Biopolym. Cell. 2001; 17(3):242-248.
Bioorganic Chemistry
Interaction of cyanine dyes with nucleic acids. 22. Spectral-luminescent properties of monomethyne pyrylium and pyrymidinium cyanines and their DNA-complexes
1Lukashov S. S., 2Kachkovskyy G. O., 2Losytskyy M. Yu., 1Yarmoluk S. M.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680
  2. Taras Shevchenko National University of Kyiv
    64, Volodymyrska Str., Kyiv, Ukraine, 01033


We have obtained a number of pairs of monomethyne cyanines, dyes of each pair having similar structure and contrary direction of electric dipole moment, and investigated the spectral-luminescent properties of these dyes in free state and in the presence of double-stranded DMA. The change in values of the dyes Stockes shifts under the interaction with DMA is the evidence for the location of the dyes within DMA complexes in dipole medium, that confirms the «half-intercalation» interaction model. Considering the changes of the dyes Stockes shifts under the interaction with DNA as the manifestation of changes in electronic asymmetry of these dyes, we made an assumption about the location of each dye inside the DNA. It has been concluded, that the dye molecule orientation in the DNA-complex is defined by the dye geometry, its dipole moment direction being of minor importance.


[1] Rye HS, Yue S, Wemmer DE, Quesada MA, Haugland RP, Mathies RA, Glazer AN. Stable fluorescent complexes of double-stranded DNA with bis-intercalating asymmetric cyanine dyes: properties and applications. Nucleic Acids Res. 1992;20(11):2803-12.
[2] Skeidsvoll J, Ueland PM. Analysis of double-stranded DNA by capillary electrophoresis with laser-induced fluorescence detection using the monomeric dye SYBR green I. Anal Biochem. 1995;231(2):359-65.
[3] Suzuki T, Fujikura K, Higashiyama T, Takata K. DNA staining for fluorescence and laser confocal microscopy. J Histochem Cytochem. 1997;45(1):49-53.
[4] Ogul'chansky TYu, Yashchuk VM, Yarmoluk SM, Losytskyy MYu. Interaction of cyanine dyes with nucleic acids. 14. Spectral peculiarities of several monomethyne benzothiazole cyanine dyes and their interaction with DNA. Biopolym Cell. 2000; 16(5):345-55.
[5] Lerman LS. The structure of the DNA-acridine complex. Proc Natl Acad Sci U S A. 1963;49:94-102.
[6] Pritchard NJ, Blake A, Peacocke AR. Modified intercalation model for the interaction of amino acridines and DNA. Nature. 1966;212(5068):1360-1.
[7] Rye HS, Glazer AN. Interaction of dimeric intercalating dyes with single-stranded DNA. Nucleic Acids Res. 1995;23(7):1215-22.
[8] Nord?n B. Optical studies on complexes between DNA and pseudoisocyanine. Biophys Chem. 1976;6(1):31-45.
[9] Long EC, Barton JK. On demonstrating DNA intercalation. Acc Chem Res. 1990;23(9):271–3.
[10] Kumar CV, Turner RS, Asuncion EH. Groove binding of a styrylcyanine dye to the DNA double helix: the salt effect. J Photochem Photobiol A Chem. 1993;74(2-3):231–8.
[11] Milanovich N, Suh M, Jankowiak R, Small GJ, Hayes JM. Binding of TO-PRO-3 and TOTO-3 to DNA: Fluorescence and Hole-Burning Studies. J Phys Chem. 1996;100(21):9181–6.
[12] Yarmoluk SM, Kovalska VB, Kovtun YuP. Interaction of cyanine dyes with nucleic acids. 5. Towards model of «half intercalation of monomethyne cyanine dyes into double-stranded nucleic acids. Biopolym Cell. 1999; 15(1):75-82.
[13] Lukashov SS, Losytskii MYu, Yarmoluk SM, Slominskii YL. The interaction of cyanine dyes with nucleic acids. 12. Novel monomethyne cyanines based on the 5,6-methylenedioxy-benzothiazole and spectral-luminescent properties of thier complexes with nucleic acids. Biopolym Cell. 2000; 16(6):562-72.
[14] Kelemen J, Wizinger R. Uber alkylsubstituierte Pyrylo- und Pyridino-cyanine 1. 2,6-Dimethylpyrylo- und 2,6-Dimethyl- pyridino-cyanine aus 2,6-DimethyI-i-pyron. Helv chim acta. 1962; 45(6):1908-1917.
[15] Maniatis T, Fritsch EF, Sambrook I. Molecular cloning: A laboratory manual. New York: Cold Spring Harbor Lab. publ., 1982. 458 p.
[16] ORGANIKUM. Organisch-chemisches Grundpraktikum. Eds Becker H, VEB Deutscher Verlag der Wissenschaften Berlin 1990
[17] Ishchenko AA. Structure and spectral-luminescent properties of polymethyne cyanine dyes. Kyiv: Naukova dumka 1994. 232 p.