A Monomethine Cyanine Dye Cyan 40 for Two-photon-excited Fluorescence Detection of Nucleic Acids and Their Visualization in Live Cells

Photochemistry and Photobiology

Volumn 77, Issue 2, 2003, Pages 138-145

  Ohulchanskyy, Tymish Y ^a   Pudavar, Haridas E ^a   Yarmoluk, Sergiy M ^b   Yashchuk, Valeriy M ^c   Bergey, Earl J ^a   Prasad, Paras N ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b INSTITUTE OF MOLECULAR BIOLOGY AND GENETICS   (Ukraine)

^c TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

CYAN 40; CYANINE DYE; DNA; MONOMETHINE CYANINE DYE; RNA; UNCLASSIFIED DRUG; CARBOCYANINE; NUCLEIC ACID;

ARTICLE; CELL VIABILITY; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; EMBRYO; FLUORESCENCE ANALYSIS; HUMAN; HUMAN CELL; MICROFLUOROMETRY; NUCLEIC ACID ANALYSIS; PHOTON; PROTEIN ANALYSIS; STAINING; CELL CULTURE; CHEMISTRY; METHODOLOGY; SPECTROFLUOROMETRY;

CARBOCYANINES; HUMANS; NUCLEIC ACIDS; PHOTONS; SPECTROMETRY, FLUORESCENCE; TUMOR CELLS, CULTURED;

EID: 0038672776     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2003)077<0138:AMCDCF>2.0.CO;2     Document Type: Article

References (39)

1. Bhawalkar, J. D., G. S. He and P. N. Prasad (1996) Nonlinear multiphoton processes in organic and polymeric materials. Rep. Prog. Phys. 59(9), 1041-1070.
2. Reinhardt, B. A., L. L. Brott, S. J. Clarson, A. G. Dillard, J. C. Bhatt, R. Kannan, L. Yuan, G. S. He and P. N. Prasad (1998) Highly active two-photon dyes: design, synthesis, and characterization toward application. Chem. Mater. 10(7), 1863-1874.
3. Wu, L.-Z., X.-J. Tang, M.-H. Jiang and C.-H. Tung (1999) Two-photon induced fluorescence of novel dyes. Chem. Phys. Lett. 315, 379-382.
4. Fakis, M., J. Polyzos, G. Tsigaridas, J. Parthenios, A. Fragos, V. Giannetas, P. Persephonis and J. Mikroyannidis (2000) Novel class of pyrylium dyes with high efficiency in lasing and two-photon absorption fluorescence. Chem. Phys. Lett. 323, 111-116.
5. Wang, H. Z., H. Lei, Z. C. Wei, F. L. Zhao, X. G. Zheng, N. S. Hu, X. M. Wang, Y. Ren, Y. P. Tian, Q. Fang and M. H. Jiang (2000) Spectral properties and effective upconverted lasing of new organic molecules. Chem. Phys. Lett. 324, 349-353.
6. Ehrlich, J. E., X. L. Wu, L. Y. S. Lee, Z. Y. Hu, H. Rockel, S. R. Marder and J. W. Perry (1997) Two-photon absorption and broadband optical limiting with bis-donor stilbenes. Opt. Lett. 22, 1843-1845.
7. So, P. T. C., C. Y. Dong, B. R. Master and K. M. Berland (2000) Two-photon excitation fluorescence microscopy. Annu. Rev. Biomed. Eng. 2, 399-429.
8. Konig, K., U. Simon and K. J. Halbhuber (1996) 3D resolved two-photon fluorescence microscopy of living cells using a modified confocal laser scanning microscope. Cell. Mol. Biol. 42, 1181-1194.
9. Konig, K. (2000) Multiphoton microscopy in life sciences. J. Microsc. 200(2), 83-104.
10. Denk, W., J. Strickler and W. Webb (1990) Two-photon fluorescence scanning microscopy. Science 248, 73-76.
11. Wang, X., L. J. Krebs, M. Al-Nuri, H. E. Pudavar, S. Ghosal, C. Liebow, A. A. Nagy, A. V. Schally and P. N. Prasad (1999) A chemically labeled cytotoxic agent: two-photon fluorophore for optical tracking of cellular pathway in chemotherapy. Proc. Natl. Acad. Sci. USA (Chem.) 96, 11081-11084.
12. Wang, X., H. E. Pudavar, R. Kapoor, L. J. Krebs, E. J. Bergey, C. Liebow, P. N. Prasad, A. A. Nagy and A. V. Schally (2001) Studies on the mechanism of action of a targeted chemotherapeutic drug in living cancer cells by two photon laser scanning microspectrofluorometry. J. Biomed. Opt. 6(3), 319-325.
13. Dedov, V. N., G. C. Cox and B. D. Roufogalis (2001) Visualisation of mitochondria in living neurons with single- and two-photon fluorescence laser microscopy. Micron 32(7), 653-660.
14. Diaspro, A. and M. Robello (2000) Two-photon excitation of fluorescence for three-dimensional optical imaging of biological structures. J. Photochem. Photobiol. B: Biol. 55(1), 1-8.
15. Sonnleitner, M., G. J. Schutz and Th. Schmidt (1999) Imaging individual molecules by two-photon excitation. Chem. Phys. Lett. 300, 221-226.
16. Van Orden, A., H. Cai, P. M. Goodwin and R. A. Keller (1999) Efficient detection of single DNA fragments in flowing sample streams by two-photon fluorescence excitation. Anal. Chem. 71, 2108-2116.
17. Gryczynski, I., H. Malak and J. R. Lakowicz (1996) Multiphoton excitation of the DNA stains DAPI and Hoechst. Bioimaging 4, 138-148.
18. Malak, H., F. N. Castellano, I. Gryczynski and J. R. Lakowicz (1997) Two-photon excitation of ethidium bromide labeled DNA. Biophys. Chem. 67(1-3), 35-41.
19. Haughland, R. P. (1999) Molecular Probes. Handbook of Fluorescent Probes and Research Chemicals. Molecular Probes, Inc., Eugene, OR.
20. Konig, K., H. Liang, M. W. Bems and B. J. Tromberg (1995) Cell damage by near-IR microbeams. Nature 377, 20-21.
21. Hopt, A. and E. Neber (2001) Highly nonlinear photodamage in two-photon fluorescence microscopy. Biophys. J. 80(4), 2029-2036.
22. Mishra, A., K. R. Behera, P. K. Behera, B. K. Mishra and G. B. Behera (2000) Cyanines during the 1990s: a review. Chem. Rev. 100, 1973-2011.
23. Timtcheva, I., V. Maximova, T. Deligeorgiev, D. Zaneva and I. Ivanov (2000) New asymmetric monomethine cyanine dyes for nucleic acid labeling: absorption and fluorescence spectral characteristics. J. Photochem. Photobiol. A: Chem. 130, 7-11.
24. Rye, H. S., S. Yue, D. E. Wemmer, M. A. Quesada, R. P. Haughland, R. A. Mathies and A. N. Glazer (1992) Stable fluorescent complexes of double-stranded DNA with bis-intercalating asymmetric cyanine dyes: properties and applications. Nucleic Acids Res. 20, 2803-2812.
25. Gurrieri, S., K. S. Wells, I. D. Johnsom and C. Bustamante (1997) Direct visualization of individual DNA molecules by fluorescence microscopy: characterization of the factors affecting signal/background and optimization of imaging conditions using YOYO. Anal. Biochem. 249, 44-53.
26. Bianco, P. R., L. R. Brewer, M. Corzett, R. Balhorn, Y. Yeh, S. C. Kowalczykowski and R. J. Baskin (2001) Processive translocation and DNA unwinding by individual RecBCD enzyme molecules. Nature 409, 374-378.
27. Zucker, R. M., A. P. Keshaviah, O. T. Price and J. M. Goldman (2000) Confocal laser scanning microscopy of rat follicle development. J. Histochem. Cytochem. 48, 781-791.
28. Idziorek, T., J. Estaquier, F. De Bels and J. C. Ameisen (1995) YOPRO-1 permits cytofluorometric analysis of programmed cell death (apoptosis) without interfering with cell viability. J. Immunol. Methods 185, 249-258.
29. Yarmoluk, S. M., V. B. Kovalska, T. V. Smirnova, M. P. Shandura, Yu. P. Kovtun and G. Kh. Matsuka (1996) Interaction of cyanine dyes with nucleic acids. II. Spectroscopic properties of methyleneoxy analogues of Thiazole Orange. Biopolym. Cell 12, 74-81.
30. Ogul'chansky, T. Yu., S. M. Yarmoluk, V. M. Yashchuk and M. Yu. Losytskyy (1999) The spectral response on DNA interaction with some monomethyne cyanine dyes. In Spectroscopy of Biological Molecules: New Directions (Edited by J. Greve, G. J. Puppels and C. Otto), pp. 309-310, Kluwer Academic Publishers, Boston, MA.
31. Yarmoluk, S. M. and I. Ya. Dubey (1997) Interaction of cyanine dyes with nucleic acids. 3. The use of new cyanine dyes Cyan 13 and Cyan 40 for detection of nucleic acids in agarose gel. Biopolym. Cell 13(5), 419-421.
32. Yarmoluk, S. M., D. B. Kryvorotenko and V. B. Kovalska (2001) Interaction of cyanine dyes with nucleic acids. XX. New methods for the preparation of fluorescent probes based on benzothiazol-4-(2,6-dimethylpyridinium) cyanine dyes. Dyes Pigm. 48(3), 165-172.
33. Yarmolyuk, S. M., V. B. Kovalska, D. V. Kryvorotenko, A. O. Balanda and T. Yu. Ogul'chansky (2001) Interaction of cyanine dyes with nucleic acids. XXV. Influence of affinity-modifying groups in the structure of benzothiazol-4-(2,6-dimethylpyridinium) dyes on the spectral properties of the dyes in the presence of nucleic acids. Spectrochim. Acta Part A 57, 1533-1540.
34. Ogul'chansky, T. Yu., V. M. Yashchuk, M. Yu. Losytskyy, I. O. Kocheshev and S. M. Yarmoluk (2000) Interaction of cyanine dyes with nucleic acids. XVII. Towards an aggregation of cyanine dyes in solutions as a factor facilitating nucleic acid detection. Spectrochim. Acta Part A 56, 805-814.
35. Ketemen, J. and R. Wizinger (1962) Über alkylsubstituierte pyrylo- und pyridino-cyanine 1. 2,6-dimethylpyrylo- und 2,6-dimethylpyridinocyanine aus 2,6-dimethyl-g-pyron. Helv. Chim. Acta 45, 1908-1917.
36. Edmondson, J. M., L. S. Armstrong and A. O. Martinez (1988) A rapid and simple MTT-based spectrophotometric assay for determining drug sensitivity in monolayer cultures. J. Tissue Cult. Methods 11(6), 15-17.
37. Xu, C. and W. W. Webb (1996) Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 nm to 1050 nm. J. Opt. Soc. Am. B 13(3), 481-491.
38. Cosa, G., K.-S. Foscaneanu, J. R. N. McLean, J. P. McNamee and J. C. Scaiano (2001) Photophysical properties of fluorescent DNA-dyes bound to single- and double-stranded DNA in aqueous buffered solution. Photochem. Photobiol. 73(6), 585-599.
39. Busch, H. and K. Smetana (1970) The Nucleolus. Academic Press, New York.