Characterization of a series of far-red-absorbing thiobarbituric acid oxonol derivatives as fluorescent probes for biological applications

Analytical Biochemistry

Volumn 317, Issue 1, 2003, Pages 47-58

  Klonis, Nectarios ^a,b   Quazi, Nurul H ^a,b   Deady, Les W ^a,b   Hughes, Andrew B ^a,b   Tilley, Leann ^a,b  

^a LA TROBE UNIVERSITY   (Australia)

^b Department of Civil and Environmental Engineering   (Australia)

Author keywords

Antibody label; DNA label; Fluorescent probes; Oxonol

Indexed keywords

BIOSYNTHESIS; DNA; FLUORESCENCE; OLIGONUCLEOTIDES; ORGANIC POLYMERS; PROBES;

ABSORPTION WAVELENGTHS; BIOLOGICAL APPLICATIONS; FLUORESCENT PROBES; OLIGONUCLEOTIDE CONJUGATES; OXONOL; RESEARCH APPLICATIONS; SPECTRAL PROPERTIES; THIOBARBITURIC ACID;

CHROMOPHORES;

FLUORESCENT DYE; ORGANIC SOLVENT; PYRIDINIUM DERIVATIVE; THIOBARBITURIC ACID DERIVATIVE;

ABSORPTION; AQUEOUS SOLUTION; ARTICLE; CHROMATOPHORE; CONCENTRATION RESPONSE; DRUG SCREENING; DRUG SYNTHESIS; PRIORITY JOURNAL; QUANTUM CHEMISTRY; TIME;

EID: 0242418204     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0003-2697(03)00086-1     Document Type: Article

References (42)

1. Patonay G., Antoine M.D. Near-infrared fluorogenic labels: new approach to an old problem. Anal. Chem. 63:1991;321A-327A.
2. Thompson R.B. Lakowicz J.R. Topics in Fluorescence Spectroscopy. Volume 4: Probe Design and Chemical Sensing. 1994;151-181 Plenum Press, New York.
3. Stoyanov S. Probes: dyes fluorescing in the NIR region. Pract. Spectrosc. 25:2001;35-93.
4. Southwick P.L., Ernst L.A., Tauriello E.W., Parker S.R., Mujumdar R.B., Mujumdar S.R., Clever H.A., Waggoner A.S. Cyanine dye labeling reagents: carboxymethylindocyanine succinimidyl esters. Cytometry. 11:1990;418-430.
5. Mujumdar R.B., Ernst L.A., Mujumdar S.R., Lewis C.J., Waggoner A.S. Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters. Bioconjugate Chem. 4:1993;105-111.
6. A.S. Waggoner, L.A. Ernst, R.B. Mujumdar, Method for labeling and detecting materials employing arylsulfonate cyanine dyes, 1993, US Patent No. 5,268,486.
7. Ballou B., Fisher G.W., Hakala T.R., Farkas D.L. Tumor detection and visualization using cyanine fluorochrome-labeled antibodies. Biotechnol. Prog. 13:1997;649-658.
8. Cullander C. Imaging in the far-red with electronic light microscopy: requirements and limitations. J. Microsc. 176:1994;281-286.
9. Schena M., Shalon D., Davis R.W., Brown P.O. Quantitative monitoring of gene expression patterns with a complementary DNA microarray. Science. 270:1995;467-470.
10. MacBeath G., Schreiber S.L. Printing proteins as microarrays for high-throughput function determination. Science. 289:2000;1760-1763.
11. Wang Y., Wang X., Guo S.W., Ghosh S. Conditions to ensure competitive hybridization in two-color microarray: a theoretical and experimental analysis. Biotechniques. 32:2002;1342-1346.
12. Ballou B., Fisher G.W., Deng J.S., Hakala T.R., Srivastava M., Farkas D.L. Cyanine fluorochrome-labeled antibodies in vivo: assessment of tumor imaging using Cy3, Cy5, Cy5.5, and Cy7. Cancer Detect. Prevent. 22:1998;251-257.
13. Mujumdar S.R., Mujumdar R.B., Grant C.M., Waggoner A.S. Cyanine-labeling reagents: sulfobenzindocyanine succinimidyl esters. Bioconjugate Chem. 7:1996;356-362.
14. Oswald B., Patsenker L., Duschl J., Szmacinski H., Wolfbeis O.S., Terpetschnig E. Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels. Bioconjugate Chem. 10:1999;925-931.
15. Lin Y., Weissleder R., Tung C.-H. Novel near-infrared cyanine fluorochromes: synthesis, properties, and bioconjugation. Bioconjugate Chem. 13:2002;605-610.
16. S. Morishima, Y. Inagaki, T. Ishida, Information recording medium and oxonol compound, 1999, Japanese Patent No. 11025505A2.
17. Y. Inagaki, S. Ono, K. Adachi, Pyrazolo(3,4-b)pyridine derivative, 1988, Japanese Patent No. 63301882A2.
18. C.D. DeBoer, S. Evans, Infrared absorbing oxonol dyes for dye-donor element used in laser-induced thermal dye transfer, 1993, European Patent No. 403934B1.
19. Cohen L.B., Salzberg B.M., Davila H.V., Ross W.N., Landowne D., Waggoner A.S., Wang C.H. Changes in axon fluorescence during activity: molecular probes of membrane potential. J. Membr. Biol. 19:1974;1-36.
20. Waggoner A. Optical probes of membrane potential. J. Membr. Biol. 27:1976;217-334.
21. Plasek J., Sigler K. Slow fluorescent indicators of membrane potential: a survey of different approaches to probe response analysis. J. Photochem. Photobiol. B. 33:1996;101-124.
22. Smith J.C., Russ P., Cooperman B.S., Chance B. Synthesis, structure determination, spectral properties, and energy-linked spectral responses of the extrinsic probe oxonol V in membranes. Biochemistry. 15:1976;5094-5105.
23. Bashford C.L., Chance B., Smith J.C., Yoshida T. The behaviour of oxonol dyes in phospholipid dispersions. Biophys. J. 25:1979;63-85.
24. Epps D.E., Wolfe M.L., Groppi V. Characterization of the steady-state and dynamic fluorescence properties of the potential-sensitive dye bis-(1,3-dibutylbarbituric acid)trimethine oxonol (DiBAC4(3)) in model systems and cells. Chem. Phys. Lipids. 69:1994;137-150.
25. Benniston A.C., Harriman A., Gulliya K.S. Photophysical properties of merocyanine 540 derivatives. J. Chem. Soc. Faraday Trans. 90:1994;953-961.
26. Southwick P.L., Hahn K.M., Chao J., Perry P.L., Wagman A.S., Wagner M., Waggoner A.S. A long-wavelength biolabelling reagent based on the oxonol chromophore. J. Fluoresc. 5:1995;231-235.
27. R.Y. Tsien, J.E. Gonzalez III, Detection of transmembrane potentials by optical methods, 2000, US Patent No. 6,107,066.
28. Klonis N., Wang H., Quazi N.H., Casey J.L., Neumann G.M., Hewish D.R., Hughes A.B., Deady L.W., Tilley L. Characterization of a series of far red absorbing perylene diones: a new class of fluorescent probes for biological applications. J. Fluoresc. 11:2001;1-11.
29. Meech S.R., Phillips D. Photophysics of some common fluorescence standards. J. Photochem. 23:1983;193-217.
30. Zouni A., Clarke R.J., Visser A.J.W.G., Visser N.V., Holzwarth J.F. Static and dynamic studies of the potential-sensitive membrane probe RH421 in dimyristoylphosphatidylcholine vesicles. Biochim. Biophys. Acta. 1153:1993;203-212.
31. Roth N.J.L., Craig A.C. Predicted observable fluorescent lifetimes of several cyanines. J. Phys. Chem. 78:1974;1154-1155.
32. West W., Pearce S. The dimeric state of cyanine dyes. J. Phys. Chem. 69:1965;1894-1903.
33. Waggoner A.S., Wang C.H., Tolles R.L. Mechanism of potential-dependent light absorption changes of lipid bilayer membranes in the presence of cyanine and oxonol dyes. J. Membr. Biol. 33:1977;109-140.
34. Tsien R.Y., Hladky S.B. A quantitative resolution of the spectra of a membrane potential indicator, diS-C3-(5), bound to cell components and to red blood cells. J. Membr. Biol. 38:1978;73-97.
35. Sims P.J., Waggoner A.S., Wang C.-H., Hoffman J.F. Studies on the mechanism by which cyanine dyes measure membrane potential in red blood cells and phosphatidylcholine vesicles. Biochemistry. 13:1974;3315-3330.
36. Ernst L.A., Gupta R.K., Mujumdar R.B., Waggoner A.S. Cyanine dye labeling reagents for sulfhydryl groups. Cytometry. 10:1989;3-10.
37. Shealy D.B., Lipowska M., Lipowski J., Narayanan N., Sutter S., Strekowski L., Patonay P. Spectral characterization and evaluation of modified near-infrared laser dyes for DNA sequencing. Anal. Chem. 67:1995;247-251.
38. Feldman L.H., Herz A.H., Regan T.H. pH dependence of electronic and nuclear magnetic resonance spectra of isomeric cyanine dyes. J. Phys. Chem. 72:1968;2008-2013.
39. Dynes P.J., Chapman G.S., Kebede E., Schneider F.W. Kinetics of proton transfer to cyanines: temperature-jump study. J. Am. Chem. Soc. 94:1972;6356-6363.
40. Herz A.H. Protonation equilibriums of cyanines in solution and at silver bromide surfaces. Photogr. Sci. Eng. 18:1974;207-215.
41. Crockett A.O., Wittwer C.T. Fluorescein-labeled oligonucleotides for real-time PCR: using the inherent quenching of deoxyguanosine nucleotides. Anal. Biochem. 290:2001;89-97.
42. Kurata S., Kanagawa T., Yamada K., Torimura M., Yokomaku T., Kamagata Y., Kurane R. Fluorescent quenching-based quantitative detection of specific DNA/RNA using a BODIPY((R)) FL-labeled probe or primer. Nucleic Acids Res. 29:2001;E34.