In vitro, in vivo, and in silico analyses of the antitumor activity of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazoles

Molecular Cancer Therapeutics

Volumn 3, Issue 12, 2004, Pages 1565-1575

  Leong, Chee Onn ^a   Suggitt, Marie ^b   Swaine, David J ^b   Bibby, Michael C ^b   Stevens, Malcolm F G ^a   Bradshaw, Tracey D ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF BRADFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 AMINO 3 METHYLPHENYL) 5 FLUOROBENZOTHIAZOLE; 5 FLUORO 2 (4 LYSYLAMINO 3 METHYLPHENYL)BENZOTHIAZOLE; 5F 203; ANTINEOPLASTIC AGENT; BENZOTHIAZOLE; CELL DNA; DOUBLE STRANDED DNA; PHOSPHATASE; PHOSPHOTRANSFERASE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER RESISTANCE; CARCINOMA CELL; CELL CYCLE; CELL STRAIN MCF 7; CLUSTER ANALYSIS; COMET ASSAY; COMPUTER MODEL; COMPUTER PROGRAM; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA ADDUCT; DNA DAMAGE; DNA STRAND BREAKAGE; DOSE TIME EFFECT RELATION; DRUG DETERMINATION; DRUG MECHANISM; DRUG RESPONSE; DRUG SELECTIVITY; DRUG SENSITIVITY; DRUG STRUCTURE; ENZYME REGULATION; FEMALE; HOLLOW FIBER; HUMAN; HUMAN CELL; IMPLANT; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PHARMACODYNAMICS; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL CYCLE; COMET ASSAY; COMPUTATIONAL BIOLOGY; CYTOCHROME P-450 CYP1A1; DNA ADDUCTS; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, NEOPLASM; FEMALE; HUMANS; MEMBRANES, ARTIFICIAL; MICE; MICE, NUDE; THIAZOLES; TIME FACTORS; TUMOR CELLS, CULTURED; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 12344263872     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. Bradshaw TD, Wrigley S, Shi D-F, Schultz RJ, Paull KD, Stevens MFG. 2-(4-Aminophenyl)benzothiazoles: novel agents with selective profiles of antitumour activity. Br J Cancer 1998;77:745-52.
2. Bradshaw TD, Shi D-F, Schultz RJ, et al. Influence of 2-(4-aminophenyl) benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo. Br J Cancer 1998;78:421-9.
3. Hutchinson I, Chua M-S, Browne HL, et al. Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles. J Med Chem 2001; 44:1446-55.
4. Bradshaw TD, Chua M-S, Browne HL, Trapani V, Sausville EA, Stevens MFG. In vitro evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles. Br J Cancer 2001;86:1348-54.
5. Kashiyama E, Hutchinson I, Chua M-S, et al. Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of C- and N-oxidation products of 2-(4-aminophenyl)benzothiazoles. J Med Chem 1999;42:4172-84.
6. Loaiza-Pérez AI, Trapani V, Hose C, et al. The AhR mediates sensitivity of MCF-7 breast cancer cells to the antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole. Mol Pharmacol 2002;61:13-9.
7. Chua M-S, Kashiyama E, Bradshaw TD, et al. Role of CYP1A1 in modulation of antitumor properties of the novel agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203, NSC 674495) in human breast cancer cells. Cancer Res 2000;60:5196-203.
8. Leong C-O, Gaskell M, Martin EA, et al. Antitumour 2-(4-aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo. Br J Cancer 2003;88:470-7.
9. Bradshaw TD, Bibby MC, Double JA, et al. Preclinical evaluation of amino acid prodrugs of novel antitumor 2-(4-amino-3-methylphenyl)benzothiazoles. Mol Cancer Ther 2002;1:239-46.
10. Hutchinson I, Jennings SA, Vishnuvajjala BR, Westwell AD, Stevens MFG. Antitumour benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs. J Med Chem 2002;45:744-7.
11. Soule HD, Vazquez J, Long A, Albert S, Brennan M. A human cell line from a pleural effusion derived from a breast carcinoma. J Natl Cancer Inst 1973;51:1409-16.
12. Cailleau R, Olive M, Cruciger QV. Long-term human breast carcinoma cell lines of metastatic origin: preliminary characterization. In vitro 1978;14:911-5.
13. O'Callaghan YC, Woods JA, O'Brien NM. Limitations of the single-cell gel electrophoresis assay to monitor apoptosis in U937 and HepG2 cells exposed to 7β-hydroxycholsterol. Biochem Pharmacol 2001; 61: 1217-26.
14. Helma C, Uhl M. A public domain imafe-analysis program for the single-cell gel-electrophoresis (comet) assay. Mutat Res 2000;466:9-15.
15. Hollingshead MG, Alley MC, Camalier RF, et al. In vivo cultivation of tumor cells in hollow fibers. Life Sci 1995;57:131-41.
16. UKCCR. Guidelines for the welfare of animals in experimental neoplasia. Br J Cancer 1998;77:1-10.
17. Mosmann T. Rapid colorimetric assay for cellular growth and survival: applications to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55-63.
18. Singh NP, McCoy MT, Tice RR, Schneider EL. A simple technique for quantitation of low levels of DNA damage in individual cells. Exp Cell Res 1988;175:184-91.
19. Ward TH, Butler J, Shahbakhti H, Richards JT. Comet assay studies on the activation of two diaziridinylbenzoquinones in K562 cells. Biochem Pharmacol 1997;53:1115-21.
20. Olive PL. DNA damage and repair in individual cells: applications of the comet assay in radiobiology. Int J Radiat Biol 1999;75:395-405.
21. Andreoli C, Leopardi P, Crebelli R. Detection of DNA damage in human lymphocytes by alkaline single cell gel electrophoresis after exposure to benzene or benzene metabolites. Mutat Res 1997;377:95-104.
22. Hannon-Fletcher MPA, O'Kane MJ, Moles KW, Weatherup C, Barnett CR, Barnett YA. Levels of peripheral blood cell DNA damage in insulin dependent diabetes mellitus human subjects. Mutat Res 2000;460: 53-60.
23. Martin FL, Cole KJ, Williams JA, Millar BC, Harvey D, Weaver G. Activation of genotoxins to DNA-damaging species in exfoliated breast milk cells. Mutat Res 2000;470:115-24.
24. Rabow AA, Shoemaker RH, Sausville EA, Covell DG. Mining the National Cancer Institute's tumor-screening database: identification of compounds with similar cellular activities. J Med Chem 2002;45: 818-40.
25. Kopjar N, Garaj-Vrhovac V, Miles I. Assessment of chemotherapy-induced DNA damage in peripheral blood leukocytes of cancer patients using the alkaline comet assay. Teratogenesis, Carcinogenesis Mutagenesis 2002;22:13-30.
26. Vernole P, Tedechi B, Caporossi D, Maccarrone M, Melino G, Annicchiarico-Petruzzelli M. Induction of apoptosis by bleomycin in resting and cycling human lymphocytes. Mutagenesis 1998;13: 209-15.
27. Harvathova E, Slamenova D, Hlincikova L, Mandal TK, Gabelova A, Collins AR. The nature and origin of DNA single strand breaks determined with the comet assay. Mutat Res 1998;409:163-71.
28. Donahue BA, Fuchs RPP, Reines D, Hanawalt PC. Effects of aminofluorene and acetylaminofluorene DNA adducts on transcriptional elongation by RNA polymerase II. J Biol Chem 1996;271:10588-94.
29. Hemmiki K, Judjum DB. Covalent modification of DNA by antineoplastic agents. J Natl Cancer Inst 1984;173:1021-8.
30. Benhamou S, Sarasin A. Variability in nucleotide excision repair and cancer risk: a review. Mutat Res 2000;462:149-58.
31. Braithwaite E, Wu X, Wang Z. Repair of DNA lesions: mechanisms and relative repair efficiencies. Mutat Res 1999;424:407-219.
32. Friedberg EC. DNA damage and repair. Nature 2003;421:436-40.
33. Wang JY. Cellular responses to DNA damage. Curr Opin Cell Biol 1998;10:240-7.
34. Monks A, Harris E, Hose C, Connelly J, Sausville EA. Genotoxic profiling of MCF-7 breast cancer cell line elucidates gene expression modifications underlying toxicity of the anticancer drug 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole. Mol Pharmacol 2003;6:766-72.
35. Chua M-S, Bradshaw TD, Stevens MFG. 2-(4-Aminophenyl)benzothiazoles: agents with selective and potent antitumour activity in vitro and in vivo. In: Fiebig HH, Burger AM, editors. Relevance of tumor models for anticancer drug development. Contrib Oncol Vol 54. Basel: Karger; 1999. p. 397-408.
36. 1/S transition and their response to DNA damage. FEBS Lett 2001;490:117-22.
37. Smith ML, Fornace AJ. Mammalian DNA damage-inducible genes associated with growth arrest and apoptosis. Mutat Res 1996;340: 109-24.
38. Choi J, Appella E, Donehower LA. The structure and expression of the murine wildtype p53-induced phosphatase 1 (Wip1) gene. Genomics 2000;64:298-306.
39. Fiscella M, Zhang HL, Fan S, et al. Wip1, a novel human protein phosphatase that is induced in response to ionising radiation in a p53-dependent manner. Proc Natl Acad Sci U S A 1997;94:6048-53.
40. Sasaki MS, Ejima Y, Tachibana A, et al. DNA damage response pathway in radioadaptive response. Mut Res 2002;504:101-18.
41. Ryan KM, Phillips AC, Vousden KH. Regulation and function of the p53 tumor suppressor protein. Curr Opin Cell Biol 2001;13:332-7.
42. Nichols AF, Itoh T, Zolezzi F, Hutsell S, Linn S. Basal transcriptional regulation of human damage specific DNA-binding protein genes DDB1 and DDB 2 by Spl, E2F, N-myc and NF1 elements. Nucleic Acids Res 2003;31:562-9.
43. Tang J, Chu G. Xeroderma pigmentosum complementation group E and UV-damaged DNA-binding protein. DNA Repair (Amst) 2002;1: 601-16.
44. Batty D, Rapic-Otrin V, Levine A, Wood R. Stable binding of human XPC complex to irradiated DNA confers strong discrimination for damaged sites. J Mol Biol 2000;300:275-90.
45. Moustacchi E. DNA damage and repair: consequences on dose-responses. Mutat Res 2000;464:35-40.
46. Pierce AJ, Stark JM, Araujo FD, Moynahan ME, Berwick M, Jasin M. Double-strand breaks and tumorigenesis. Trends Cell Biol 2001;11: S52-9.
47. Cedervall B, Persson L, Polischouk A, Lange CS. Perspective on biological dosimetry from the aspect of individual radiosensitivity: the context of DNA double-strand breaks and chromosomal aberrations. Appl Radiat Isot 2000;52:1117-20.
48. Vock EH, Lutz WK, Ilinskaya O, Vamvakas S. Discrimination between genotoxicity and cytotoxicity for the induction of DNA double-strand breaks in cells treated with aldehydes and diepoxides. Mutat Res 1999; 441:85-93.
49. Johnstone EC, Lind MJ, Griffin MJ, Boddy AV. Ifosfamide metabolism and DNA damage in tumour and peripheral blood lymphocytes of breast cancer patients. Cancer Chemother Pharmacol 2000;46: 433-41.