Biological properties of 4-methyl-2,7-diamino-5,10-diphenyl-4,9- diazapyrenium hydrogensulfate (ADAP)

Cancer Chemotherapy and Pharmacology

Volumn 62, Issue 4, 2008, Pages 595-604

  Marczi, Saška ^a   Glavaš Obrovac, Ljubica ^a,b   Belovari, Tatjana ^b   Stojković, Ranko ^c   Ivanković, Siniša ^c   Šerić, Vatroslav ^a   Piantanida, Ivo ^c   Žinić, Mladen ^c  

^a UNIVERSITY HOSPITAL OSIJEK   (Croatia)

^b School of Medicine Osijek   (Croatia)

^c RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

4,9 Diazapyrenium derivatives; Cellular uptake; Cytotoxicity in vitro; Intracellular distribution; Mice; Topoisomerase II ; Toxicity in vivo

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 4 METHYL 2,5 DIAMINO 5,10 DIPHENYL 4,9 DIAZAPYRENIUM HYDROGENSULFATE; ANTINEOPLASTIC AGENT; DNA TOPOISOMERASE (ATP HYDROLYSING);

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASSAY; BLOOD ANALYSIS; C H RAS GENE; C KI RAS GENE; C MOS GENE; C N RAS GENE; CANCER INHIBITION; CASPASE 3 GENE; CELL FREE SYSTEM; CELL NUCLEUS; CELL PROLIFERATION; CELL STRAIN CACO 2; CELL STRAIN MCF 7; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOPLASM; DRUG CYTOTOXICITY; DRUG DNA BINDING; DRUG MECHANISM; DRUG SCREENING; DRUG TUMOR LEVEL; ENZYME ASSAY; FLUORESCENCE MICROSCOPY; GENE EXPRESSION; HELA CELL; HEP 2 CELL; HUMAN; HUMAN CELL; IMMUNOBAND DEPLETION ASSAY; IN VITRO STUDY; IN VIVO STUDY; INTERCALATION COMPLEX; MALE; MORPHOLOGY; MOUSE; NONHUMAN; ONCOGENE; P53 GENE; PRIORITY JOURNAL; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

ADENOCARCINOMA; AMINOQUINOLINES; ANIMALS; ANTINEOPLASTIC AGENTS; CACO-2 CELLS; CELL LINE, TUMOR; CELL SURVIVAL; COLONIC NEOPLASMS; DNA TOPOISOMERASES, TYPE II; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; FORMAZANS; GENE EXPRESSION; HUMANS; INTERCALATING AGENTS; MALE; MICE; MICE, INBRED C3H; QUINOLINIUM COMPOUNDS; RNA, MESSENGER; TETRAZOLIUM SALTS;

EID: 47549117733     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-007-0643-0     Document Type: Article

References (52)

1. Ferlay J, Parkin MD, Pisani P (1998) Globocan: Cancer incidence and mortality worldwide. International Agency for Research on Cancer, IARC Cancer Base, Lyon, France, pp 3
2. Howard CV, Newby JA (2004) Could the increase in cancer incidence be related to recent environmental changes. In: Nicolopoulou-Stamati P, Hens L, Howard CV, Van Larebeke L (eds) Cancer as an environmental disease. Kluwer, Dordrecht
3. Q Li W Xu 2005 Novel anticancer targets in drug discovery in postgenomic age Curr Med Chem Anticancer Agents 5 53 63
4. LS Lerman 1961 Structural considerations in the interaction of DNA and acridines J Mol Biol 3 18 30
5. Demeunyck M, Bailly C, Wilson WD (2002) DNA and RNA binders: from small molecules to drugs. Wiley, New York
6. Silverman RB (2004) The organic chemistry of drug design and drug action, 2nd edn. Elsevier, San Diego
7. IW Taylor BK Milthorpe 1980 An evaluation of DNA fluorochromes, staining techiques and analysis for flow cytometry J Histochem Cytochem 28 11 1224 1232
8. SC Benson RA Mathies AN Glazer 1993 Heterodimeric DNA-binding dyes designed for energy transfer: stability and applications of the DNA complexes Nucleic Acids Res 21 24 5720 5726
9. T Biver A De Biasi F Secco M Venturini S Yarmoluk 2005 Cyanine dyes as intercalating agents: kinetic and thermodinamic studies on the DNA/Cyan40 and DNA/CCyan2 systems Biophys J 89 374 383
10. XL Yang AH-J Wang 1999 Structural studies of atom-specific drugs on DNA Pharmacol Ther 83 181 215
11. MF Brańa M Cacho A Gradillas B Pascual-Teresa A Ramos 2001 Intercalators as anticancer drugs Curr Pharm Des 7 1745 1780
12. R Martinez L Chacon-Garcia 2005 The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work Curr Med Chem 12 2 127 151
13. Subramanian D, Sommer FC, Muller MT (2001) ICE Bioassay. In: Osheroff N, Bjornsti M-A (eds) DNA Topoisomerase protocols. Enzymology and drugs. Humana Press, Totowa, pp 137-147
14. JE Ehlert MHG Kubbutat 2001 Apoptosis and its relevance in cancer therapy Onkologie 24 433 440
15. LH Hurley 2002 DNA and its associated processes as targets for cancer therapy Nat Rev Cancer 2 188 200
16. N Akimitsu K Kamura S Toné A Sakaguchi A Kikuchi H Hamamoto K Sekimizu 2003 Induction of apoptosis by depletion of topoisomerase II in mammalian cells Biochem Biophys Res Commun 307 301 307
17. B Kaina 2003 DNA damage-triggered apoptosis: critical role of DNA repair, double-strand breaks, cell proliferation and signaling Biochem Pharmacol 66 1547 1554
18. BS Palm I Piantanida M Žinić H-J Schneider 2000 The interaction of new 4,9-diazapyrenium compounds with double stranded nucleic acids J Chem Soc - Perkin Trans II 385 392
19. I Piantanida V Tomšić M Žinić 2000 4,9-Diazapyrenium cations. Synthesis, physico-chemical properties and binding of nucleotides in water J Chem Soc Perkin Trans II 375 383
20. I Piantanida BS Palm M Žinić H-J Schneider 2001 A new 4,9-diazapyrenium intercalator for single- and double-stranded nucleic acids: distinct differences from related diazapyrenium compounds and ethidium bromide J Chem Soc Perkin Trans II 9 1808 1816
21. D-H Yu J MacDonald S Josephs Q Liu V Nguy Y Tor F Wong-Staal Q-X Li 2006 MDDD, a 4,9-diazapyrenium derivative, is selectively toxic to glioma cells by inducing growth arrest at G0/G1 independently of p53 Invest New Drugs 24 489 498
22. I Steiner-Biočić L Glavaš-Obrovac I Karner I Piantanida M Žinić K Pavelić J Pavelić 1996 4,9-Diazapyrenium dications induce apoptosis in human tumor cells Anticancer Res 16 3705 3708
23. S Roknić L Glavaš-Obrovac I Karner I Piantanida M Žinić K Pavelić 2000 In vitro cytotoxicity of three 4,9-diazapyrenium hydrogensulfate derivatives on different human tumor cell lines Chemotherapy 46 143 149
24. S Marczi L Glavaš-Obrovac I Karner 2005 Induction of apoptosis of human tumor cells by a 4,9-diazapyrenium derivative and its effects on topoisomerase-II action Chemotherapy 51 217 222
25. I Piantanida M Žinić S Marczi L Glavaš-Obrovac 2007 Bis-4,9-diazapyrenium dications: synthesis of the methylenedibenzyl-analogue, interactions with nucleotides, DNA, RNA. The antitumor activity of all till now prepared analogues J Phys Org Chem 20 285 295
26. G Mickisch S Fajta G Keilhauer E Schlick R Tschada P Alken 1990 Chemosensitivity testing of primary human renal cell carcinoma by a tetrazolium based microculture assay (MTT) Urol Res 18 131 136
27. Burden DA, Froelich-Ammon J, Osheroff N (2001) Topoisomerase I-mediated cleavage of plasmid DNA. In: Osheroff N, Bjornsti M-A (eds) DNA topoisomerase protocols. Enzymology and drugs. Humana Press Inc., New Yersey, pp 283-289
28. Kaufmann SH, Svingen PA (2001) Immunoblot analysis and bend depletion assay. In: Bjornsti M-A, Osheroff N (eds), DNA topoisomerase protocols. DNA topology and enzymes. Humana Press Inc., New Yersey, pp 253-268
29. UK Laemmli 1970 Cleavage of structural proteins during the assembly of head of bacteriophage T4 Nature 227 680 685
30. L Gedda M Silvander S Sjöberg W Tjarks J Carlsson 1997 Cytotoxicity and subcellular localization of boronated phenanthridinium analogues Anticancer Drug Des 12 671 685
31. A Haldane GJ Finlay MP Hay WA Denny BC Baguley 1999 Cellular uptake of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) Anticancer Drug Des 14 275 280
32. KO Hicks FB Pruijn BC Baguley WR Wilson 2001 Extravascular transport of the DNA intercalator and topoisomerase poison N-[2-(dimethylamino)ethyl] acridine-4-carboxamide (DACA): diffusion and metabolism in multicellular layers of tumor cells J Pharmacol Exp Ther 297 1088 1098
33. A Lansiaux L Dassonneville M Facompré A Kumar CE Stephens M Bajic F Tanious WD Wilson DW Boykin C Bailly 2002 Distribution of furamidine analogues in tumor cells: influence of the number of positive charges J Med Chem 45 1994 2002
34. S Cline N Osheroff 1999 Cytosine arabinoside lesions are position-specific topoisomerase II poisons and stimulate DNA cleavage mediated by the human type II enzymes J Biol Chem 274 29740 29743
35. Rowe TC, Grabowski D, Ganapathi R (2001) Isolation of covalent enzyme-DNA complexes. In: Osheroff N, Bjornsti M-A (eds) DNA topoisomerase protocols. Enzymology and drugs. Humana Press Inc, New Jersey, pp 129-136
36. SG Kim M Sung KW Kang SH Kim MH Son WB Kim 2001 DA-125, a novel anthracycline derivative showing high-affinity DNA binding and topoisomerase II inhibitory activities, exerts cytotoxicity via c-Jun N-terminal kinase pathway Cancer Chemother Pharmacol 47 511 518
37. C Bal B Baldeyrou F Moz A Lansiaux P Colson L Kraus-Berthier S Leonce A Pierre M-F Boussard A Rousseau M Wierzbicki C Bailly 2004 Novel antitumor indenoindole derivatives targeting DNA and topoisomerase II Biochem Pharmacol 68 1911 1922
38. KL Marsh E Willmore S Tinelli M Cornarotti EL Mectes G Capranico LM Fisher CA Austin 1996 Amsacrine-promoted DNA cleavage site determinants for the two human DNA topoisomerase II isoforms alpha and beta Biochem Pharmacol 52 1675 1685
39. GJ Finlay GJ Atwell BC Baguley 1999 Inhibition of the action of the topoisomerase II poison amsacrine by simple aniline derivatives: evidence for drug-protein interactions Oncol Res 11 6 249 254
40. N Yew M Strobel GF Vande Woude 1993 Mos and the cell cycle: the molecular basis of the transformed phenotype Curr Opin Genet Dev 3 1 19 25
41. K Fukasawa GF Vande Woude 1997 Synergy between the Mos/mitogen-activated protein kinase pathway and loss of p53 function in transformation and chromosome instability Mol Cell Biol 17 1 506 518
42. SK Lyons AR Clarke 1997 Apoptosis and carcinogenesiy Br Medical Bull 53 554 569
43. S Djelloul M-E Forgue-Lafitte B Hermelin M Mareel E Bruyneel A Baldi A Giordano E Chastre C Gespach 1997 Enterocyte differentiation is compatible with SV40 large T expression and loss of p53 function in human colonic Caco-2 cells FEBS Lett 406 234 242
44. EC Pietsch O Humbey ME Murphy 2006 Polymorphisms in the p53 pathway Oncogene 25 1602 1611
45. CB Thompson 1995 Apoptosis in the pathogenesis and treatment of disease Science 267 1456 1462
46. MW Mayo CY Wang PC Cogswell KS Rogers-Graham SW Lowe CJ Der AS Baldwin Jr 1997 Requirement of NF-κB activation to suppress p53-independent apoptosis induced by oncogenic Ras. Science 278 1812 1815
47. P Shapiro 2001 Ras-MAP kinase signaling pathways and control of cell proliferation: relevance to cancer therapy Crit Rev Clin Lab Sci 39 4-5 285 330
48. A Moon 2006 Differential functions of Ras for malignant phenotypic conversion Arch Pharm Res 29 2 113 122
49. RL Ward AV Todd F Santiago T O'Connor NJ Hawkins 1997 Activation of the K-ras oncogene in colorectal neoplasms is associated with decreased apoptosis Cancer 79 6 1106 1113
50. J Downward 1998 ras signaling and apoptosis Curr Opin Genet Dev 8 49 54
51. C Bowen HJ Voeller K Kikly EP Gelmann 1999 Synthesis of procaspase-3 and -7 during apoptosis in prostate cancer cells Cell Death Differ 6 394 401
52. Moore DM (2000) Hematology of the mouse. In: Feldman BV, Zinkl JG, Jain NC (eds) Schalm's veterinary hematology. Lippincot Williams & Wilkons, Philadelphia, pp 1219-1224