Synthesis and effect of heterocycle modification on the spectroscopic properties of a series of unsymmetrical trimethine cyanine dyes

Dyes and Pigments

Volumn 105, Issue , 2014, Pages 238-249

  Levitz, Andrew ^a   Ladani, Safieh Tork ^a   Hamelberg, Donald ^a,b   Henary, Maged ^a,b  

^a GEORGIA STATE UNIVERSITY   (United States)

^b Center for Diagnostics and Therapeutics   (United States)

Author keywords

Cyanine dye; DFT calculation; Optical properties; Synthesis; Trimethine; Unsymmetrical

Indexed keywords

CYANINE DYES; DFT CALCULATION; ELECTRON-WITHDRAWING SUBSTITUENTS; SPECTROSCOPIC PROPERTY; SPECTROSCOPIC TECHNIQUE; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TRIMETHINE; UNSYMMETRICAL;

DENSITY FUNCTIONAL THEORY; OPTICAL PROPERTIES; SYNTHESIS (CHEMICAL);

STEEL BEAMS AND GIRDERS;

EID: 84896757044     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.02.009     Document Type: Article

References (40)

1. H. Wyler Die Betalaine Chemie unserer Zeit 3 5 1969 146 151
2. H. Wyler Das Experiment: Papierelektrophorese Chemie unserer Zeit 3 4 1969 111 115
3. H. Musso The pigments of fly agaric, Amanita muscaria Tetrahedron 35 24 1979 2843 2853
4. C. Reichardt Chiral polymethine dyes: a remarkable but forgotten conjugated pi system J Phys Org Chem 8 12 1995 761 773
5. F.M. Hamer The cyanine dyes and related compounds 1964 Interscience Publishers New York
6. S. Dähne, U. Resch-Genger, O.S. Wolfbeis, and North Atlantic Treaty Organization. Scientific Affairs Division Near-infrared dyes for high technology applications 1998 Kluwer Dordrecht; Boston
7. Y.F. Xu, Y. Liu, and X.H. Qian Novel cyanine dyes as fluorescent pH sensors: PET, ICT mechanism or resonance effect? J Photochem Photobiol A 190 1 2007 1 8
8. H.S. Choi, K. Nasr, S. Alyabyev, D. Feith, J.H. Lee, and S.H. Kim et al. Synthesis and in vivo fate of zwitterionic near-infrared fluorophores Angew Chem Int Ed 50 28 2011 6258 6263
9. H.S. Choi, S.L. Gibbs, J.H. Lee, S.H. Kim, Y. Ashitate, and F.B. Liu et al. Targeted zwitterionic near-infrared fluorophores for improved optical imaging Nat Biotechnol 31 2 2013 148 153
10. K. Licha, B. Riefke, V. Ntziachristos, A. Becker, B. Chance, and W. Semmler Hydrophilic cyanine dyes as contrast agents for near-infrared tumor imaging: synthesis, photophysical properties and spectroscopic in vivo characterization Photochem Photobiol 72 3 2000 392 398
11. S. Achilefu, R.B. Dorshow, J.E. Bugaj, and R. Rajagopalan Novel receptor-targeted fluorescent contrast agents for in vivo tumor imaging Invest Radiol 35 8 2000 479 485
12. H. Nakazumi Organic colorants for laser disc optical data storage J Soc Dye Colour 104 3 2008 121 125
13. I.M. Warner, S.A. Soper, and L.B. McGown Molecular fluorescence, phosphorescence, and chemiluminescence spectrometry Anal Chem 68 12 1996 R73 R91
14. R.P. Haugland, M.T.Z. Spence, and I.D. Johnson Handbook of fluorescent probes and research chemicals 6th ed. 1996 Molecular Probes Eugene, OR, USA (4849 Pitchford Ave., Eugene 97402)
15. T.G. Deligeorgiev, D.A. Zaneva, S.H. Kim, and R.W. Sabnis Preparation of monomethine cyanine dyes for nucleic acid detection Dyes Pigments 37 3 1998 205 211
16. L.G.S. Brooker, G.H. Keyes, and W.W. Williams Color and constitution. V.1 the absorption of unsymmetrical cyanines. Resonance as a basis for a classification of dyes J Am Chem Soc 64 2 1942 199 210
17. G. Beckford, E. Owens, M. Henary, and G. Patonay The solvatochromic effects of side chain substitution on the binding interaction of novel tricarbocyanine dyes with human serum albumin Talanta 92 2012 45 52
18. J.T. Goodwin, R.A. Conradi, N.F.H. Ho, and P.S. Burton Physicochemical determinants of passive membrane permeability: role of solute hydrogen-bonding potential and volume J Med Chem 44 22 2001 3721 3729
19. A.K. Ghose, V.N. Viswanadhan, and J.J. Wendoloski A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases J Comb Chem 1 1 1999 55 68
20. Q.Q. Shi, R. Sun, J.F. Ge, Q.F. Xu, N.J. Li, and J.M. Lu A comparative study of symmetrical and unsymmetrical trimethine cyanine dyes bearing benzoxazolyl and benzothiazolyl groups Dyes Pigments 93 1-3 2012 1506 1511
21. T. Zimmermann, and L. Hennig Ring transformations of heterocyclic compounds. XXII. Pyrido[1,2-a]indolium salts from 2-methyl-3H-indoles by pyrylium mediated three carbon annelation J Heterocycl Chem 39 2 2002 263 269
22. R. Nanjunda, E.A. Owens, L. Mickelson, S. Alyabyev, N. Kilpatrick, and S.M. Wang et al. Halogenated pentamethine cyanine dyes exhibiting high fidelity for G-quadruplex DNA Bioorg Med Chem 20 24 2012 7002 7011
23. B. Tang, L. Zhang, and K.H. Xu FIA-near-infrared spectrofluorimetric trace determination of hydrogen peroxide using tricarchlorobocyanine dye (Cy.7.Cl) and horseradish peroxidase (HRP) Talanta 68 3 2006 876 882
24. S.H. Sinha, E.A. Owens, Y. Feng, Y. Yang, Y. Xie, and Y. Tu et al. Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents Eur J Med Chem 54 2012 647 659
25. J.F. Xiang, Y.X. Liu, D. Sun, S.J. Zhang, Y.L. Fu, and X.H. Zhang et al. Synthesis, spectral properties of rhodanine complex merocyanine dyes as well as their effect on K562 leukemia cells Dyes Pigments 93 1-3 2012 1481 1487
26. P.J. Nigrey, and A.F. Garito Synthesis and characterization of 3-alkylbenzothiazolium salts J Chem Eng Data 22 4 1977 451 452
27. V.N. Viswanadhan, A.K. Ghose, G.R. Revankar, and R.K. Robins Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics J Chem Inf Comput Sci 29 3 1989 163 172
28. G. Klopman, J.-Y. Li, S. Wang, and M. Dimayuga Computer automated log P calculations based on an extended group contribution approach J Chem Inf Comput Sci 34 4 1994 752 781
29. H. Illy, and L. Funderburk Fischer indole synthesis. Direction of cyclization of isopropylmethyl ketone phenylhydrazone J Org Chem 33 11 1968 4283 4285
30. L. Yuan, W. Lin, and J. Song Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform Chem Commun (Camb) 46 42 2010 7930 7932
31. F.J. Evans, G.G. Lyle, J. Watkins, and R.E. Lyle Molecular rearrangements. VIII. The equilibration of 3,3-dimethyl-2-phenyl- and 2,3-dimethyl-3-phenyl-3H-indoles1 J Org Chem 27 5 1962 1553 1557
32. M. Le Romancer, I. Treilleux, K. Bouchekioua-Bouzaghou, S. Sentis, and L. Corbo Methylation, a key step for nongenomic estrogen signaling in breast tumors Steroids 75 8-9 2010 560 564
33. H. Lee, M.Y. Berezin, M. Henary, L. Strekowski, and S. Achilefu Fluorescence lifetime properties of near-infrared cyanine dyes in relation to their structures J Photochem Photobiol A Chem 200 2-3 2008 438 444
34. J. Wang, W.F. Cao, J.H. Su, H. Tian, Y.H. Huang, and Z.R. Sun Syntheses and nonlinear absorption of novel unsymmetrical cyanines Dyes Pigments 57 2 2003 171 179
35. S. Murphy, X.Q. Yang, and G.B. Schuster Cyanine borate salts that form penetrated ion-pairs in benzene solution - synthesis, properties, and structure J Org Chem 60 8 1995 2411 2422
36. F.A. Mikhailenko, N.P. Vasilenko, A.D. Kachkovskii, and R.I. Rozhinskii Effect of polar substituents and polymethine chain length on the color of cyanine dyes of the benz[c,d]indole series Zh Org Khim+ 18 1982 435 441
37. T.L. Branscombe, A. Frankel, J.H. Lee, J.R. Cook, Z. Yang, and S. Pestka et al. PRMT5 (Janus kinase-binding protein 1) catalyzes the formation of symmetric dimethylarginine residues in proteins J Biol Chem 276 35 2001 32971 32976
38. J.H. Flanagan, C.V. Owens, S.E. Romero, E. Waddell, S.H. Kahn, and R.P. Hammer et al. Near-infrared heavy-atom-modified fluorescent dyes for base-calling in DNA-sequencing applications using temporal discrimination Anal Chem 70 13 1998 2676 2684
39. F.M. Bickelhaupt, and E.J. Baerends Kohn-sham density functional theory: predicting and understanding chemistry. Reviews in computational chemistry 2007 John Wiley & Sons, Inc. 1 86
40. B. Champagne, M. Guillaume, and F. Zutterman TDDFT investigation of the optical properties of cyanine dyes Chem Phys Lett 425 1-3 2006 105 109