Spectral Properties and DNA-binding Study of 6a, 12a-Diazadibenzo-[a,g]fluorenylium Derivative

• Autorzy: Juskowiak B. , Gałęzowska E. , Kościelna H. , Hermann T. , Piotrowska K.
• Języki publikacji: EN

Abstrakty

EN

The DNA binding affinity and anion effect on the aggregation of a G-quadruplex selective ligand, 6a,12a-diazadibenzo-[a,g]fluorenylium derivative, were studied by UV-Vis absorption, molecular modeling and fluorescence spectroscopy. The anion character and its concentration influenced the spectral properties of ligand aggregates. Observed spectral peculiarities were discussed in terms of the formation of H- and J-type aggregates. The DNA binding mode and affinity of the ligand depended on the salt concentration; preferential binding to G-quadruplexDNAwas clearly seen at higher salt concentration.

Słowa kluczowe

EN

aggregation; fluorescence; fluorenylium derivative; DNA-binding; G-quadruplex DNA; intercalation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 5
• Strony: 831--844
• Opis fizyczny: Bibliogr. 38 poz., rys.

Twórcy

autor

Juskowiak B.

• Department of Analytical Chemistry, Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznań, Poland

autor

Gałęzowska E.

• Department of Analytical Chemistry, Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznań, Poland

autor

Kościelna H.

• Department of Analytical Chemistry, Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznań, Poland

autor

Hermann T.

• Department of Physical Chemistry, K. Marcinkowski University of Medical Sciences, Poznañ, Poland

autor

Piotrowska K.

• Department of Physical Chemistry, K. Marcinkowski University of Medical Sciences, Poznañ, Poland

Bibliografia

• 1.Wilson W.D., Reversible interactions of nucleic acids with small molecules, in: Blackburn G.M. and Gait M.J. (Eds.), Nucleic acids in chemistry and biology (Chapter 8), IRL Press, New York, 1990.
• 2.Simonsson T., Biol. Chem., 368, 621 (2001).
• 3.Arthanari H. and Bolton P.H., Chem. Biol., 8,221 (2001).
• 4.Neidle S. and Parkinson G., Nat. Rev. Drug Discovery, 1, 383 (2002).
• 5.Siddiqui-Jain A., Grand C.L., Bearss D.J. and Hurley L.H., Proc. Natl. Acad. Sci. U.S.A., 99, 11593 (2002).
• 6.Zakian V.A., Science, 270, 1601 (1995).
• 7.Neidle S. and Parkinson G.N., Curr. Opin. Struct. Biol., 13, 275 (2003).
• 8.Lingner J., Hughes T.R., Shevchenko A., Mann M., Lundblad V. and Cech T.R., Science, 276, 561 (1997) .
• 9.Kelland L.R., Anticancer Drugs, 11, 503 (2000).
• 10.Lee H., Blasco M.A., Gottlieb G.J., Homer J.W., Greider C.W. and DePinho R.A., Nature, 392, 569 (1998) .
• 11.Counter C.M., Hahn W.C., Wei W., Caddie S.D., Beijersbergen R.L., Lansdorp P.M., Sedivy J.M. and Weinberg R.A., Proc. Natl. Acad. Sci. U.S.A., 95, 14723 (1998).
• 12.Neidle S. and Kelland L.R., Anti-Cancer Drug Des., 14, 341 (1999).
• 13.Mergny J.-L., Riou J.-F., Maillict P., Teulade-Fichou M.-P. and Gilson E., Nucl. Acids Res., 30, 839 (2002).
• 14.Sun D., Thompson B., Cathers B.E., Salazar M., Kerwin S.M., Trent J.O., Jenkins T.C., Neidle S. and Hurley L.H., J. Med. Chem., 40, 2113 (1997).
• 15.Izbicka E., Wheelhouse R.T., Raymond E., Davidson K.K., Lawrence R.A., Sun D., Windle B„ Hurley L.H. and Von Hoff D.D., Cancer Res., 59, 639 (1999).
• 16.Harrison R.J., Gowan S.M., Kelland L.R. and Neidle S., Bioorg. Med. Chem. Lett., 9, 2463 (1999).
• 17.Fedoroff O.Y., Salazar M., Han H., Chemeris V.V., Kerwin S.M. and Hurley L.H. Biochemistry 12367(1998).
• 18.Read M.A., Wood A.A., Harrison J.R., Gowan S.M., Kelland L.R., Dosanjh H.S. and Neidle S., J. Chem., 42,4538(1999).
• 19.Neidle S., Harrison R.J., Reszka A.P. and Read M.A., Pharmacol. Ther., 85, 133 (2000).
• 20.Juskowiak B., Galezowska E., Koczorowska N. and Hermann T.W., Bioorg. Med. Chem. Lett., 14, (2004).
• 21.Hermann T.W., Girreser U., Michalski P. and Piotrowska K., Arch. Pharm. Pharm. Med. Chem., 4 (2002).
• 22.http://paris.chem.yale.edu/extinct.html.
• 23.Scatchard G„ Am. N. Y. Acad. Sci., 51, 660 (1949).
• 24.Stewart J.J.P., Quant. Chem. Prog. Exch., 10, 86 (1990).
• 25.Ridley J. and Zemer M.C., Theoret. Chim. Acta, 42, 223 (1976).
• 26.The program CAChe is available from FQS Poland (http://www.fgspl.com.pl).
• 27.Kerwin S.M., Chen G., Kern J.T. and Thomas P.W., Bioorg. Med. Chem. Lett., 12, 447, 3395 (2000)
• 28.Juskowiak B., Galezowska E. and Takenaka S., Spectrochim. Acta A, 59, 1083 (2003).
• 29.Sambrook J., Fritsch E.F. and Maniatis T., Molecular Cloning: A Laboratory Manual, CSHL Pres; vol. 3,E10-E16(1989).
• 30.Kapuscinski J. and Darzankiewicz Z., J. Biomol. Struct. Dyn., 5, 127 (1987).
• 31.Slama-Schwok A., Jazwinski J., Bere A., Montenay-Garestier M., Rougee M., Helene C. and Lehn J Biochemistry, 28, 3227 (1989).
• 32.Zee-Cheng R.K. and Cheng C.C., J. Med. Chem., 21, 199 (1978).
• 33.Kasha M., Rawls H.R. and Ashraf EI-Bayoumi M., Pure Appl. Chem., 11,371 (1965).
• 34.Wilson G.S., Q. Rev. Biophys., 2, 179 (1978).
• 35.Wilson W.D., Krishnamoorthy C.R., Wang Y.H. and Smith J.C., Biopolymers, 24, 1941 (1985).
• 36.Li W., Wu P., Ohmichi T. and Sugimoto N., FEES Lett., 526, 77 (2002).
• 37.Read M.A. and Neidle S., Biochemistry, 39, 13422 (2000).
• 38.Kern J.T., Thomas P.W. and Kerwin S.M., Biochemistry, 41, 11379 (2002).