Protolytic fluorescein species evaluated using chemometry and DFT studies

Dyes and Pigments

Volumn 86, Issue 1, 2010, Pages 15-24

  Batistela, Vagner Roberto ^a   da Costa Cedran, Jaime ^a   Moisés de Oliveira, Hueder Paulo ^b   Scarminio, Ieda Spacino ^c   Ueno, Leonardo Tsuyoshi ^d   Eduardo da Hora Machado, Antonio ^e   Hioka, Noboru ^a  

^a STATE UNIVERSITY OF MARINGÁ   (Brazil)

^b UNIVERSIDADE CAMILO CASTELO BRANCO   (Brazil)

^c STATE UNIVERSITY OF LONDRINA   (Brazil)

^d FEDERAL UNIVERSITY OF UBERLÂNDIA   (Brazil)

^e FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Chemometry; Density functional theory; Fluorescein; pKa; Principal component analysis; Xanthene

Indexed keywords

ACID BASE; CHEMOMETRIC TOOLS; CHEMOMETRICS; CHEMOMETRY; DFT STUDY; ELECTRONIC ABSORPTION SPECTRA; ELECTRONIC TRANSITION; GEOMETRIC PARAMETER; MONOANIONS; POLARIZED CONTINUUM MODELS; PRINCIPAL COMPONENTS; PROTOLYTIC EQUILIBRIA; Q-FACTORS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; WATER MOLECULE;

CONTINUUM MECHANICS; DYES; PRINCIPAL COMPONENT ANALYSIS; WATER ANALYSIS;

DENSITY FUNCTIONAL THEORY;

ABSORPTION; ACID DYE; COLOR; COMPUTER SIMULATION; MATHEMATICAL MODEL; STATISTICAL ANALYSIS;

EID: 74449091957     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.11.002     Document Type: Article

References (62)

1. Tan W., Shi Z., and Kopelman Y. Development of submicron chemical fiber optic sensors. Analytical Chemistry 64 (1992) 2985-2990
2. Stirling R.V. Video techniques in neurobiology. Trends in Neurosciences 9 (1986) 145-147
3. 2+. Journal of the American Chemical Society 122 (2000) 5644-5645
4. Setsukinai S., Urano Y., Kakinuma K., Majima H.J., and Nagano T. Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species. Journal of Biological Chemistry 278 (2003) 3170-3175
5. McIntyre D. The stimulation of fluorescein in external ophthalmic photography. Journal of the Biological Association 35 4 (1967) 155-157
6. Tripathi R.C., Millard C.B., and Tripathi B. Protein composition of human aqueous humor: SDS-PAGE analysis of surgical and post-mortem samples. Experimental Eye Research 48 1 (1989) 117-130
7. Masereeuw R., Bergh E., Bindels R.J., and Russel F.G.M. Characterization of fluorescein transport in isolated proximal tubular cells of the rat: evidence for mitochondrial accumulation. Journal of Pharmacology and Experimental Therapeutics 269 (1994) 1261-1267
8. Kojima H., Nakatsubo N., Kikuchi K., Kawara S., Kirino Y., Nagoshi H., et al. Detection and imaging of nitric oxide with novel fluorescent indicators: diaminofluoresceins. Analytical Chemistry 70 (1998) 2446-2453
9. Slavik J. Fluorescent probes in cellular and molecular biology (1994), CRC Press, Florida
10. Sjöback R., Nygren J., and Kubista M. Absorption and fluorescence properties of fluorescein. Spectrochimica Acta A: Molecular Biomolecular Spectroscopy 51 (1995) L7-L21
11. Klonis N., and Sawyer W.H. Spectral properties of the prototropic forms of fluorescein in aqueous solutions. Journal of Fluorescence 6 (1996) 147-157
12. Leonhardt H., Gordon L., and Livingston R. Acid-base equilibria of fluorescein and 2′7′-dichlorofluorescein in their ground and fluorescent states. Journal of Physical Chemistry 76 1 (1971) 245-249
13. Mchedlov-Petrossyan N.O., Bryleva E.Y., Vodalazkaya N.A., Dissanayake A.A., and Ford W.T. Nature of cationic poly(propylenimine) dendrimers in aqueous solutions using versatile indicator dyes. Langmuir 24 (2008) 5689-5699
14. Anthoni U., Christophersen C., Nielsen P.H., Püschl A., and Schaumburg K. Structure of red and orange fluorescein. Structural Chemistry 6 3 (1995) 161-165
15. Markuszewski R., and Diehl H. The infrared spectra and structures of three solid forms of fluorescein and related compounds. Talanta 27 (1980) 937-946
16. 2O-DMSO mixtures. Journal of the Chemical Society, Faraday Transactions 88 20 (1992) 3025-3032
17. Albert A., and Serjeant E.P. The determination of ionization constants. A laboratory manual. 2nd ed. (1971), Chapman and Hall Ltd, London p. 53
18. Lang K., Mosinger J., and Wagnerová D.M. Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules; models for photodynamic therapy. Coordination Chemistry Reviews 248 (2004) 321-350
19. Sena M.M., Scarminio I.S., Collins K.E., and Collins C.H. Speciation of aqueous chromium(VI) solutions with the aid of Q-mode factor analysis followed by oblique projection. Talanta 53 (2000) 453-461
20. Gholivand M.B., Ghasemi J.B., Saaidpour S., and Mohajeri A. Spectrophotometric study of the effects of surfactants and ethanol on the acidity constants of fluorescein. Spectrochimica Acta Part A 71 (2008) 1158-1165
21. Tamulis A., Tamuliene J., Balevicius M.L., Rinkevicious Z., and Tamulis V. Quantum mechanical studies of intensity in electronic spectra of fluorescein dianion and monoanion forms. Structural Chemistry 14 6 (2003) 643-648
22. Hirano K. Electronic structure and spectra of organic dye anions of uranine and eosin Y. Bulletin of the Chemical Society of Japan 56 (1983) 850-854
23. Jang Y.H., Hwang S., and Chung D.S. Tautomeric equilibrium of fluorescein in solution: ab initio calculations. Chemistry Letters 2 (2001) 1316-1317
24. Fabian W.M., Schuppler S., and Wolfbeis O.S. Effects of annulation on absorption and fluorescence characteristics of fluorescein derivatives: a computational study. Journal of the Chemical Society, Perkin Transactions 2 29 (1996) 853-856
25. Acemioǧlu B., Arik M., Efeoǧlu H., and Onganer Y. Solvent effect on the ground and excited state dipole moments of fluorescein. Journal of Molecular Structure (Theochem) 548 (2001) 165-171
26. Wang L., Roitberg A., Meuse C., and Gaigalas A.K. Raman and FTIR spectroscopies of fluorescein in solutions. Spectrochimica Acta A: Molecular Biomolecular Spectroscopy 57 (2001) 1781-1791
27. Krol M., Wrona M., Page C.S., and Bates P.A. Macroscopic pKa calculations for fluorescein and its derivatives. Journal of Chemical Theory and Computation 2 6 (2006) 1520-1529
28. Mchedlov-Petrossyan N.O., and Ivanov V.V. Effect of the solvent on the absorption spectra and protonation of fluorescein dye anions. Russian Journal of Physical Chemistry A 81 1 (2007) 112-115
29. Previdello B.A.F., Carvalho F.R., Tessaro A.L., Souza V.R., and Hioka N. O pKa de indicadores ácido-base e os efeitos de sistemas coloidais. Química Nova 29 3 (2006) 600-606
30. Março P.H., and Scarminio I.S. Q-mode curve resolution of UV-Vis spectra for structural transformation studies of anthocyanins in acidic solutions. Analytica Chimica Acta 583 (2007) 138-146
31. Onsager L. Electric moments of molecules in liquids. Journal of the American Chemical Society 58 (1936) 1486-1493
32. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 03, revision C.02 (2004), Gaussian, Inc, Wallingford, CT
33. Ochterski JW. In: Thermochemistry in Gaussian, http://www.gaussian.com/g_whitepap/thermo.htm, [accessed 22.03.09].
34. Runge E., and Gross E.K.U. Density-functional theory for time-dependent systems. Physical Review Letters 52 (1984) 997-1000
35. Casida M.E., Jamorski C., Casida K.C., and Salahub D.R. Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: characterization and correction of the time-dependent local density approximation ionization threshold. Journal of the Chemical Physics 108 (1998) 4439-4449
36. Cancès E., Mennucci B., and Tomasi J. A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. Journal of the Chemical Physics 107 (1997) 3032-3041
37. Tomasi J., Mennucci B., and Cammi R. Quantum mechanical continuum solvation models. Chemical Reviews 105 (2005) 2999-3094
38. Flükiger P., Lüthi H.P., Portmann S., and Weber J. Molekel 4.3 (2000-2002), Swiss Center for Scientic Computing, Switzerland
39. Portmann S., and Lüthi H.P. MOLEKEL: an interactive molecular graphics tool. Chimia 54 (2000) 766-770
40. Espenson J.H. Chemical kinetics and reactions mechanism. 1st ed. (1981), McGraw-Hill, New York p. 117
41. Reyment R.A., Jöreskog K.G., and Klovan J.E. Geological factor analysis (1976), Elsevier, Amsterdam
42. Davis J.C. Statistics and data analysis in geology. 3rd ed. (2002), John Wiley & Sons, New York
43. Forina M., Armanino C., Lanteri S., and Leardi R. Methods of varimax rotation in factor analysis with applications in clinical and food chemistry. Journal of Chemometrics 3 (1988) 115-125
44. Miesch A.T. Q-mode factor analysis of compositional data. Computers and Geosciences 1 (1976) 147-159
45. Kubista M., Sjöback R., and Albinson B. Determination of equilibrium constants by chemometric analysis of spectroscopic data. Analytical Chemistry 65 8 (1993) 994-998
46. Kubista M., Sjöback R., and Nygren J. Quantitative spectral analysis of multicomponent equilibria. Analytica Chimica Acta 302 (1995) 121-125
47. Chowdhary R.K., Chansarkar N., Sharif I., Hioka N., and Dolphin D. Formulations of benzoporphyrin derivatives in pluronics. Photochemistry Photobiology 77 3 (2003) 299-303
48. Simplicio F.I., Soares R.R.S., Maionchi F., Santin Filho O., and Hioka N. Aggregation of a benzoporphyrin derivative in water/organic solvent mixtures: a mechanistic Proposition. Journal of Physical Chemistry A 108 (2004) 9384-9389
49. Tessaro A.L., Fernandes D.M., Terezo A.J., Souza V.R., and Hioka N. Influences of experimental parameters on the stability of a benzoporphyrin drug in water/ethanol mixtures: a statistical approach investigation. Journal of Porphyrins and Phthalocyanines 9 (2005) 609-616
50. Skoog D.A., West D.M., and Holler F.J. Fundamentals of analytical chemistry. 6th ed. (1992), Saunders College Pub, Fort Worth
51. Briggs A.J., Glenn R., Jones P.G., Kirby A.J., and Ramaswamy P. Bond length and reactivity. Stereoelectronic effects on bonding in acetals and glucosides. Journal of the American Chemical Society 106 (1984) 6200-6206
52. 1H NMR and quantum chemical calculations. Bioorganic and Medicinal Chemistry Letters 4 10 (1996) 1783-1794
53. Neckers D.C. The Indian happiness wart in the development of photodynamic action. Journal of Chemical Education 64 8 (1987) 649-656
54. Wang X., Song M., and Long Y. Synthesis, characterization, and crystal structure of the lactone form of rhodamine B. Journal of Solid State Chemistry 156 (2001) 325-330
55. Samoilov D.V., Mchedlov-Petrosyan N.O., Martynova V.P., and El'tsov A.V. Protolytic equilibria of fluorescein nitro derivatives. Russian Journal of General Chemistry 70 8 (2000) 1343-1357
56. Mchedlov-Petrossyan N.O., and Kleshchevnikova V.N. Influence of the cetyltrimethylammonium chloride micellar pseudophase on the protolytic equilibria of oxyxanthene dyes at high bulk phase ionic strength. Journal of the Chemical Society, Faraday Transactions 90 4 (1994) 629-640
57. Lide D.R. CRC handbook of physics and chemistry. 85th ed. (2005), CRC Press, New York
58. Wang L., Roitberg A., Meuse C., and Gaigalas A.K. Raman and FTIR spectroscopies of fluorescein in solutions. Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy 57 (2001) 1781-1791
59. Osborn S., and Rogens D. The crystal and molecular structure of the 1:1 complex of acetone with the lactoid form of fluorescein. Acta Crystallographica B 31 (1975) 359-364
60. Miura T., Urano Y., Tanaka K., Nagano T., Ohkubo K., and Fukuzumi S. Rational design principle for modulating fluorescence properties of fluorescein-based probes by photoinduced electron transfer. Journal of the American Chemical Society 125 (2003) 8666-8671
61. Ueno T., Urano Y., Setsukinai K., Takakusa H., Kojima H., Kikuchi K., et al. Rational principles for modulating fluorescence properties of fluorescein. Journal of the American Chemical Society 126 (2004) 14079-14085
62. Belletête M., Wakim S., Leclerc M., and Durocher G. Emission energies and photophysical properties of ladder oligo(p-aniline)s. Journal of Molecular Structure (Theochem) 760 (2006) 147-152