Reactions of 4-[bis(2-chloroethyl)amino]benzenebutanoic acid (chlorambucil) with DNA

Chemistry and Biodiversity

Volumn 6, Issue 7, 2009, Pages 1002-1013

  Florea Wang, Diana ^a   Pawlowicz, Agnieszka J ^b   Sinkkonen, Jari ^a   Kronberg, Leif ^b   Vilpo, Juhani ^c   Hovinen, Jari ^a,d  

^a UNIVERSITY OF TURKU   (Finland)

^b ÅBO AKADEMI UNIVERSITY   (Finland)

^c TAMPERE UNIVERSITY HOSPITAL   (Finland)

^d PerkinElmer   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 7 (2 {[4 (3 CARBOXYPROPYL)PHENYL](2 HYDROXY ETHYL)AMINO}ETHYL) 9 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 6 OXO 6,9 DIHYDRO 1H PURIN 7 IUM; 2 AMINO 7,9 BIS(2 {[4 (3 CARBOXYPROPYL)PHENYL](2 HYDROXYETHYL)AMINO} ETHYL) 6 OXO 6,7 DIHYDRO 1H PURIN 9 IUM; 4 (4 {[2 (2 AMINO 6 OXO 1H PURIN 7(6H) YL)ETHYL](2 HYDROXYETHYL)AMINO} PHENYL)BUTANOIC ACID; 4 (4 {[2 (6 AMINO 3H PURIN 3 YL)ETHYL](2 HYDROXYETHYL)AMINO} PHENYL)BUTANOIC ACID; 4 (4 {[2 ({1 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 4 IMINO 1,4 DIHYDROPYRIMIDIN 2 YL}OXY)ETHYL] (2 HYDROXYETHYL)AMINO}PHENYL)BUTANOIC ACID; 4 (4 {[2 ({9 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 9H PURIN 6 YL}AMINO)ETHYL](2 HYDROXYETHYL) AMINO}PHENYL)BUTANOIC ACID; 4 (4 {BIS[2 (2 AMINO 6 OXO 1H PURIN 7(6H) YL)ETHYL] AMINO}PHENYL)BUTANOIC ACID; 4 [4 ({2 [(2,3,5) 5 (2 AMINO 6 OXO 1H PURIN 9(6H) YL) 2 (HYDROXYMETHYL)TETRAHYDROFURAN 3 YLOXY]ETHYL}(2 HYDROXY ETHYL)AMINO)PHENYL]BUTANOIC ACID; 4 {4 [(2 HYDROXYETHYL)(2 {[(2,3,5) 2 (HYDROXYMETHYL) 5 (5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL)TETRAHYDROFURAN 3 YL]OXY}ETHYL)AMINO]PHENYL} BUTANOIC ACID; 4 {4 [(2 {3 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 2,6 DIOXO 2,3 DIHYDROPYRIMIDIN 1(6H) YL}ETHYL) (2 HYDROXYETHYL)AMINO]PHENYL} BUTANOIC ACID; 4 {4 [(2 {3 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 5 METHYL 2,6 DIOXO 2,3 DIHYDROPYRIMIDIN 1(6H) YL} ETHYL)(2 HYDROXYETHYL)AMINO]PHENYL}BUTANOIC ACID; 4 {4 [(2 {3 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 6 IMINO 2 OXO 2,3 DIHYDROPYRIMIDIN 1(6H) YL}ETHYL) (2 HYDROXYETHYL)AMINO]PHENYL} BUTANOIC ACID; 4 {4 [(2 {9 [(2,4,5) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 6 IMINO 6,9 DIHYDRO 1H PURIN 1 YL}ETHYL) (2 HYDROXYETHYL)AMINO]PHENYL}BUTANOIC ACID; 4 {4 [(2 {[(2,3,5) 5 (4 AMINO 2 OXOPYRIMIDIN 1(2H) YL) 2 (HYDROXYMETHYL)TETRAHYDROFURAN 3 YL]OXY}ETHYL)(2 HYDROXYETHYL) AMINO]PHENYL}BUTANOIC ACID; 4 {4 [(2{[(2,3,5) 5 (6 AMINO 9H PURIN 9 YL) 2 2 (HYDROXYMETHYL)TETRAHYDROFURAN 3 YL]OXY}ETHYL)(2 HYDROXYETHYL)AMINO] PHENYL}BUTANOIC ACID; CHLORAMBUCIL; DOUBLE STRANDED DNA; HYDROLASE; NUCLEOSIDE DERIVATIVE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; CYTOTOXICITY; DNA ADDUCT; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MUTAGENIC ACTIVITY; NUCLEAR MAGNETIC RESONANCE; PH; ROOM TEMPERATURE; SPIKE; TANDEM MASS SPECTROMETRY; ULTRAVIOLET RADIATION;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; CATTLE; CHLORAMBUCIL; CHROMATOGRAPHY, LIQUID; DNA; DNA ADDUCTS; DNA, SINGLE-STRANDED; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 67749120571     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200800327     Document Type: Article

References (40)

1. C. B. Faguet, J. Clin. Oncol. 1994, 12, 1974.
2. C. R. Willis, A. Goodrich, K. Park, J. K. Waselenko, M. Lucas, A. Reese, L. F. Diehl, M. R. Grever, J. C. Byrd, I. W. Flinn, Ann. Hematol. 2006, 85, 301.
3. S. Wöhrer, M. Raderer, H. Kaufmann, M. Hejna, A. Chott, C. Zelinski, J. Drach, Onkologie 2005, 28, 73.
4. R. A. Kyle, P. R. Greipp, M. A. Gertz, T. E. Witzig, J. A. Lust, M. Q. Lacy, T. M. Therneau, Br. J. Haematol. 2000, 108, 737.
5. L. A. Hansen, B. D. Clayton, Drug Intell. Clin. Pharm. 1984, 18, 569.
6. N. I. Berlin, L. R. Wasserman, J. Lab. Clin. Med. 1997, 130, 365.
7. K. S. McCully, G. V. Narayansingh, G. P. Cumming, T. K. Sarkar, D. E. Parkin, Scot. Med. J. 2000, 45, 51.
8. M. Polenakovic, L. Grcevska, S. Dzikova, Macedon. Acad. Sci. Arts, Sect. Biol. Med. Sci. 2006, 27(2), 5.
9. B. Singer, J. T. Kusmierek, Annu. Rev. Biochem. 1982, 52, 655.
10. M. J. Lind, C. Ardiet, Cancer Surveys 1993, 17, 157.
11. J. E. F. Reynolds, 'Martindale The Extra Pharmacopoeia', 31st edn., Royal Pharmaceutical Society, London, 1996, p. 550.
12. E. Haapala, K. Hakala, E. Jokipelto, J. Vilpo, J. Hovinen, Chem. Res. Toxicol. 2001, 14, 988.
13. D. Florea-Wang, E. Haapala, J. Mattinen, K. Hakala, J. Vilpo, J. Hovinen, Chem. Res. Toxicol. 2003, 16, 403.
14. D. Florea-Wang, E. Haapala, J. Mattinen, K. Hakala, J. Vilpo, J. Hovinen, Chem. Res. Toxicol. 2004, 17, 383.
15. J. Hovinen, A. Guzaev, A. Azhayev, H. Lönnberg, J. Chem. Soc., Perkin Trans. 1 1994, 2745.
16. L. F. Povirk, D. E. Shuker, Mutat. Res. 1994, 318, 205.
17. P. O. Pieper, B. W. Futscher, L. C. Erickson, Carcinogenesis 1989, 10, 1307.
18. P. O. Pieper, L. C. Erickson, Carcinogenesis 1990, 11, 1739.
19. B. B. Bank, Biochem. Pharmacol. 1992, 44, 571.
20. W. B. Mattes, C. -S. Lee, J. Laval, T. R. O'Connor, Carcinogenesis 1996, 17, 643.
21. P. Wang, G. W. Bauer, R. A. Bennett, L. F. Povirk, Biochemistry 1991, 30, 11515.
22. G. B. P. Bauer, P. Wang, G. E. Kellogg, D. J. Abraham, L. F. Povirk, Proc. Am. Assoc. Cancer Res. 1993, 34, 136; cited in ref. 16.
23. M. I. Jesson, J. B. Johnston, E. Robotham, A. Begleiter, Cancer Res. 1989, 49, 7031.
24. Q. Zhang, E. Yu, K. A. Kellersberger, E. Crosland, D. Fabris, J. Am. Soc. Mass Spectrom. 2006, 17, 1570.
25. T. Itaya, T. Harada, J. Chem. Soc., Chem. Commun. 1984, 858.
26. T. Lindahl, Nature 1993, 362, 709.
27. M. H. Benn, P. Kazmaier, C. Watanatada, L. N. Owen, J. Chem. Soc. D, Chem. Commun. 1970, 1685.
28. W. R. Owen, P. J. Stewart, J. Pharm. Sci. 1979, 68, 992.
29. P. M. Cullins, R. E. Green, M. E. Malone, J. Chem. Soc. Perkin Trans. 2 1995, 1503.
30. T. Pettersson-Fernholm, J. Vilpo, M. Kosonen, K. Hakala, J. Hovinen, J. Chem. Soc., Perkin Trans. 2 1999, 2183.
31. 'Goodman & Gilman's The Pharmacological Basis of Therapeutics', 9th ed., Eds. J. G. Hardman, L. E. Limbird, McGraw-Hill, New York, 1995.
32. K. Löf, J. Hovinen, P. Reinikainen, L. M. Vilpo, E. Seppälä, J. A. Vilpo, Chem. -Biol. Interact. 1997, 103, 187.
33. L. Panasci, J. -P. Paiement, G. Christodoulopoulos, A. Belenkov, A. Malapetsa, R. Aloyz, Clin. Cancer Res. 2001, 7, 454.
34. C. Salmelin, J. Hovinen, J. Vilpo, Mutat. Res. 2000, 467, 129.
35. C. Salmelin, J. Vilpo, Mutat. Res. 2003, 522, 33.
36. C. Salmelin, J. Vilpo, Mutat. Res. 2002, 500, 125.
37. R. R. Selzer, A. A. Elfarra, Carcinogenesis 1999, 20, 285.
38. B. A. Roe, J. S. Crabtree, A. S. Khan, 'DNA isolation and sequencing: Essential techniques', John Wiley & Sons, 1996, Chapter I.
39. A. J. Pawlowicz, T. Munter, Y. Zhao, L. Kronberg, Chem. Res. Toxicol. 2006, 19, 571.
40. T. L. Munter, L. Cottrell, S. Hill, L. Kronberg, W. P. Watson, P. T. Golding, Chem. Res. Toxicol. 2002, 15, 1549.