Intercalation binding of 4-butylaminopyrimido[4′,5′:4,5] selenolo (2,3-b)quinoline to DNA: Relationship with in vitro cytotoxicity

Spectroscopy Letters

Volumn 37, Issue 4, 2004, Pages 347-366

  Gopal, M ^a   Veeranna, S ^a   Doddamani, L S ^b  

^a KUVEMPU UNIVERSITY   (India)

^b KARNATAK UNIVERSITY   (India)

Author keywords

4 Butylaminopyrimido 4 ,5 :4,5 selenolo(2,3 b) quinoline; Binding model; CD spectroscopy; Cytotoxicity; DNA; Ellipticine; UV spectroscopy

Indexed keywords

4 BUTYLAMINOPYRIMIDO[4',5':4,5]SELENOLO[2,3 B]QUINOLINE; ANTINEOPLASTIC AGENT; CYTOSINE; DNA; DNA FRAGMENT; DOUBLE STRANDED DNA; ELLIPTICINE; GUANINE; QUINOLINE DERIVATIVE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CELL LINE; CIRCULAR DICHROISM; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOTOXICITY; DNA HELIX; DRUG MECHANISM; FLUORESCENCE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INTERCALATION COMPLEX; IONIC STRENGTH; LUMINESCENCE; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; ULTRAVIOLET SPECTROSCOPY; VISCOSITY;

EID: 4444369341     PISSN: 00387010     EISSN: None     Source Type: Journal    
DOI: 10.1081/SL-120039469     Document Type: Article

References (47)

1. Frei, E.; Bieler, C.A.; Arlt, V.M.; Wiessler, M.; Stiborova, M. Covalent binding of the anticancer drug ellipticine to DNA in V79 cells transfected with human cytochrome p450 enzymes. Biochem. Pharmacol. 2002, 64, 289-295.
2. Auclair, C. Multimodal action of antitumor agents on DNA: the ellipticine series. Archs. Biochem. Biophys. 1987, 259, 1-14.
3. Singh, M.P.; Hill, G.C.; Peoch, D.; Rayner, B.; Inabach, J.L.; Lown, J.W. High-field NMR and restrained molecular modeling studies on a DNA heteroduplex containing a modified apurine abasic site in the form of covalently linked 9-aminoellipticine. Biochemistry 1994, 33, 10,271-10,285.
4. Chu, Y.; Hsu, M.T. Ellipticine increases the superhelical density of intracellular SV40 DNA by intercalation. Nucl. Acids 1992, 20, 4033-4038.
5. Monnot, M.; Mauffret, O.; Simon, V.; Lescot, E.; Psaume, B.; Saucier, J.M.; Charra, M.; Belehradek, J., Jr.; Fermandjian, S. DNA-Drug recognition and effects on topoisomerase II-mediated cytotoxicity: a three-mode binding model for ellipticine derivatives. J. Biol. Chem. 1991, 25, 1820-1829.
6. Fosse, P.; Rene, B.; Charra, M.; Paoletti, C.; Saucier, J. Stimulation of topoisomerase II-mediated DNA cleavage by ellipticine derivatives: Structure-activity relationships. Mol. Pharmacol. 1992, 42, 590-595.
7. Froelich-Ammon, S.J.; Patchan, M.W.; Osheoff, N.; Thompson, R.B. Topoisomerase II binds to ellipticine in the absence or presence of DNA: characterization of enzyme-drug interaction by fluorescence spectroscopy. J. Biol. Chem. 1995, 270, 14,998-15,004.
8. 53 protein phosphorylation by 9-hydroxyellipticine: a possible anticancer mechanism. Jpn. J. Cancer Res. 1995, 86, 819-829.
9. Nandeeshaiah, S.K.; Ambekar, S.Y. Synthesis, Dimroth rearrangment and blood platelet disaggregation property of pyrimido[4′,5′:4,5] selenolo(2,3-b)quinolines: a new class of condensed quinoline. Indian J. Chem. 1998, 37, 995-1000.
10. Gopal, M.; Shahabuddin, M.S.; Inamdar, S.R. Interaction between an 8-methoxy pyrimido[4′,5′:4,5]thieno(2,3-b)quinoline-4(3H) one antitumour drug and deoxyribo nucleic acid. Proc. Indian Acad. Sci. (Chem. Sci). 2002, 114, 687-696.
11. Gopal, M.; Shenoy, S.; Doddamani, L.S. Antitumor activity of 4-amino and 8-methyl-4(3diethylaminopropylamino)pyrimido[4′,5′:4,5]thieno-(2, 3-b)quinolines. J. Photochem. Photobiol. B 2003, 72, 69-78.
12. Gopal, M.; Shahabuddin, M.S. Antitumour activity of 8-methoxypyrimido [4′,5′:4,5]thieno(2,3-b)quinoline-4(3H)one. Kuvempu Univ. Sci. J. 2001, 1 (1), 36-40.
13. Clark, L.C.; Hixson, L.J.; Combs, G.F., Jr.; Reid, M.W.; Turbull, B.W.; Sampliner, R.E. Plasma selenium concentration predicts the prevalence of colorectal adenomatous polyps. Cancer Epidemiol. Biomarkers Prev. 1993, 2, 41-46.
14. Van den Brandt, P.A.; Goldbohm, R.A.; Vant't Veer, P.; Bode, P.; Dorant, E.; Hermus, R.J.; Sturmans, F. A prospective cohort study on selenium status and the risk of lung cancer. Cancer Res. 1993, 53, 4860-4865.
15. Rayman, M.P. The importance of selenium to human health. Lancet 2000, 356, 233-241.
16. Meydani, M.; Vitamin E. Lancet 1995, 345, 170-175.
17. Helzlsouer, K.J.; Alberg, A.J.; Norkus, E.P.; Morris, J.S.; Hoffman, S.C.; Comstock, G.W. Prospective study of serum micronutrients and ovarian cancer. J. Natl. Cancer Inst. 1996, 88, 32-37.
18. Clark, L.C.; Combs, J.F.J.; Turbull, B.W.; Slate, E.H.; Chalker, D.K.; Chow, J.; Davis, L.S.; Glover, R.A.; Graham, G.F.; Gross, E.G.; Krongrad, A.; Lesher, H.L.J.; Park, H.K.; Sanders, B.B.J.; Smith, C.L.; Taylor, J.R. Effects of selenium supplementation for cancer prevention in patients with carcinoma of the skin: a randomized controlled trial. Nutritional prevention of cancer study group. JAMA 1996, 276, 1957-1963.
19. Guttenplan, J.B.; Kosinska, W.; Pressentin, M.D.M.; Rosa, J.; El-Bayoumy, K. Effects of 1,4-phenylenebis(methylene)selenocyanate (p-XSC) and vitamin E on 4-nitroquinoline-N-oxide (4-NQO)-induced mutagenesis in lacZ mouse upper aerodigestive tissue. Mutat. Res. 2002, 518, 85-93.
20. Ip, C.; Lisk, D.J.; Ganther, H.; Thompson, H.J. Triphenylselenonium and diphenylselenide in cancer chemoprevention: comparative studies of anticarcinogenic efficacy, tissue selenium levels, and excretion profile. Anticancer Res. 1997, 17, 3195-3200.
21. Schatchard, G. The attraction of proteins for small molecules and ions. Ann. NY Acad. Sci. 1949, 51, 660-672.
22. Peacocke, A.R.; Skerrett, J.N.H. The interaction of aminoacridines with nucleic acids. Trans. Faraday Soc. 1956, 52, 261.
23. McGhee, J.D.; von-Hipple, D.H. Theoretical aspects of DNA protein interactions: Co-operative and non co-operative binding of large ligands to a one-dimensional homogeneous lattice. J. Mol. Biol. 1974, 86, 469-489.
24. Son, G.-S.; Yeo, J.-A.; Kim, J.-M.; Kim, S.K.; Moon, H.R.; Nam, W. Base specific complex formation of norflaxacin with DNA. Biophys. Chem. 1998, 74, 225-236.
25. Lee, E.-J.; Yeo, J.-A.; Lee, G.-J.; Han, S.-W.; Kim, S.K. Amine group of guanine enhances the binding of norflaxacin antibiotics to DNA. Eur. J. Biochem. 2000, 267, 6018-6024.
26. Maiti, M.; Nandi, R.; Chaudhari, K. Interaction of sanguinarine with natural and synthetic deoxyribonucleic acids. Indian J. Biochem. Biophys. 1994, 21, 158-165.
27. Le Mee, S.; Pierr, A.; Markovits, J.; Atassi, G.; Jacquemin-Sablon, A.; Saucier, J.-M. S16020-2, a new highly cytotoxic antitumor olivacine derivative: DNA interaction and DNA topoisomerase II inhibition. Mol. Pharmacol. 1998, 53, 213-220.
28. Lakowicz, J.R. Principles of Fluorescence Spectroscopy, 2nd Ed.; Plenum: New York, 1999; 238-265.
29. Lee, E.-J.; yeo, J.-A.; Jung, K.; Hwangbo, H.J.; Lee, G.-J.; Kim, S.K. Enantioselective binding of ofloxacin to B form DNA. Archs. Biochem. Biophys. 2001, 395, 21-24.
30. Benesi, H.A.; Hilderbrand, J.H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 1949, 71, 2703-2707.
31. Waring, M.J. DNA modification and Cancer. Annu. Rev. Biochem. 1981, 50, 159-192.
32. Cohen, G.; Eisenberg, H. Viscosity and sedimentation study of sonicated DNA-proflavin complexes. Biopolymers 1969, 8, 45-55.
33. Norden, B.; Kubista, M.; Kurucser, T. Linear dichroism spectroscopy of nucleic acids. Q. Rev. Biophys. 1992, 25, 51-170.
34. Yarmoluk, S.M.; Lukashov, S.S.; Losytskyy, M.Yu.; Akerman, B.; Kornyushyna, O.S. Interaction of cyanine dyes with nucleic acids XXVI. Intercalation of the trimethine cyanine dye cyan2 into double-stranded DNA: study by spectral luminescence methods. Spectrochim. Acta A 2002, 58, 3223-3232.
35. Bourdouxhe, C.; Colson, P.; Houssier, C.; Sun, J.; Montenay-Garestier, T.; Helene, C.; Rivalle, C.; Bisagni, E.; Waring, M.J.; Henichart, J.; Bailly, C. Binding of a distamycin-ellipticine hybrid molecule to DNA and chromatin: spectroscopic, biochemical and molecular modeling investigations. Biochemistry 1992, 31, 12385-12396.
36. Schwaller, A.; Aubard, J.; Auclair, C.; Paoletti, C.; Dodin, G. The G: C base-pair preference of 2-N-metyl 9-hydroxyellipticinium. Eur. J. Biochem. 1989, 181, 129-134.
37. Monnot, M.; Mauffret, O.; Lescot, E.; Fermandjian, S. Probing intercalation and conformational effects of the anticancer drug 2-methyl-9-hydroxyellipticinium acetate in DNA fragments with circular dichroism. Eur. J. Biochem. 1992, 204, 1035-1039.
38. Frederick, C.A.; Williams, L.D.; Ughetto, G.; Vandermarel, G.A.; VanBoom, J.H.; Rich, A.; Wang, A.H.-J. Structural comparison of anticancer drug-DNA complexes: Adriamycin and daunomycin. Biochemistry 1990, 29, 2538-2549.
39. Virgil, H.D., Jr.; Jonathan, A.; Pachter; Stanley, T.C. DNA binding studies on several new anthracycline antitumour antibiotics II. The importance of the carbomethoxy-group at position-10 of the class II anthracycline molecule. Mol. Pharmacol. 1979, 16, 623-632.
40. Baez, A.; Gonzalez, F.A.; Vazouez, D.; Waring, M.J. Interaction between a 3-nitrobenzothiazolo(3,2-a)quinolinium antitumour drug and deoxyribonucleic acid. Biochem. Pharmacol. 1983, 32, 2089-2094.
41. El-Bayoumy, K. The protective role of selenium on genetic damage and on cancer. Mutation Res. 2001, 475, 123-139.
42. Ganther, H.E. Selenium metabolism and mechanisms of cancer prevention. Adv. Exp. Med. Biol. 2001, 492, 119-130.
43. Fosse, P.; Rene, B.; Le Bret, M.; Paoletti, C.; Saucier, J.M. Sequence requirements for mammalian topoisomerase II mediated DNA cleavage stimulated by an ellipticine derivative. Nucl. Acids Res. 1991, 19, 2861-2868.
44. Nelson, E.M.; Tewey, K.M.; Liu, L.F. Mechanism of antitumor drug action: poisoning of mammalian DNA topoisomerase II on DNA by 4′-(9- acridinylamino)-methanesulfon-m-anisidide. Proc. Natl. Acad. Sci. USA. 1984, 81, 1361-1365.
45. Ross, W.; Rowe, T.; Glisson, B.; Yalowich, J.; Liu, L. Role of topoisomerase II in mediating epipodophyllotoxin-induced DNA cleavage. Cancer Res. 1984, 44, 5857-5860.
46. Liu, L.F.; Rowe, T.C.; Yang, L.; Tewey, K.M.; Chen, G.L. Cleavage of DNA by mammalian DNA topoisomerase II. J. Biol. Chem. 1983, 258, 15365-15370.
47. Burden, D.A.; Osheroff, N. Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme. Biochim. Biophys. Acta 1998, 1400, 139-154.