Study on the interaction of Basic Violet 2 with hydroxypropyl-β- cyclodextrin

Dyes and Pigments

Volumn 92, Issue 1, 2012, Pages 758-765

  Aiassa Martínez, Ivana M ^a   Montes De Oca, María N ^b   Iriarte, Ana G ^a   Ortiz, Cristina S ^b   Argüello, Gerardo A ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

^b UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

Association constant; Basic Violet 2; Cyclodextrin; Photosensitizer; Triarylmethanes; Visible spectroscopy

Indexed keywords

AB INITIO CALCULATIONS; ABSORPTION AREAS; AQUEOUS MEDIA; ASSOCIATION CONSTANT; B3LYP/6-31G; BASIC VIOLET 2; BINDING CONSTANT; FLUORESCENCE MAXIMA; FLUORESCENCE QUANTUM YIELD; GAUSSIANS; INCLUSION COMPLEX; NATURAL BOND ORBITAL ANALYSIS; TRIARYLMETHANES; UV-VIS ABSORPTIONS; VISIBLE SPECTROSCOPY;

ABSORPTION; ASSOCIATION REACTIONS; COMPLEXATION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PHOTOSENSITIZERS; QUANTUM YIELD;

ABSORPTION SPECTROSCOPY;

EID: 79961115434     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.06.027     Document Type: Article

References (50)

1. J. Morgan, and A.R. Oseroff Mitochondria-based photodynamic anti-cancer therapy Advanced Drug Delivery Reviews 49 2001 71 86 (Pubitemid 32493801)
2. T.S. Mang, M. Sullivan, M. Cooper, T. Loree, and N. Rigual The use of photodynamic therapy using 630 nm laser light and porfimer sodium for the treatment of oral squamous cell carcinoma Photodiagnosis and Photodynamic Therapy 3 2006 272 275 (Pubitemid 46053866)
3. T.J. Dougherty Photosensitizers: therapy and detection of malignant tumors Photochemistry and Photobiology 45 1987 879 889
4. B.W. Henderson, and T.J. Dougherty Photodynamic therapy: basic principles and clinical applications 1992 Marcel Dekker New York
5. J. Berlanda, T. Kiesslich, V. Engelhardt, B. Krammer, and K. Plaetzer Comparative in vitro study on the characteristics of different photosensitizers employed in PDT Journal of Photochemistry and Photobiology B: Biology 100 2010 173 180
6. S. Davis, M.J. Weiss, J.R. Wong, T.J. Lampidis, and L.B. Chen Mitochondrial and plasma membrane potentials cause unusual accumulation and retention of rhodamine 123 by human breast adenocarcinoma-derived MCF-7 cells The Journal of Biological Chemistry 260 1985 13844 13850 (Pubitemid 16233244)
7. G.L. Indig, S.H.D. Lacerda, B. Abraham, and T.C. Stringfellow Photophysical, photochemical, and tumor-selectivity properties of bromine derivatives of rhodamine-123 Photochemistry and Photobiology 81 2005 1430 1438 (Pubitemid 43035855)
8. I.K. Kandela, J.A. Bartlett, and G.L. Indig Effect of molecular structure on the selective phototoxicity of triarylmethane dyes towards tumor cells Photochemical & Photobiological Sciences 1 2002 309 314 (Pubitemid 37069741)
9. V. Fair, S. Thomas, S.C. Mathew, and K.G. Abhilash Recent advances in the chemistry of triaryl- and triheteroarylmethanes Tetrahedron 62 2006 6731 6747 (Pubitemid 43850561)
10. R.R. Allison, and C.H. Sibata Oncologic photodynamic therapy photosensitizers: a clinical review Photodiagnosis and Photodynamic Therapy 7 2010 61 75
11. J. Szejtli Introduction and general overview of cyclodextrin chemistry Chemical Reviews 98 1998 1743 1754
12. M. Wainwright Photodynamic antimicrobial chemotherapy (PACT) Journal of Antimicrobial Chemotherapy 42 1998 13 28 (Pubitemid 28356358)
13. R. Araújo Prates, A. Massayoshi Yamada Jr., L.C. Suzuki, M.C. Eiko Hashimoto, S. Cai, and S. Gouw-Soares Bactericidal effect of malachite green and red laser on Actinobacillus Actinomycetemcomitans Journal of Photochemistry and Photobiology B: Biology 86 2007 70 76 (Pubitemid 44841792)
14. S. Mauricio, M.S. Baptista, and G.L. Indig Effect of BSA binding on photophysical and photochemical properties of triarylmethane dyes Journal of Physical Chemistry B 102 1998 4678 4688 (Pubitemid 128578333)
15. +)-bovine serum albumin (BSA) system: evaluation of reaction paths and radical intermediates Journal of Photochemistry and Photobiology A: Chemistry 150 2002 59 66
16. J. Santhanalakshmi, and S. Balaji Binding studies of crystal violet on proteins Colloids and Surfaces A: Physicochemical and Engineering Aspects 186 2001 173 177 (Pubitemid 32505667)
17. J. Korppi-Tommola, and R.W. Yip Solvent effects on the visible absorption spectrum of crystal violet Canadian Journal of Chemistry 59 1981 191 194
18. L.M. Lewis, and G.L. Indig Solvent effects on the spectroscopic properties of triarylmethane dyes Dyes and Pigments 46 2000 145 154
19. A.D. Wolfe Influence of cationic triphenylmethane dyes upon DNA polymerization and product hydrolysis by Escherichia coli polymerase I Biochemistry 16 1 1977 30 33 (Pubitemid 8030060)
20. J. Preat, D. Jacquemin, V. Wathelet, J.M. André, and E.A. Perpte Towards the understanding of the chromatic behaviour of triphenylmethane derivatives Chemical Physics 335 2007 177 186
21. A.J. Kowaltowski, J. Turin, G.L. Indig, and A.E. Vercesi Mitochondrial effects of triarylmethane dyes Journal of Bioenergetics and Biomembranes 31 6 1999 581 590 (Pubitemid 30082901)
22. G.N. Lewis, Y.T. Magel, and D. Lipkin Isomers of crystal violet ion. Their absorption and re-emission of light Journal of the American Chemical Society 64 1942 1774 1782
23. V. Sundstöm, and T. Gillbro Effects of solvent on TMP photophysics. Transition from no barrier to barrier case, induced by solvent properties Journal of Chemical Physics 81 1984 3463 3475
24. F.T. Clark, and H.G. Drickamer The effect of pressure on the adsorption of crystal violet on oriented ZnO crystals Journal of Chemical Physics 81 1984 1024 1029
25. F.T. Clark, and H.G. Drickamer High-pressure study of triphenylmethane dyes in polymeric and aqueous media Journal of Physical Chemistry 90 4 1986 589 592
26. Y. Maruyama, M. Ishikawa, and H. Satozono Femtosecond isomerization of crystal violet in alcohols Journal of the American Chemical Society 118 1996 6257 6263 (Pubitemid 26236863)
27. A.H. Gomez de Mesquita, C.H. MacGillvry, and K. EriKs The structure of triphenylmethyl perchlorate at 85 °C Acta Crystallographica 18 3 1965 437 443
28. H.P.J.M. Dekkers, and E.C.M. Kielman-Van Luyt Magnetic circular dichroism of the triphenylcarbenium ion and some symmetrically para-substituted derivatives Molecular Physics 31 4 1976 1001 1019
29. L. Angeloni, G. Smulevich, and M.P. Marzocchi Resonance Raman spectrum of crystal violet Journal of Raman Spectroscopy 8 6 1979 305 310
30. J. Korppi-Tommola, and R.W. Yip Solvent effects on the visible absorption spectrum of crystal violet Canadian Journal of Chemistry 59 2 1981 191 194
31. H.B. Lueck, J.L. McHale, and W.D. Edwards Symmetry-breaking solvent effects on the electronic structure and spectra of a series of triphenylmethane dyes Journal of the American Chemical Society 114 7 1992 2342 2348
32. M.J. Bernard Bernard, J. García-Mora, D. Díaz, and G. Mendoza Díaz Molecular interactions and thermodynamic aspects of the complexation reaction between Gentian violet and several cyclodextrins Journal of Inclusion Phenomena and Macrocyclic Chemistry 34 1 1999 1 18
33. L. García-Río, A. Godoy, and J.R. Leis Spectroscopic characterisation of crystal violet inclusion complexes in β-cyclodextrin Chemical Physics Letters 401 2005 302 306
34. M.N. Montes de Oca, I. Aiassa, G. Argüello, and C. Ortiz Separation, purification, and characterization of analogues components of a commercial sample of New Fuchsin Journal of Chromatographic Science 48 2010 618 623
35. H. Benesi, and J. Hildebrand A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons Journal of the American Chemical Society 71 8 1949 2703 2707
36. M.V. Gaspar de Araujo, O.F.L. Macedo, C. Da Cunha Nascimento, L.S. Conegero, L.S. Barreto, and L.E. Almeida Characterization, phase solubility and molecular modeling of α-cyclodextrin/pyrimethamine inclusion complex Spectrochimica Acta Part A 72 2009 165 170
37. M.V. Gaspar de Araujo, E.K. Barbosa Vieira, G.S. Lázaro, L.S. Conegero, O.P. Ferreira, and L.E. Almeida Inclusion complexes of pyrimethamine in 2-hydroxypropyl-β-cyclodextrin: characterization, phase solubility and molecular modeling Bioorganic & Medicinal Chemistry 15 2007 5752 5759 (Pubitemid 47044973)
38. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Physical Review B 37 2 1988 785 789
39. A.D. Becke Density functional thermochemistry. III. The role of exact exchange Journal of Chemical Physics 98 7 1993 5648 5653
40. A.D. Becke A new mixing of Hartree-Fock and local density-functional theories Journal of Chemical Physics 98 2 1993 1372 1378
41. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03, Revision B.04 2003 Gaussian, Inc. Pittsburgh PA
42. T.K. Brunck, and F. Weinhold Quantum-mechanical studies on the origin of barriers to internal rotation about single bonds Journal of the American Chemical Society 101 7 1979 1700 1709
43. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO version 3.1.
44. C.E. Feliciano, and E. Quiñones The association of 4-(N, N-dimethylamino)benzonitrile and β-cyclodextrin in dimethyl sulfoxide and N, N-dimethylformamide Journal of Photochemistry and Photobiology A: Chemistry 120 1 1999 23 28
45. G. Zhang, S. Shuang, Z. Dong, C. Dong, and J. Pan Investigation on the inclusion behavior of neutral red with β-cyclodextrin, hydroxypropyl- β -cyclodextrin and sulfobutylether- β -cyclodextrin Analytica Chimica Acta 474 2002 189 195 (Pubitemid 35346454)
46. X. Zhu, J. Sun, and J. Wu Study on the inclusion interactions of β-cyclodextrin and its derivative with dyes by spectrofluorimetry and its analytical application Talanta 72 1 2007 237 242 (Pubitemid 46441344)
47. C.S. Oliveira, K.P. Branco, M.S. Baptista, and G.L. Indig Solvent and concentration effects on the visible spectra of tri-para-dialkylamino- substituted triarylmethane dyes in liquid solutions Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 58 13 2002 2971 2982 (Pubitemid 35384783)
48. L. García-Río, and A. Godoy Influence of CTACl cationic micelles on the spectral behavior of crystal violet Chemical Physics 327 2006 361 367
49. L. García-Río, P. Hervella, J.C. Mejuto, and M. Parajó Spectroscopic and kinetic investigation of the interaction between crystal violet and sodium dodecylsulfate Chemical Physics 335 2007 164 176
50. M. Tafazzoli, and M. Ghiasi Structure and conformation of α-, β- and γ-cyclodextrin in solution: theoretical approaches and experimental validation Carbohydrate Polymers 78 1 2009 10 15