Minor structural modifications to alchemix influence mechanism of action and pharmacological activity

Biochemical Pharmacology

Volumn 83, Issue 11, 2012, Pages 1514-1522

  Abdallah, Qasem M A ^a   Phillips, Roger M ^a   Johansson, Fredrik ^b,c   Helleday, Thomas ^c   Cosentino, Laura ^a   Abdel Rahman, Hamdy ^a   Etzad, Jasarat ^a   Wheelhouse, Richard T ^a   Kiakos, Konstantinos ^d   Bingham, John P ^d   Hartley, John A ^d   Patterson, Laurence H ^a   Pors, Klaus ^a  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

^b KAROLINSKA INSTITUTE   (Sweden)

^c STOCKHOLM UNIVERSITY   (Sweden)

^d UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Anthraquinone; H2AX phosphorylation; MDR; NER; p53; Topoisomerase II

Indexed keywords

ALCHEMIX; ANTHRAQUINONE DERIVATIVE; DNA TOPOISOMERASE (ATP HYDROLYSING); ICT 2901; ICT 2902; ICT 2903; PROTEIN P53; UNCLASSIFIED DRUG;

ANIMAL CELL; APOPTOSIS; ARTICLE; CELL CYCLE G1 PHASE; CELL DEATH; CELL STRAIN HCT116; CHO CELL; CONTROLLED STUDY; CYTOTOXICITY; DNA ALKYLATION; DNA BINDING; DNA REPAIR; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTHRAQUINONES; ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL DEATH; CHO CELLS; CRICETINAE; DNA ADDUCTS; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, NEOPLASTIC; HCT116 CELLS; HISTONES; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84859492098     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2012.02.017     Document Type: Article

References (40)

1. J.W. Lown Anthracycline and anthraquinone anticancer agents: current status and recent developments Pharmacol Ther 60 1993 185 214
2. K.C. Murdock, R.G. Child, P.F. Fabio, R.B. Angier, R.E. Wallace, and F.E. Durr Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones J Med Chem 22 1979 1024 1030
3. R.K. Johnson, R.K. Zee-Cheng, W.W. Lee, E.M. Acton, D.W. Henry, and C.C. Cheng Experimental antitumor activity of aminoanthraquinones Cancer Treat Rep 63 1979 425 439
4. R.K. Zee-Cheng, A.E. Mathew, P.L. Xu, R.V. Northcutt, and C.C. Cheng Structural modification study of mitoxantrone (DHAQ). Chloro-substituted mono- and bis[(aminoalkyl)amino]anthraquinones J Med Chem 30 1987 1682 1686
5. A.P. Krapcho, J.J. Landi Jr., K.J. Shaw, D.G. Phinney, M.P. Hacker, and J.J. McCormack Synthesis and antitumor activities of unsymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones and related systems J Med Chem 29 1986 1370 1373
6. A.P. Krapcho, Z. Getahun, K.L. Avery Jr., K.J. Vargas, M.P. Hacker, and S. Spinelli Synthesis and antitumor evaluations of symmetrically and unsymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones and 1,4-bis[(aminoalkyl)amino]-5,8-dihydroxyanthracene-9,10-diones J Med Chem 34 1991 2373 2380
7. B. Stefanska, M. Dzieduszycka, S. Martelli, and E. Borowski Synthesis of unsymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones as potential antileukemic agents J Med Chem 32 1989 1724 1728
8. E.M. Leslie, R.G. Deeley, and S.P. Cole Multidrug resistance proteins: role of P-glycoprotein, MRP1, MRP2, and BCRP (ABCG2) in tissue defense Toxicol Appl Pharmacol 204 2005 216 237
9. K. Ueda, A. Yoshida, and T. Amachi Recent progress in P-glycoprotein research Anticancer Drug Des 14 1999 115 121
10. G.D. Leonard, T. Fojo, and S.E. Bates The role of ABC transporters in clinical practice Oncologist 8 2003 411 424
11. T.K. Li, and L.F. Liu Tumor cell death induced by topoisomerase-targeting drugs Annu Rev Pharmacol Toxicol 41 2001 53 77
12. K. Chikamori, D.R. Grabowski, M. Kinter, B.B. Willard, S. Yadav, and R.H. Aebersold Phosphorylation of serine 1106 in the catalytic domain of topoisomerase II alpha regulates enzymatic activity and drug sensitivity J Biol Chem 278 2003 12696 12702
13. K. Pors, Z. Paniwnyk, K.C. Ruparelia, P.H. Teesdale-Spittle, J.A. Hartley, and L.R. Kelland Synthesis and biological evaluation of novel chloroethylaminoanthraquinones with potent cytotoxic activity against cisplatin-resistant tumor cells J Med Chem 47 2004 1856 1859
14. K. Pors, S.D. Shnyder, P.H. Teesdale-Spittle, J.A. Hartley, M. Zloh, and M. Searcey Synthesis of DNA-directed pyrrolidinyl and piperidinyl confined alkylating chloroalkylaminoanthraquinones: potential for development of tumor-selective N-oxides J Med Chem 49 2006 7013 7023
15. K. Pors, Z. Paniwnyk, P. Teesdale-Spittle, J.A. Plumb, E. Willmore, and C.A. Austin Alchemix: a novel alkylating anthraquinone with potent activity against anthracycline- and cisplatin-resistant ovarian cancer Mol Cancer Ther 2 2003 607 610
16. M. Ponti, S.M. Forrow, R.L. Souhami, M. D'Incalci, and J.A. Hartley Measurement of the sequence specificity of covalent DNA modification by antineoplastic agents using Taq DNA polymerase Nucleic Acids Res 19 1991 2929 2933
17. K.R. Fox Methods in molecular biology. 90. Drug-DNA interaction protocols 1997 Humana Press Totowa, N.J
18. R.T. Wheelhouse, S.A. Jennings, V.A. Phillips, D. Pletsas, P.M. Murphy, and N.C. Garbett Design, synthesis, and evaluation of novel biarylpyrimidines: a new class of ligand for unusual nucleic acid structures J Med Chem 49 2006 5187 5198
19. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J Immunol Methods 65 1983 55 63
20. F. Johansson, A. Allkvist, K. Erixon, A. Malmvarn, R. Nilsson, and A. Bergman Screening for genotoxicity using the DRAG assay: investigation of halogenated environmental contaminants Mutat Res 563 2004 35 47
21. W.B. Mattes, J.A. Hartley, and K.W. Kohn DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards Nucleic Acids Res 14 1986 2971 2987
22. P.J. Smith, N.J. Blunt, R. Desnoyers, Y. Giles, and L.H. Patterson DNA topoisomerase II-dependent cytotoxicity of alkylaminoanthraquinones and their N-oxides Cancer Chemother Pharmacol 39 1997 455 461
23. M. Bakker, J. Renes, A. Groenhuijzen, P. Visser, H. Timmer-Bosscha, and M. Muller Mechanisms for high methoxymorpholino doxorubicin cytotoxicity in doxorubicin-resistant tumor cell lines Int J Cancer 73 1997 362 366
24. J. Cummings, J.S. Macpherson, I. Meikle, and J.F. Smyth Development of anthracenyl-amino acid conjugates as topoisomerase I and II inhibitors that circumvent drug resistance Biochem Pharmacol 52 1996 979 990
25. A. Masta, P.J. Gray, and D.R. Phillips Molecular basis of nitrogen mustard effects on transcription processes: role of depurination Nucleic Acids Res 22 1994 3880 3886
26. H. Lage, E. Aki-Sener, and I. Yalcin High antineoplastic activity of new heterocyclic compounds in cancer cells with resistance against classical DNA topoisomerase II-targeting drugs Int J Cancer 119 2006 213 220
27. A.J. Levine p53, the cellular gatekeeper for growth and division Cell 88 1997 323 331
28. B. Vogelstein, D. Lane, and A.J. Levine Surfing the p53 network Nature 408 2000 307 310
29. P.M. O'Connor, J. Jackman, I. Bae, T.G. Myers, S. Fan, and M. Mutoh Characterization of the p53 tumor suppressor pathway in cell lines of the National Cancer Institute anticancer drug screen and correlations with the growth-inhibitory potency of 123 anticancer agents Cancer Res 57 1997 4285 4300
30. C.F. Cheok, C.S. Verma, J. Baselga, and D.P. Lane Translating p53 into the clinic Nat Rev Clin Oncol 8 2011 25 37
31. B. Ogretmen, and A.R. Safa Expression of the mutated p53 tumor suppressor protein and its molecular and biochemical characterization in multidrug resistant MCF-7/Adr human breast cancer cells Oncogene 14 1997 499 506
32. S. Bai, and D.W. Goodrich Different DNA lesions trigger distinct cell death responses in HCT116 colon carcinoma cells Mol Cancer Ther 3 2004 613 619
33. J.L. Guerriero, D. Ditsworth, Y. Fan, F. Zhao, H.C. Crawford, and W.X. Zong Chemotherapy induces tumor clearance independent of apoptosis Cancer Res 68 2008 9595 9600
34. J.A. Hickman, and C.C. Boyle Apoptosis and cytotoxins Br Med Bull 53 1997 632 643
35. W.M. Bonner, C.E. Redon, J.S. Dickey, A.J. Nakamura, O.A. Sedelnikova, and S. Solier GammaH2AX and cancer Nat Rev Cancer 8 2008 957 967
36. A.Z. Al-Minawi, Y.F. Lee, D. Hakansson, F. Johansson, C. Lundin, and N. Saleh-Gohari The ERCC1/XPF endonuclease is required for completion of homologous recombination at DNA replication forks stalled by inter-strand cross-links Nucleic Acids Res 37 2009 6400 6413
37. I.U. De Silva, P.J. McHugh, P.H. Clingen, and J.A. Hartley Defects in interstrand cross-link uncoupling do not account for the extreme sensitivity of ERCC1 and XPF cells to cisplatin Nucleic Acids Res 30 2002 3848 3856
38. L. Savolainen, T. Cassel, and T. Helleday The XPD subunit of TFIIH is required for transcription-associated but not DNA double-strand break-induced recombination in mammalian cells Mutagenesis 25 2010 623 629
39. K. Caldecott, and P. Jeggo Cross-sensitivity of gamma-ray-sensitive hamster mutants to cross-linking agents Mutat Res 255 1991 111 121
40. C. Lundin, N. Schultz, C. Arnaudeau, A. Mohindra, L.T. Hansen, and T. Helleday RAD51 is involved in repair of damage associated with DNA replication in mammalian cells J Mol Biol 328 2003 521 535