Water soluble squaraine dyes for use as colorimetric stains in gel electrophoresis

Dyes and Pigments

Volumn 94, Issue 3, 2012, Pages 393-402

  Lynch, Daniel E ^a,b   Kirkham, Andrew N ^a   Chowdhury, Mohammed Z H ^a   Wane, Elizabeth S ^a   Heptinstall, John ^a  

^a Institute for Clean Growth and Future Mobility   (United Kingdom)

^b EXILICA LIMITED   (United Kingdom)

Author keywords

Colorimetric stain; Fluorescence; Gel electrophoresis; Protein detection; Squaraine dyes; X ray crystal structure

Indexed keywords

COLORIMETRIC STAIN; GEL ELECTROPHORESIS; PROTEIN DETECTION; SQUARAINE DYES; X RAY CRYSTAL STRUCTURES;

CATALYSTS; COLORIMETRY; DYES; ELECTROPHORESIS; FLUORESCENCE;

COLOR;

EID: 84858120015     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.02.001     Document Type: Article

References (38)

1. H.-E. Sprenger, and W. Ziegenbein The cyclobutenediylium cation, a novel chromophore from squaric acid Angew Chem Int Ed 6 1967 553 554
2. A.H. Schmidt Reaktionen von quadratsäure und quadratsäure- derivaten Synthesis 12 1980 961 994
3. J.J. McEwen, and K.J. Wallace Squaraine dyes in molecular recognition and self-assembly Chem Commun 2009 6339 6351
4. N. Kuramoto, K. Natsukawa, and K. Asao Synthesis and characterisation of deep-coloured squarylium dyes for laser optical recording media Dyes Pigm 11 1989 21 35
5. B. Zhang, W. Zhao, Y. Cao, X. Wang, Z. Zhang, and X. Jiang Photoluminescence and electroluminescence of squarylium cyanine dyes Synth Met 91 1997 237 241
6. G. Dilek, and E.U. Akkaya Novel squaraine signalling Zn(II) ions: three-state fluorescence response to a single input Tetrahedron Lett 41 2000 3721 3724
7. F. Meadows, N. Narayanan, and G. Patonay Determination of protein-dye association by near infrared fluorescence-detected circular dichroism Talanta 50 2000 1149 1155
8. D. Scherer, R. Dörfler, A. Feldner, T. Vogtmann, M. Schwoerer, and U. Lawrentz Two-photon states in squaraine monomers and oligomers Chem Phys 279 2002 179 207
9. G.-S. Jiao, A. Loudet, H.B. Lee, S. Kalinin, and LB-A. Johansson Syntheses and spectroscopic properties of energy transfer systems based on squaraines Tetrahedron 59 2003 3109 3116
10. Y. He, W. Zhou, F. Wu, M. Li, and E. Wang Photoreaction and photopolymerization studies on squaraine dyes/iodonium salts combination J Photochem Photobio A Chem 162 2004 463 471
11. K.P. Grytsenko, and S. Schrader Nanoclusters in polymer matrices prepared by co-deposition from a gas phase Adv Colloid Interface Sci 116 2005 263 276
12. Y. Kawabata, T. Sekiguchi, M. Tanaka, T. Nakamura, H. Komizu, and K. Honda Supermolecular structure in the Langmuir-Blodgett films of a surface-active dye-fatty acid mixed system J Am Chem Soc 107 1985 5270 5271
13. M. Matsumoto, T. Nakamura, M. Tanaka, T. Sekiguchi, H. Komizu, and S.Y. Matsuzaki Structure study of supermolecular layers in Langmuir-Blodgett films. Surface active squarylium dye-fatty acid binary mixed system Bull Chem Soc Jpn 60 1987 2737 2742
14. K.S. Mathis, M.G. Kuzyk, C.W. Dirk, A. Tan, S. Martinez, and G. Gampos Mechanisms of the nonlinear optical properties of squaraine dyes in poly(methyl methacrylate) polymer J Opt Soc Am B 15 1998 871 883
15. 13C-NMR of an indolenium squaraine dye Dyes Pigm 43 1999 67 71
16. U. Lawrentz, W. Grahn, I. Dix, and P.G. Jones 2,4-Bis{[6-(2,2- dimethylpropyl)-3-ethyl-1,3-benzothiazol-2(3H)-ylidene]methyl} cyclobutenediylium-1,3-diolate Acta Cryst C57 2001 126 128
17. D.E. Lynch 2,4-Bis(3,3-dimethyl-1-octylindolin-2-ylidenemethyl) cyclobutenediylio-1,3-diolate Acta Cryst E58 2002 o1025 o1027
18. O.P. Dimitriev Anomalous aggregation of squaraine dyes in confined solutions J Mol Liquids 120 2005 131 133
19. E. Terpetschnig, H. Szmacinski, and J.R. Lakowicz Synthesis, spectral properties and photostabilities of symmetrical and unsymmetrical squaraines; a new class of fluorophores with long-wavelength excitation and emission Anal Chim Acta 282 1993 633 641
20. E. Terpetschnig, and J.R. Lakowicz Synthesis and characterisation of unsymmetrical squaraines: a new class of cyanine dyes Dyes Pigm 21 1993 227 234
21. E. Terpetschnig, H. Szmacinski, A. Ozinskas, and J.R. Lakowicz Synthesis of squaraine-N-hydroxysuccinamide esters and their biological application as long-wavelength fluorescent labels Anal Biochem 217 1993 197 204
22. A.J.G. Mank, H.T.C. van der Laan, H. Lingeman, C. Gooijer, UATh Brinkman, and N.H. Velthorst Visible diode laser-induced fluorescence detection in liquid chromatography after precolumn derivatization of amines Anal Chem 67 1995 1742 1748
23. B. Kukrer, and E.U. Akkaya Red to IR fluorescent signalling of carbohydrates Tetrahedron Lett 40 1999 9125 9128
24. B. Oswald, L. Patsenker, J. Duschl, H. Szmacinski, O.S. Wolfbeis, and E. Terpetschnig Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels Bioconjug Chem 10 1999 925 931
25. B. Oswald, F. Lehmann, L. Simon, E. Terpetschnig, and O. Wolfbeis Red laser-induced fluorescence energy transfer in an immunosystem Anal Biochem 280 2000 272 277
26. N. Nizomov, Z.F. Ismailov, S.N. Nizamov, M.K. Salakhitdinova, A.L. Tatarets, and L.D. Patsenker Spectral-luminescent study of interaction of squaraine dyes with biological substances J Mol Struct 788 2006 36 42
27. A.L. Tatarets, I.A. Fedyunyayeva, T.S. Dyubko, Y.A. Povrozin, A.O. Doroshenko, and E.A. Terpetschnig Synthesis of water-soluble, ring-substituted squaraine dyes and their evaluation as fluorescent probes and labels Anal Chim Acta 570 2006 214 223
28. K.D. Volkova, V.B. Kovalska, A.L. Tatarets, L.D. Patsenker, D.V. Kryvorotenko, and S.M. Yarmoluk Spectroscopic study of squaraines as protein-sensitive fluorescent dyes Dyes Pigm 72 2007 285 292
29. Hamilton AL, West RM, Cummins WJ, Briggs MSJ, Bruce IE. Squaraine dyes and their use in fluorescent sequencing method. Patent 1997:US 6,140,494.
30. Singh R, Gorski G, Frenzel G. Bridged fluorescent dyes, their preparation and their use in assays. Patent 2000:US 6,403,807.
31. West RM, Cummins WJ, Nairne RJD, Bull MG. Squaraine dyes. Patent 2000:WO 00/58405.
32. Deroover G, Missfeldt M, Simon L. Use of acylsulfonamido-substituted polymethine dyes as fluorescence dyes and/or markers. Patent 2001:US 6,995,262.
33. Weaver GW, Smith A, Palmer DA, French MT. Long wavelength 4-[1-(naphtha[1,2-d]thiazol-1-ium-2-yl)methylidene]-3-oxo-2-[(2, 3-dihydro-1H-indol-2-yliden)methyl]cyclobuten-1-olate based fluorescent dyes. Patent 2001:GB 2,373,509.
34. U.K. Laemmli Cleavage of structural proteins during the assembly of the head of bacteriophage T4 Nature 227 1970 680 685
35. Y. Suzuki, and K. Yokoyama A protein-responsive chromophore based on squaraine and its application to visual protein detectionon a gel for SDS-PAGE Angew Chem Int Ed 46 2007 4097 4099
36. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the folin phenol reagent J Biol Chem 193 1951 265 275
37. E.E. Havinga, A. Pomp, W. Ten Hoeve, and H. Wynberg Water-soluble polysquaraines and polycroconaines Synth Met 69 1995 581 582
38. G.R. Desiraju Hydration in organic crystals: prediction from molecular structure J Chem Soc Chem Commun 1991 426 428