Permanent positive charge strongly influences DNA/RNAb indingand antiprolifer ativeactivity of ureae-phenanthridinium conjugates

European Journal of Medicinal Chemistry

Volumn 45, Issue 8, 2010, Pages 3281-3292

  Stojković, Marijana Radić ^a   Marczi, Saška ^b   Glavaš Obrovac, Ljubica ^b,c   Piantanida, Ivo ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY HOSPITAL OSIJEK   (Croatia)

^c JOSIP JURAJ STROSSMAYER UNIVERSITY OF OSIJEK   (Croatia)

Author keywords

Antiproliferative activity; DNA; Fluorescence selectivity; Intercalation; RNA; Urea phenanthridinium

Indexed keywords

1 (5,6 DIMETHYLPHENANTHRIDIN 8 YL) 3 [2 [3 (5,6 DIMETHYLPHENANTHRIDIN 8 YL)UREIDO]ETHYL]UREA HYDROGENSULFATE; 1 (5,6 DIMETHYLPHENANTHRIDIN 8 YL) 3 [6 [3 (5,6 DIMETHYLPHENANTHRIDIN 8 YL)UREIDO]ETHYL]UREA HYDROGENSULFATE; 1 (5,6 DIMETHYLPHENANTHRIDIN 8 YL) 3 [9 [3 (5,6 DIMETHYLPHENANTHRIDIN 8 YL)UREIDO]NONYLL]UREA HYDROGENSULFATE; 1 (6 METHYLPHENANTHRIDIN 8 YL) 3 [2 [3 (6 METHYLPHENANTHRIDIN 8 YL)UREIDO]ETHYL]UREA TRIHYDRATE; 1 (6 METHYLPHENANTHRIDIN 8 YL) 3 [6 [3 (6 METHYLPHENANTHRIDIN 8 YL)UREIDO]HEXYL]UREA TRIHYDRATE; 1 (6 METHYLPHENANTHRIDIN 8 YL) 3 [9 [3 (6 METHYLPHENANTHRIDIN 8 YL)UREIDO]NONYL]UREA; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG; UREA PHENANTHRIDINIUM;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CIRCULAR DICHROISM; CONTROLLED STUDY; DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTERCALATION COMPLEX; METHYLATION; RNA BINDING; THERMOSTABILITY;

EID: 77954311616     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.04.006     Document Type: Article

References (41)

1. R. B. Silverman,The Organic Chemistry of Drug Design and Drug Action. Elsevier Academic,Burlington,MA,2004.
2. M. Demeunynck,C. Bailly,W. D. Wilson,DNA and RNA Binders. Wiley-VCH,Weinheim,2002.
3. E. Trinquet,G. Mathis,Mol. Bio. Syst. 2 (2006) 380-387.
4. N. W. Luedtke,Q. Liu,Y. Tor,Chem. Eur. J. 11 (2005) 11495-11508.
5. T. Kubar,M. Hanus,F. Ryjacek,P. Hobza,Chem. Eur. J. 12 (2006) 280-290.
6. K. M. Langner,P. Kedzierski,W. A. Sokalski,J. Leszczynski,J. Phys. Chem. B 110 (2006) 9720-9727.
7. N. Stevens,N. O'Connor,H. Vishwasrao,D. Samaroo,E. R. Kandel,D. L Akins,C. M. Drain,N. J. Turro,J. Am. Chem. Soc. 130 (2008) 7182-7183.
8. C. Bailly,R. K. Arafa,F. A. Tanious,W. Laine,C. Tardy,A. Lansiaux,P. Colson,D. W. Boykin,W. D. Wilson,Biochemistry 44 (2005) 1941-1952
9. M. Maiti,G. S. Kumar,Med. Res. Rev. 27 (2007) 649-695.
10. (a)A. D. C. Parenty,L. V. Smith,K. M. Guthrie,D.-L. Long,J. Plumb,R. Brown,L Cronin,J. Med. Chem. 48 (2005) 4504-4506;
11. (b)I. Kock,D. Heber,M. Weide,U. Wolschendorf,B. Clement,J. Med. Chem. 48 (2005) 2772-2777
12. W. G. Lewis,L. G. Green,F. Grynszpan,Z. Radic,P. R. Carlier,P. Taylor,M. G. Finn,K. B. Sharpless,Angew. Chem. Int. Ed. 41 (2002) 1053-1057.
13. A. Krasinski,Z. Radic,R. Manetsch,J. Raushel,P. Taylor,K. B. Sharpless,H. C. Kolb,J. Am. Chem. Soc. 127 (2005) 6686-6692.
14. I. Piantanida,B. S. Palm,P. Cudic,M. Zinic,H.-J. Schneider,Tetrahedron Lett. 42 (2001) 6779-6783.
15. I. Piantanida,B. S. Palm,P. Cudic,M. Zinic,H.-J. Schneider,Tetrahedron 60 (2004) 6225-6231.
16. G. Malojcic,I. Piantanida,M. Marinic,M. Zinic,M. Marjanovic,M. Kralj,K. Pavelic,H.-J. Schneider,Org. Biomol. Chem. 3 (2005) 4373-4381.
17. W. C. Drewe,R. Nanjunda,M. Gunaratnam,M. Beltran,G. N. Parkinson,A. P. Reszka,W. D. Wilson,S. Neidle,J. Med. Chem. 51 (2008) 7751-7767.
18. G. W. Shipps,K. E. Pryor,J. Xian,D. A. Skyler,E. H. Davidson,J. Rebek,Proc. Natl. Acad. Sci. USA 94 (1997) 11833-11838
19. N. W. Luedtke,Q. Liu,Y. Tor,Bioorg. Med. Chem. 11 (2003) 5235-5247
20. E. De Clercq,Curr. Med. Chem. 8 (2001) 1543-1572.
21. M. Kozurková,D. Sabolová,L Janovec,J. Mikes,J. Koval',J. Ungvarský,M. Stefanisinová,P. Fedorocko,P. Kristian,J. Imrich,Bioorg. Med. Chem. 16 (2008) 3976-3984.
22. M. Radic Stojkovic,I. Piantanida,Tetrahedron 64 (2008) 7807-7814.
23. P. Cudic,M. Zinic,V. Tomisic,V. Simeon,J.-P. Vigneron,J.-M. Lehn,J. Chem. Soc. Chem. Commun. (1995) 1073-1075.
24. G. Scatchard,Ann. N. Y. Acad. Sci. 51 (1949) 660-672;
25. J. D. McGhee,P. H. von Hippel,J. Mol. Biol. 103 (1976) 665-679.
26. (a)H. Gampp,M. Maeder,C. J. Meyer,A. D. Zuberbuehler,Talanta 32 (1985) 257-264;
27. (b)M. Maeder,A. D. Zuberbuehler,Anal. Chem. 62 (1990) 2220-2224.
28. A. Rodger,B. Norden,Circular Dichroism and Linear Dichroism. Oxford University Press,New York,1997.
29. N. Berova,K. Nakanishi,R. W. Woody,Circular Dichroism Principles and Applications. Wiley-VCH,New York,2000.
30. M. Eriksson,B. Nordén,Methods in Enzymology 340 (2001) 68-98.
31. C. R. Cantor,P. R. Schimmel,Biophysical Chemistry. WH Freeman,San Francisco,CA,1980,pp. 1109-1181.
32. (a)E. C. Long,J. K. Barton,Acc. Chem. Res. 23 (1990) 271-273;
33. G. Dougherty,J. R. Pilbrow,Int. J. Biochem. 16 (1984) 1179-1192;
34. M. K. Pall,J. K. Ghosh,Spectrochimica. Acta (1995) 489-498.
35. C. Avendaño,J. C. Menéndez,Medicinal Chemistry of Anticancer Drugs. Elsevier Science,2008,pp. 200-201.
36. F. Zunino,G. Caranico,in: B. A. Teicher (Ed.),Cancer Therapeutics: Experimental and Clinical Agents,second ed. Humana Press Inc,Totowa,NJ,1997,pp. 195-202.
37. J. N. Miller,Standards for Fluorescence Spectrometry. Chapman and Hall,London,1981.
38. M. R. Eftink,Y. Jia,D. Hu,CA. Ghiron,J. Phys. Chem. 99 (1995) 5713-5723.
39. J. B. Chaires,N. Dattagupta,D. M. Crothers,Biochemistry 21 (1982) 3933-3940.
40. B. S. Palm,I. Piantanida,M. Zinic,H. J. Schneider,J. Chem. Soc,Perkin Trans. 2 (2000) 385-392.
41. G. Mickisch,S. Fajta,G. Keilhauer,E. Schlick,R. Tschada,P. Alken,Urol. Res. 18 (1990) 131-136.