Long-wavelength absorbing and fluorescent chameleon labels for proteins, peptides, and amines

Bioconjugate Chemistry

Volumn 22, Issue 7, 2011, Pages 1433-1437

  Gorris, Hans H ^a   Saleh, Sayed M ^a   Groegel, Dominik B M ^a   Ernst, Steffen ^b   Reiner, Knut ^b   Mustroph, Heinz ^b   Wolfbeis, Otto S ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b FEW Chemicals   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; FLUORESCENCE; INFRARED DEVICES; PROTEINS;

BIOLOGICAL SAMPLES; COLOR CHANGES; CYANINE DYES; LABELINGS; LONG WAVELENGTH; NEAR INFRARED LIGHT; NUCLEOPHILIC SUBSTITUTIONS; PRIMARY AMINES; PROTEINS PEPTIDES; STRUCTURAL SIMILARITY;

AMINES;

AMINE; CYANINE DYE; FLUORESCENT DYE;

ARTICLE; CHEMICAL LABELING; CHEMICAL REACTION; COLOR; FLUORESCENCE; INFRARED RADIATION; PROTEIN ANALYSIS; PURIFICATION; SPECTROMETRY;

EID: 79960589201     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200192k     Document Type: Article

References (29)

1. Wetzl, B. K., Yarmoluk, S. M., Craig, D. B., and Wolfbeis, O. S. (2004) Chameleon labels for staining and quantifying proteins Angew. Chem., Int. Ed. 43, 5400-5402 (Pubitemid 39433932)
2. Craig, D. B., Wetzl, B. K., Duerkop, A., and Wolfbeis, O. S. (2005) Determination of picomolar concentrations of proteins using novel amino reactive chameleon labels and capillary electrophoresis laser-induced fluorescence detection Electrophoresis 26, 2208-2213 (Pubitemid 40852653)
3. Hoefelschweiger, B. K., Duerkop, A., and Wolfbeis, O. S. (2005) Novel type of general protein assay using a chromogenic and fluorogenic amine-reactive probe Anal. Biochem. 344, 122-129 (Pubitemid 41569385)
4. Schneider, E., Keller, M., Brennauer, A., Hoefelschweiger, B. K., Gross, D., Wolfbeis, O. S., Bernhardt, G., and Buschauer, A. (2007) Synthesis and characterization of the first fluorescent nonpeptide NPYY1 receptor antagonist ChemBioChem 8, 1981-1988
5. Meier, R. J., Steiner, M. S., Duerkop, A., and Wolfbeis, O. S. (2008) SDS-PAGE of proteins using a chameleon-type of fluorescent prestain Anal. Chem. 80, 6274-6279
6. Wojcik, R., Swearingen, K. E., Dickerson, J. A., Turner, E. H., Ramsay, L. M., and Dovichi, N. J. (2008) Reaction of fluorogenic reagents with proteins-I. Mass spectrometric characterization of the reaction with 3-(2-furoyl)quinoline-2-carboxaldehyde, Chromeo P465, and Chromeo P503 J. Chromatogr., A 1194, 243-248
7. Ramsay, L. M., Dickerson, J. A., Dada, O., and Dovichi, N. J. (2009) Femtomolar concentration detection limit and zeptomole mass detection limit for protein separation by capillary isoelectric focusing and laser-induced fluorescence detection Anal. Chem. 81, 1741-1746
8. Steiner, M. S., Meier, R. J., Spangler, C., Duerkop, A., and Wolfbeis, O. S. (2009) Determination of biogenic amines by capillary electrophoresis using a chameleon type of fluorescent stain Microchim. Acta 167, 259-266
9. Cohen, D., Dickerson, J. A., Whitmore, C. D., Turner, E. H., Palcic, M. M., Hindsgaul, O., and Dovichi, N. J. (2008) Chemical cytometry: Fluorescence-based single-cell analysis Annu. Rev. Anal. Chem. 1, 165-190
10. Hoffmann, K., Mix, R., Resch-Genger, U., and Friedrich, J. F. (2007) Monitoring of amino functionalities on plasma-chemically modified polypropylene supports with a chromogenic and fluorogenic pyrylium reporter Langmuir 23, 8411-8416 (Pubitemid 47237832)
11. Steiner, M. S., Meier, R. J., Duerkop, A., and Wolfbeis, O. S. (2010) Chromogenic sensing of biogenic amines using a chameleon probe and the red-green-blue readout of digital camera images Anal. Chem. 82, 8402-8405
12. Garcia-Acosta, B., Comes, M., Bricks, J. L., Kudinova, M. A., Kurdyukov, V. V., Tolmachev, A. I., Descalzo, A. B., Marcos, M. D., Martinez-Manez, R., Moreno, A., Sancenon, F., Soto, J., Villaescusa, L. A., Rurack, K., Barat, J. M., Escriche, I., and Amoros, P. (2006) Sensory hybrid host materials for the selective chromo-fluorogenic detection of biogenic amines Chem. Commun. 2239-2241 (Pubitemid 43800885)
13. Kostenko, O. M., Kovalska, V. B., Volkova, K. D., Shaytanov, P., Kocheshev, I. O., Slominskiy, Y. L., Pisareva, I. V., and Yarmoluk, S. M. (2006) New method for covalent fluorescent biomolecule labeling with hemicyanine dye J. Fluoresc. 16, 589-593 (Pubitemid 44048534)
14. Miller, J. N. (2008) Long-wavelength and near-infrared fluorescence: State of the Art, Future applications, and Standards, Springer, Berlin.
15. Oswald, B., Patsenker, L., Duschl, J., Szmacinski, H., Wolfbeis, O. S., 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
16. 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
17. Pham, W., Lai, W. F., Weissleder, R., and Tung, C. H. (2003) High efficiency synthesis of a bioconjugatable near-infrared fluorochrome Bioconjugate Chem. 14, 1048-1051 (Pubitemid 37152967)
18. Patonay, G., Salon, J., Sowell, J., and Strekowski, L. (2004) Noncovalent labeling of biomolecules with red and near-infrared dyes Molecules 9, 40-49 (Pubitemid 38982439)
19. Kele, P., Li, X. H., Link, M., Nagy, K., Herner, A., Lorincz, K., Beni, S., and Wolfbeis, O. S. (2009) Clickable fluorophores for biological labeling-with or without copper Org. Biomol. Chem. 7, 3486-3490
20. Li, X. H., Shi, W., Chen, S. M., Jia, J., Ma, H. M., and Wolfbeis, O. S. (2010) A near-infrared fluorescent probe for monitoring tyrosinase activity Chem. Commun. 46, 2560-2562
21. Zollinger, H. (2003) Color chemistry, synthesis properties, and applications of organic dyes and pigments, 3 rd ed., Wiley-VCH, Weinheim, Germany.
22. Ghosh, P. B. and Whitehou, Mw. (1968) 7-chloro-4-nitrobenzo-2-oxa-1,3- diazole - A new fluorigenic reagent for amino acids and other amines Biochem. J. 108, 155-156
23. Thorley, K. J., Hales, J. M., Anderson, H. L., and Perry, J. W. (2008) Porphyrin dimer carbocations with strong near infrared absorption and third-order optical nonlinearity Angew. Chem., Int. Ed. 47, 7095-7098
24. Reichardt, C. (1995) Chiral polymethine dyes: A remarkable but forgotten conjugated pi system J. Phys. Org. Chem. 8, 761-773
25. Landsman, M. L. J., Kwant, G., Mook, G. A., and Zijlstra, W. G. (1976) Light-absorbing properties, stability, and spectral stabilization of indocyanine green J. Appl. Physiol. 40, 575-583
26. Gorris, H. H., Ali, R., Saleh, S. M., and Wolfbeis, O. S. (2011) Tuning the dual emission of photon-upconverting nanoparticles for ratiometric multiplexed encoding Adv. Mater. 23, 1652-1655
27. Brown, H. C., Rao, C. G., and Ravindranathan, M. (1978) Structural effects in solvolytic reactions 0.29. Solvolysis of tertiary allylic para-nitrobenzoates-Effect of allylic double-bond on rates of solvolysis of representative tertiary para-nitrobenzoates J. Org. Chem. 43, 4939-4943
28. Schleyer, P. V., Bentley, T. W., Koch, W., Kos, A. J., and Schwarz, H. (1987) Structures and energies of isomeric cyclopentenyl cations. Resolution of the question of anchimeric assistance in cyclopenten-4-yl solvolysis J. Am. Chem. Soc. 109, 6953-6957
29. Sorensen, T. S. (1969) The equilibria and kinetics of the cyclohexenyl-cyclopentenyl cation rearrangement J. Am. Chem. Soc. 91, 6398-6403