstein, "Enzyme and proton- activated prodrugs for a selective cancer therapy", Curr. Pharm. Des. 9, 2155 (2003). doi: 10.1071/CH03036
3. K.D. Bagshawe. "Antibody directed enzymes revive anticancer prodrugs concept", Sr. J. Cancer 56, 531 (1987)
4. L.F. Tietze, F. Major, I. Schuberth, D.A. Spiegl, B. Krewer, K. Maksimenka, G. Bringmann and J. Magull, "Selective treatment of cancer: synthesis, biological evaluation and structural elucidation of novel analogues of the antibiotic CC-1065 and the duocarmycins", Chem. Eur. J. 13, 4396 (2007). doi: 10'.1002/chem. 200700113
5. L.F. Tietze, F. Major and I. Schuberth," Antitumor- wirkstoffe: Entwicklung hochpotenter glycosidi- scher Duocarmycin-Analoga fur eine setektive Krebstherapie", Angew. Chem. 118, 6724 (2006). doi: 10.1002/ange. 200600936;
6. L.F. Tietze, F. Major and I. Schuberth, "Antitumor agents: development of highly potent glycosidic duocarmycin analogues for selective cancer therapy", Angew. Chem., Int. Ed. 45, 6574 (2006). doi: 10.1002/anie.200600936
7. D.G. Martin, C. Biles, S.A. Gerpheide, L.J. Hanka, W.C. Krueger, J.P. McGovren, S.A. Mizsak, G.L. Neil, J.C. Stewart and J. Visser, "CC-1065 (NSC 298223), a potent new antitumor agent improved production and isolation, characterization and antitumor activity", J. Antibiot. 34, 1119(1981)
8. M. Ichimura, T. Ogawa, K. Takahashi, E. Kobayashi, I. Kawamoto, T. Yasuzawa, I. Takahashi and H. Nakano, "Duocarmycin, a new antitumor antibiotic from strepto- myces sp", J. Antibiot. 43, 1037 (1990)
9. M. Zientkowska, Evaluierung des Antibody Directed Enzyme Prodrug Therapy-Konzeptes im Mammakarzinom- und Lymphom-MausmodeU. Dissertation, Gottingen (2007)
10. D.L. Boger and S. Johnson, "CC-1065 und die Duocarmycine: Mechanistische Studien zum Verständnis ihrer biologischen Funktion", Angew. Chem. 108, 1542 (1996). doi: 10.1002/ange.19961081306;
11. D.L Boger and S. Johnson, "CC-1065 and the duocarmycins: understanding their biological function through mechanistic studies", Angew. Chem. Int. Ed. Engl. 35, 1438 (1996). doi: 10.1002/anie.199614381
12. L.H. Hurley and D.R. Needham-VanDevanter, "Covatent binding of antitumor antibiotics in the minor groove of DNA. Mechanism of action of CC-1065 and the pyr- rolo(1,4)benzodiazepines", Acc. Chem. Res. 19, 230 (1986). doi: 10.1021/ar00128a001
13. L.F. Tietze, B. Krewer, H. Frauendorf, F. Major and I. Schuberth, "Untersuchung der Reaktivitat und Selektivitat DNA-alkylierender Duocarmycin-Analoga mittels hochauflosender Massenspektrometrie", Angew. Chem. 118, 6720 (2006). doi: 10.1002/ange.200600935;
14. L.F. Tietze, B. Krewer, H. Frauendorf, F. Major and I. Schuberth, "Investigation of reactivity and selectivity of DNA-alkytating duocarmycin analogues by high-resolution mass spectrometry", Angew. Chem., Int. Ed. 45, 6570 (2006). doi: 10.1002/anie.200600935
15. S.A. Hofstadler, K.A. Sannes-Lowery and J.C. Hannis, "Analysis of Nucleic Acids by FTICR MS", Mass Spectrom. Rev. 24, 265 (2005). doi: 10.1002/mas.20016 (Pubitemid 40325549)
16. J.H. Banoub, R.P. Newton. E. Esmans, D.F. Ewing and 6. Mackenzie, "Recent developments in mass spectrometry for the characterization of nucleosides, nucleotides, oligonucleotides, and nucleic acids", Chem. Rev. 105, 1869 (2005). doi: 10.1021/cr030040w
17. M.L. Colgrave, P. lannitti-Tito, G. Wickham and M.M. Sheil, "Rapid determination of sequence selectivity and stability of alkylated oligonucleotide adducts by electrospray tandem mass spectrometry", Aust. J. Chem. 56, 401 (2003). doi: 10.1071/CH02205
18. J.L. Beck, M.L. Colgrave, S.F. Ralph and M.M. Sheil, "Electrospray ionization mass spectrometry of oligonucleotide complexes with drugs, metals, and proteins", Mass Spectrom. Rev. 20, 61 (2001). doi: 10.1002/mas.1003
19. J.P. Barry, P. Vouros, A.V. Schepdael and S.-J. Law, "Mass and sequence verification of modified oligonucleotides using electrospray tandem mass spectrometry", J. Mass Spectrom. 30, 993 (1995). doi: 10.1002/jms.1190300709
20. S.A. McLuckey and S. Habibi-Goudarzi, "Decompositions of multiply charged oligonucleotide anions", J. Am. Chem. Soc. 115, 12085 (1993). doi: 10.1021/ja00078a054
21. K. Alkhuder, K.L. Meibom, I. Dubail, M. Dupuis and A. Charbit, "Glutathione provides a source of cysteine essential for intracellular multiplication of Francisella tularensis", PLoS Pathog. 5, 1 (2009). doi: 10.1371/journal.ppat.1000284
22. D.M. Townsend and K.D. Tew, "The role of glutathione S-transferase in anti-cancer drug resistance", Oncogene 22, 7369 (2003). doi: 10.1038/sj.onc.1206940
23. A. Pompella, A. Visvikis, A. Paolicchi, V. de Tata and A.F. Casini, "The changing faces of glutathione, a cellular protagonist", Biochem. Pharmacol. 66, H99 (2003). doi: 10.1016/S0006-2952I03I00504-5
24. A. Pastore, G. Federici, E. Bestini and F. Piemonte, "Analysis of glutathione: implication in redox and detoxification", Clinica Chimica Acta 333, 19 (2003). doi: 10.1016/S0009-898K03100200-6.