Minor structural differences of monomethine cyanine derivatives yield strong variation in their interactions with DNA, RNA as well as on their in vitro antiproliferative activity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 13, 2009, Pages 4747-4755

  Glavaš Obrovac, Ljubica ^a,b   Piantanida, Ivo ^c   Marczi, Saška ^b   Mašić, Lozika ^c   Timcheva, Iliana I ^d   Deligeorgiev, Todor G ^e  

^a JOSIP JURAJ STROSSMAYER UNIVERSITY OF OSIJEK   (Croatia)

^b UNIVERSITY HOSPITAL OSIJEK   (Croatia)

^c RUDER BO KOVI INSTITUTE   (Croatia)

^d INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^e UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

Cellular uptake; Cytotoxicity; DNA RNA binding; Human normal and tumour cells; Monomethine cyanines

Indexed keywords

CELL NUCLEUS DNA; CYANINE DERIVATIVE; DOUBLE STRANDED RNA; MONOMETHINE CYANINE DERIVATIVE; RNA; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; AORTA; ARTICLE; BASE PAIRING; CELL PROLIFERATION; CELLULAR DISTRIBUTION; CHRONIC MYELOID LEUKEMIA; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DNA INTERACTION; DRUG SCREENING; ENDOTHELIUM CELL; FLUORESCENCE; HEMATOLOGIC MALIGNANCY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INTERCALATION COMPLEX; MOLECULAR INTERACTION; RNA BINDING; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; BINDING SITES; CATTLE; CELL LINE, TUMOR; CELL PROLIFERATION; DNA; HUMANS; MODELS, MOLECULAR; NEOPLASMS; NUCLEIC ACID DENATURATION; PYRIMIDINES; RNA; RNA, DOUBLE-STRANDED; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE; TITRIMETRY;

EID: 66449098500     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.070     Document Type: Article

References (34)

1. Trinquet E., and Mathis G. Mol. Bio. Syst. 2 (2006) 380
2. Benson S.C., Mathies R.A., and Glazier A.N. Nucleic Acids Res. 21 (1993) 5720
3. Benson S.C., Zeng Z., and Glazier A.N. Anal. Biochem. 231 (1995) 247
4. Smith L.M., Sanders J.Z., Kaiser R.J., Hughes P., Dodd C., Connell C.R., Heiner C., Kent S.B.H., and Hood L.E. Nature 321 (1986) 674
5. Prober J.M., Trainor G.L., Dam R.J., Hobbs F.W., Robertson C.W., Zagursky R.J., Cocuzza A.J., Jensen M.A., and Baumeister K. Science 238 (1987) 336
6. Li Y., and Glazer A.N. Bioconjugate Chem. 10 (1999) 241
7. Carnelly T.J., Barker S., Wang H., Tan W., and Le C. Chem. Res. Toxicol. 14 (2001) 1513
8. Denijn M., Schuurman H.-J., Jacobse K.C., and De Weger R.A. APMIS 100 (1992) 669
9. Wiegant J., Bezrookove V., Rosenberg C., Tanke H.J., Raap A.K., Zhang H., Bittner M., Trent J.M., and Meltzer P. Genome Res. 10 (2000) 861
10. Lipshutz R.J., Fodor S.P.A., Gingeras T.R., and Lockhart D.J. Nat. Genet. Suppl. 1 (1999) 20
11. Ferea T.L., and Brown P.O. Curr. Opin. Genet. Dev. 9 (1999) 715
12. In: Demeunynck M., Bailly C., and Wilson W.D. (Eds). DNA and RNA Binders (2002), Wiley-VCH, Weinheim
13. Cantor C.R., and Schimmel P.R. Biophysical Chemistry (1980), WH Freeman and Co., San Francisco 1109-1181
14. Wilson W.D., Ratmeyer L., Zhao M., Strekowski L., and Boykin D. Biochemistry 32 (1993) 4098
15. Timtcheva I., Maximova V., Deligeorgiev T., Zaneva D., and Ivanov I. J. Photochem. Photobiol. A: Chem. 130 (2000) 7
16. Deligeorgiev T., Gadjev N., Timtcheva I., Maximova V., Katerinopoulos H., and Foukaraki E. Dyes and Pigments 44 (2000) 131
17. Timtcheva I., Maximova V., Deligeorgiev T., Gadjev N., Drexhage K.H., and Petkova I. J. Photochem. Photobiol. B: Biol. 58 (2000) 130
18. Deligeorgiev T., Maximova V., Timtcheva I., Gadjev N., and Drexhage K.H. J. Fluoresc. 12 (2002) 225
19. Gadjev N., Deligeorgiev T., Timtcheva I., and Maximova V. Dyes and Pigments 57 (2003) 161
20. Deligeorgiev T., Timtcheva I., Maximova V., Jacobsen J.P., and Drexhage K.H. Dyes and Pigments 16 (2004) 79
21. Deligeorgiev T., Gadjev N., Vasilev A., Maximova V., Timtcheva I., Katerinopoulos H., and Tsikalas G. Dyes and Pigments 75 (2007) 466
22. Steiner-Biočić I., Glavaš-Obrovac L., Karner I., Piantanida I., Žinić M., Pavelić J., and Pavelić K. Anticancer Res. 16 (1996) 3705
23. Marczi S., Glavaš-Obrovac L., and Karner I. Chemotherapy 51 (2005) 217
24. Marczi S., Glavaš-Obrovac L., Belovari T., Stojković R., Ivanković S., Šerić V., Piantanida I., and Žinić M. Cancer Chemother. Pharmacol. 62 (2008) 595
25. McGhee J.D., and von Hippel P.H. J. Mol. Biol. 103 (1976) 679
26. Jain S.C., and Sobell H.M. J. Biomol. Struct. Dyn. 1 (1984) 1179
27. Nitta Y., and Kuroda R. Biopolymers 81 (2005) 376
28. Martinez R., and Chacón-García L. Curr. Med. Chem. 12 (2005) 127
29. Cooper T.M. Ther. Clin. Risk Manag. 3 (2007) 1135
30. Luchetti F., Gregorini A., Papa S., Burattini S., Canonico B., Velentini M., and Falcieri F. Haemalogica 83 (1998) 974
31. Hoffman M.R., Connors K.M., Meerson-Monosov A.Z., Herrera H., and Price J.H. Proc. Natl. Acad. Sci. 86 (1989) 2013
32. Chaires J.B., Dattagupta N., and Crothers D.M. Biochemistry 21 (1982) 3933
33. Malojčić, G.; Piantanida, I.; Marinić, M.; Žinić, M.; Marjanović, M.; Kralj, M.; Pavelić, K.; Schneider, H.-J. Org. Biomol. Chem., 2005, 3, 4373.
34. Mickisch G., Fajta S., Keilhauer G., Schlick E., Tschada R., and Alken P. Urol. Res. 18 (1990) 131