Interaction of cyanine dyes with nucleic acids. Spectral-luminescent properties of pyrylium and pyridinium mono/trimethincyanines

Authors

  • V. B. Kovalska Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • I. V. Valyukh Taras Shevchenko National University of Kyiv 64, Volodymyrska Str., Kyiv, Ukraine, 01033 Author
  • O. M. Kostenko Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • S. Yu. Dmitrieva Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • O. I. Tolmachov Institute of organic chemistry NAS of Ukraine 5, Murmanska Str., Kyiv, Ukraine, 02660 Author
  • S. M. Yarmoluk Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author

DOI:

https://doi.org/10.7124/bc.000633

Abstract

The spectral-luminescent properties of series of pyrylium and pyridinium mono- and trimethincyanines as possible fluorescent dyes for the nucleic acids (NA) detection and labeling were studied. We propose 3,6-methUendioxy-benzothiazolomonomethinepyridocy-anine MDO40 for using in homogeneous assay, as well as for the construction of otigonuleotides-based «light-up probes».

References

Haugland RP. Handbook of fluorescent probes and research chemicals. Molecular Probes Inc. Sixth ed. Eugene: OR, 1996. 680 p.

Svanvik N, Westman G, Wang D, Kubista M. Light-up probes: thiazole orange-conjugated peptide nucleic acid for detection of target nucleic acid in homogeneous solution. Anal Biochem. 2000;281(1):26-35.

Fan ZH, Mangru S, Granzow R, Heaney P, Ho W, Dong Q, Kumar R. Dynamic DNA hybridization on a chip using paramagnetic beads. Anal Chem. 1999;71(21):4851-9.

Whitcombe D, Newton CR, Little S. Advances in approaches to DNA-based diagnostics. Curr Opin Biotechnol. 1998;9(6):602-8.

Ishiguro T, Saitoh J, Yawata H, Otsuka M, Inoue T, Sugiura Y. Fluorescence detection of specific sequence of nucleic acids by oxazole yellow-linked oligonucleotides. Homogeneous quantitative monitoring of in vitro transcription. Nucleic Acids Res. 1996;24(24):4992-7.

Yarmoluk SM, Kostenko AM, Dubey IY. Interaction of cyanine dyes with nucleic acids. Part 19: new method for the covalent labeling of oligonucleotides with pyrylium cyanine dyes. Bioorg Med Chem Lett. 2000;10(19):2201-4.

Yarmoluk SM, Losytskyy MYu, Kovatska VB, Tomachynski SM, Ogutchansky TYu, Kostenko OM, Kurdyukov VV, Tolmachev OI. Interaction of cyanine dyes with nucleic acids. New (pyrido)(thio)trimethincyanine dye CCyan 40 for fluorescent labeling of oligonucleotides. Biopolym Cell. 2002; 18(4):340-6.

Yarmoluk SM, Zhyvoloup AN, Koval'ska VB, Klimenko IV, Kukharenko AP, Kovtun YP, Slominsky YL. Interaction of cyanine dyes with nucleic acids. I. Studies on monomethyne cyanine dyes as possible fluorescent probes for the detection of nucleic acids. Biopolym Cell. 1996; 12(1):69-74.

Yarmoluk SM, Kovalska VB, Smirnova TV, Shandura MP, Kovtun YP, Matsuka GKh. Interaction of cyanine dyes with nucleic acids. 2. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange. Biopolym Cell. 1996; 12(6):74-81.

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.

Kiprianov AI. The color and structure of polymethine dyes. Kiev: Naukova Dumka. 1979; 666 p.

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Published

2002-11-20

Issue

Vol. 18 No. 6 (2002)

Section

Bioorganic Chemistry