Simple one-pot preparation of water-soluble, cysteine-reactive cyanine and merocyanine dyes for biological imaging

Bioconjugate Chemistry

Volumn 18, Issue 4, 2007, Pages 1344-1348

  Toutchkine, Alexei ^a,b   Nguyen, Dan Vinh ^a   Hahn, Klaus M ^a  

^a UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^b Sigma Aldrich Co   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROPHORES; PROTEINS;

BIOLOGICAL IMAGING; CYANINE DYES; MEROCYANINE DYE; ONE-POT PREPARATIONS; ONE-POT PROCEDURES; SIDE-CHAINS; SIMPLE++; SULPHONATES; TRIMETHYL; WATERSOLUBLE;

AMINO ACIDS;

1 (3 AMMONIOPROPYL) 2,3,3 TRIMETHYL 3H INDOLIUM 5 SULFONATE BROMIDE; AMMONIUM DERIVATIVE; CHLORINE DERIVATIVE; CYANINE DYE; CYSTEINE; INDOLE DERIVATIVE; IODOACETAMIDE; MEROCYANINE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; COMPLEX FORMATION; COVALENT BOND; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; IMAGING SYSTEM; QUANTUM YIELD; SYNTHESIS;

EID: 34547225529     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060376n     Document Type: Article

References (18)

1. Sturmer, D. M. (1977) Synthesis and properties of cyanine and related dyes. In Special topics in heterocyclic chemistry (Weissberger, A., and Taylor, E. C., Eds.) pp 441-587, John Wiley & Sons, New York.
2. Tani, T., Miyamoto, Y., Fujimori, K. E., Taguchi, T., Yanagida, T., Sako, Y., and Harada, Y. (2005) Trafficking of a ligand-receptor complex on the growth cones as an essential step for the uptake of nerve growth factor at the distal end of the axon: a single-molecule analysis. J. Neurosci. 25, 2181-91.
3. Borisenko, V., Lougheed, T., Hesse, J., Fureder-Kitzmuller, E., Fertig, N., Behrends, J. C., Woolley, G. A., and Schutz, G. J. (2003) Simultaneous optical and electrical recording of single gramicidin channels. Biophys. J. 84, 612-22.
4. Redkar, R. J., Schultz, N. A., Scheumann, V., Burzio, L. A., Haines, D. E., Metwalli, E., Becker, O., and Conzone, S. D. (2006) Signal and sensitivity enhancement through optical interference coating for DNA and protein microarray applications. J. Biomol. Technol. 17, 122-30.
5. Nalbant, P., Hodgson, L., Kraynov, V., Toutchkine, A., and Hahn, K. M. (2004) Activation of endogenous Cdc42 visualized in living cells. Science 305, 1615-9.
6. Toutchkine, A., Kraynov, V., and Hahn, K. (2003) Solvent-sensitive dyes to report protein conformational changes in living cells. J. Am. Chem. Soc. 125, 4132-45.
7. Gruber, H. J., Kada, G., Pragl, B., Riener, C., Hahn, C. D., Harms, G. S., Ahrer, W., Dax, T. G., Hohenthanner, K., and Knaus, H. G. (2000) Preparation of thiol-reactive Cy5 derivatives from commercial Cy5 succinimidyl ester. Bioconjugate Chem. 11, 161-6.
8. Ernst, L. A., Gupta, R. K., Mujumdar, R. B., and Waggoner, A. S. (1989) Cyanine dye labeling reagents for sulfhydryl groups. Cytometry 10, 3-10.
9. Toutchkine, A., Nalbant, P., and Hahn, K. M. (2002) Facile synthesis of thiol-reactive Cy3 and Cy5 derivatives with enhanced water solubility. Bioconjugate Chem. 13, 387-91.
10. Mason, S. J., Hake, J. L., Nairne, J., Cummins, W. J., and Balasubramanian, S. (2005) Solid-phase methods for the synthesis of cyanine dyes. J. Org. Chem. 70, 2939-2949.
11. Brooker, L. G. S., White, F. L., Keyes, G. H., Smyth, C. P., and Oesper, P. F. (1941) Color and constitution. II. Absorptions of some related vinylene-homologous series. J. Am. Chem. Soc. 63, 3192-203.
12. Onganer, Y., Yin, M., Bessire, D. R., and Quitevis, E. L. (1993) Dynamical solvation effects on the cis-trans isomerization reaction: photoisomerization of merocyanine 540 in polar solvents. J. Phys. Chem. 97, 2344-2354.
13. Demas, J. N., and Crosby, G. A. (1971) The Measurement of Photoluminescence Quantum Yields. A Review. J. Phys. Chem. 75, 991-1024.
14. Panchuk-Voloshina, N., Haugland, R. 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, 1179-88.
15. Mujumdar, S. R., Mujumdar, R. B., Grant, C. M., and Waggoner, A. S. (1996) Cyanine-Labeling Reagents: Sulfobenzindocyanine Succinimidyl Esters. Bioconjugate Chem. 7, 356-362.
16. Kamal, P. V., and Lichtin, N. N. (1981) Electron Transfer in the Quenching of Protonated Triplet Methylene Blue by Ground-State Molecules of the Dye. J. Phys. Chem. 85, 814-818.
17. Vaiana, A. C., Neuweiler, H., Shulz, A., Wolfrum, J., Sauer, M., and Smith, J. C. (2003) Fluorescence Quenching of Dyes by Tryptofan: Interactions of Atomic Detail from Combination of Experiment and Computer Stimulations. J. Am. Chem. Soc. 125, 14564-14572.
18. Polgar, L. (1973) On the Mode of Activation of the Catalitically Essential Sulfhydryl Group of Papain. Eur. J. Biochem. 33, 104-109.