Synthesis and properties of phosphonic acid containing cyanine and squaraine dyes for use as fluorescent labels

Bioconjugate Chemistry

Volumn 18, Issue 6, 2007, Pages 2178-2190

  Reddington, Mark V ^a  

^a Biosearch Technologies Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE;

ABSORPTION PROPERTY; AROMATIC RESIDUES; CYANINE DYES; FLUORESCENCE PROPERTIES; FLUORESCENT LABELS; PHOSPHONATE GROUP; PHOSPHONIC ACIDS; PROPERTY; SQUARAINE DYES; SYNTHESISED;

OLIGONUCLEOTIDES;

CYANINE DYE 3; DYE; ESTER DERIVATIVE; FLUORESCENT DYE; OLIGONUCLEOTIDE; PHOSPHONIC ACID DERIVATIVE; PROTEIN; SQUARAINE DYE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; FLUORESCENCE; SYNTHESIS;

EID: 36848999914     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc070090y     Document Type: Article

References (22)

1. Haugland, R. P. (2002) Handbook of Fluorescent Probes and Research Products, 9th ed., Molecular Probes, Eugene, OR.
2. Tsien, R. Y. and Waggoner, A. S. (1995) Handbook of Biological Confocal Microscopy (Pawley, J. B., Ed.) Springer, New York.
3. Panchuk-Voloshine, N., Haugland Rosario, P., Bishop-Stewart, J., Bhalgat, M. K., Millard, P. J., Mao, F., Leung, W.-Y., and Haugland, R. P. (1999) Alexa dyes, a series of new fluorescent dyes that yield exceptionally bright, photostable conjugates. J. Histochem. Cytochem. 47, 1179-1188.
4. Mujumbdar, R. B., Earnst, L. A., Mujumbdar, S. R., Lewis, C. J., and Waggoner, A. S. (1993) Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters. Bioconjugate Chem. 4, 105-111.
5. Mujumbdar, S. R., Mujumbdar, R. B., Grant, C. M., and Waggoner, A. S. (1996) Cyanine dye labeling reagents: sulfobenzindocyanine succinimidyl esters. Bioconjugate Chem. 7, 356-362.
6. West, R. M., Bosworth, N., and Mujumbdar, R. B. (2005) Cyanine Dye Labeling Reagents. WO 2005/044,923.
7. Cummins, W., West, R., and Smith, J. A. (2002) Cyanine Dyes. U.S. Patent 6,348,599.
8. Reddington, M. V. (1998) New glycoconjugated cyanine dyes as fluorescent labeling reagents. J. Chem. Soc., Perkin Trans. 1, 143-147.
9. Gousou, C., Vasseur, J.-J., Bazin, H., Trinquet, E., Maurin, F., and Morvan, F. (2005) Optimized synthesis of functionalized fluorescent oligodeoxynucleotides for protein labeling. Bioconjugate Chem. 16, 465-470.
10. Devlin, R., Studholme, R. M., Dandliker, W. B., Fahy, E., Blumeyer, K., and Ghosh, S. S. (1993) Homogeneous detection of nucleic acids by transient-state polarized fluorescence. Clin. Chem. 39, 1939-1943.
11. Wolfbeis, O. S. (2001) Methods for Solubilizing Optical Markers. WO 01/36,973.
12. Borbas, K. E., Mroz, P., Hamblin, M., and Lindsey, J. S. (2006) Bioconjugatable porphyrins bearing a compact swallowtail motif for water solubility. Bioconjugate Chem. 17, 638-653.
13. Oswald, B., Gruber, M., Bohmer, M., Lehman, F., Probst, M., and Wolfbeis, O. S. (2001) Novel diode laser-compatible fluorophores and their application to single molecule detection, protein labeling and fluorescence resonance energy transfer immunoassay. Photochem. Photobiol. 74, 237-245.
14. Olmstead, J., III (1979) Calorimetric determinations of absolute fluorescence quantum yields. J. Phys. Chem. 83, 2581-2584.
15. Kawakami, M., and Kitaguchi, H. (2005) Cyanine Dyes. U.S. Patent 6,939,975.
16. Tavs, P. (1970) Reaction of aryl halides with trialkyl phosphites and dialkyl benzenephosphonites to aromatic phosphonates and phosphinates by nickel salt catalysed arylation. Chem. Ber. 103, 2428-2436.
17. Southwick, P. L., Earnst, L. A., Tauriello, E. W., Parker, S. R., Mujumbdar, R. B., Mujumbdar, S. R., Lewis, H. A., and Waggoner, A. S. (1990) Cyanine dye labeling reagents: carboxymethylindocyanine succinimidyl esters. Cytometry 11, 418-430.
18. Gale, D. J., Lin, J., and Wilshire, J. F. K. (1970) The amidomethylation of Fischer's base. The preparation of some new polymethine dyes. Aust. J. Chem. 30, 689-694.
19. Yee, K.-Y., Bailey, F. C., and Bluett, L. J. (1986) Squaraine chemistry. On the anomalous mass spectra of bis(4-dimethylaminophenyl)squaraine and its derivatives. Can. J. Chem. 64, 1607-1619.
20. Oswald, B., Patsenker, L., Duschl, J., Szmacinski, H., Wolfbeis, O., and Terpetschnig, E. (1999) Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels. Bioconjugate Chem. 10, 925-931.
21. Albert, A., and Sergent, E. P. (1962) Ionization Constants of Acids and Bases Wiley, New York.
22. Gruber, H. J., Hahn, C. D., Kada, G., Reiner, C. K., Harms, G. S., Ahrer, W., Dax, T. G., and Knaus, H.-G. (2000) Anomalous fluorescence enhancement of Cy3 and Cy3.5 versus anomalous fluorescence loss of Cy5 and Cy7 upon covalent linking to IgG and noncovalent binding to avidin. Bioconjugate Chem. 11, 696-704.