Guest-host complex formed between ascorbic acid and β-cyclodextrin immobilized on the surface of an electrode

Molecules

Volumn 19, Issue 5, 2014, Pages 5952-5964

  Ramírez Silva, María Teresa ^a   Palomar Pardavé, Manuel ^b   Corona Avendaño, Silvia ^b   Romero Romo, Mario ^b   Alarcón Angeles, Georgina ^c  

^a DEPARTAMENTO DE QUÍMICA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA METROPOLITANA AZCAPOTZALCO   (Mexico)

^c DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

Author keywords

Ascorbic acid; Polymerization; Surface inclusion complex; cyclodextrin

Indexed keywords

ASCORBIC ACID; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CARBON;

CHEMISTRY; ELECTROCHEMISTRY; ELECTRODE; IMMOBILIZATION; OXIDATION REDUCTION REACTION; PH; SURFACE PROPERTY;

ASCORBIC ACID; BETA-CYCLODEXTRINS; CARBON; ELECTROCHEMISTRY; ELECTRODES; HYDROGEN-ION CONCENTRATION; IMMOBILIZATION; OXIDATION-REDUCTION; SURFACE PROPERTIES;

EID: 84901430512     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19055952     Document Type: Article

References (35)

1. Shaidarova, L.G.; Gedmina, A.V.; Chelnokova, I.A.; Budnikov, G.K. Electrocatalytic oxidation and flow-injection determination of ascorbic acid at a graphite electrode modified with a polyaniline film containing electrodeposited palladium. J. Anal. Chem. 2006, 61, 601-608.
2. Alarcón-Ángeles, G.; Corona-Avendaño, S.; Palomar-Pardavé, M.; Rojas-Hernández, A.; Romero-Romo, M.; Ramírez-Silva, M.T. Selective electrochemical determination of dopamine in the presence of ascorbic acid using sodium dodecyl sulfate micelles as masking agent. Electrochim. Acta 2008, 53, 3013-3020.
3. Corona-Avendaño, S.; Alarcón-Angeles, G.; Romero-Romo, M.; Cuán, A.; Ramírez-Silva, M.T.; Hernández-Martínez, L.; Palomar-Pardavé, M. Influence of CTAB on the electrochemical behavior of dopamine and on its analytic determination in the presence of ascorbic acid. J. Appl. Electrochem. 2010, 40, 463-474.
4. Corona-Avendaño, S.; Alarcón-Angeles, G.; Romero-Romo, M.; Merkoçi, A.; Rojas-Hernández, A.; Ramírez-Silva, M.T.; Palomar-Pardavé, M. Supramolecular systems construction for the selective quantitative determination of dopamine in the presence of ascorbic acid. Electrochem. Soc. Trans. 2011, 36, 385-392.
5. Alarcón-Ángeles, G.; Pérez-López, B.; Palomar-Pardavé, M.; Ramírez-Silva, M.T.; Alegret, S.; Merkoçi, A. Enhanced host-guest electrochemical recognition of dopamine using cyclodextrin in the presence of carbon nanotubes. Carbon 2008, 46, 898-906.
6. Colín-Orozco, E.; Ramírez-Silva, M.T.; Corona- Avendaño, S.; Romero-Romo, M.; Palomar-Pardavé, M. Electrochemical quantification of dopamine in the presence of ascorbic acid and uric acid using a simple carbon paste electrode modified with SDS micelles at pH 7. Electrochim. Acta 2012, 85, 307-313.
7. Fragoso, A.; Almirall, E.; Cao, R.; Echegoyen, L.; González-Jonte, R. A supramolecular approach to the selective detection of dopamine in the presence of ascorbate. Chem. Commun. 2004, 19, 2230-2231.
8. Wang, C.; Yuan, R.; Chai, Y.; Chen, S.; Zhang, Y.; Hu, F.; Zhang, M. Non-covalent iron(III)-porphyrin functionalized multi-walled carbon nanotubes for the simultaneous determination of ascorbic acid, dopamine, uric acid and nitrite. Electrochim. Acta 2012, 62, 109-115.
9. Zhang, L.; Shi, Z.; Lang, Q. Fabrication of poly(orthanilic acid)-multiwalled carbon nanotubes composite film-modified glassy carbon electrode and its use for the simultaneous determination of uric acid and dopamine in the presence of ascorbic acid. J. Solid State Electrochem. 2011, 15, 801-809.
10. Yang, S.; Li, G.; Yang, R.; Xia, M.; Qu, L. Simultaneous voltammetric detection of dopamine and uric acid in the presence of high concentration of ascorbic acid using multi-walled carbon nanotubes with methylene blue composite film-modified electrode. J. Solid State Electrochem. 2011, 15, 1909-1918.
11. Kalimuthu, P.; John, S.A. Electropolymerized film of functionalized thiadiazole on glassy carbon electrode for the simultaneous determination of ascorbic acid, dopamine and uric acid. Bioelectrochemistry 2009, 77, 13-18.
12. Ensafi, A.A.; Taei, M.; Khayamian, T.; Arabzadeh, A. Highly selective determination of ascorbic acid, dopamine, and uric acid by differential pulse voltammetry using poly(sulfonazo III) modified glassy carbon electrode. Sens. Actuators B 2010, 147, 213-221.
13. Ensafi, A.A.; Taei, M.; Khayamian, T. A differential pulse voltammetric method for simultaneous determination of ascorbic acid, dopamine, and uric acid using poly(3-(5-chloro-2-hydroxyphenylazo)-4,5-dihydroxynaphthalene-2,7- disulfonic acid) film modified glassy carbon electrode. J. Electroanal. Chem. 2009, 633, 212-220.
14. Lehn, J.M. Supramolecular chemistry. Science 1993, 260, 1762-1763.
15. Lehn, J.M. Supramolecular Chemistry; Wiley-VCH: New York, NY, USA, 1995; pp. 1-29.
16. Kaifer, A.E.; Gomez-Kaifer, M. Supramolecular Electrochemistry; Wiley-VCH: Weinheim, Germany; New York, NY, USA; Chichester, UK; Brisbane, Australia; Singapore, Singapore; Toronto, ON, Canada, 1999; pp. 89-125.
17. Wang, J.; Li, M.; Shi, Z.; Li, N.; Gu, Z. Electrocatalytic oxidation of norepinephrine at a glassy carbon electrode modified with single wall carbon nanotubes. Electroanalysis 2002, 14, 225-230.
18. Palomar-Pardav?, M.; Alarcsn-Angeles, G.; Ram?rez-Silva, M.T.; Romero-Romo, M.; Rojas-Hernandez, A.; Corona-Avenda?o, S. Electrochemical and spectrophotometric determination of the formation constants of the ascorbic acid-β-cyclodextrin and dopamine-β-cyclodextrin inclusion complexes. J. Incl. Phenom. Macrocycl. Chem. 2011, 69, 92-99.
19. Ikeda, H.; Nakamura, M.; Ise, N.; Oguma, N.; Nakamura, A.; Ikeda, T.; Toda, F.; Ueno, A. Fluorescent cyclodextrins for molecule sensing: Fluorescent properties, NMR characterization, and inclusion phenomena of n-dansylleucine-modified cyclodextrins. J. Am. Chem. Soc. 1996, 118, 10980-10998.
20. Roa-Morales, G.; Ramirez-Silva, T.; Galicia, L. Carbon paste electrodes electrochemically modified with cyclodextrins. J. Solid State Electrochem. 2003, 7, 355-360.
21. Corona-Avendaño, S.; Ramírez-Silva, M.T.; Romero-Romo, M.; Rojas-Hernández, A.; Palomar-Pardavé, M. Influence of the HClO4 concentration on the β-CD electropolimerization over a carbon paste electrode and on dopamine's electrochemical response. Electrochim. Acta 2013, 89, 854-860.
22. Ramírez, M.T.; Palomar, M.E.; González, I.; Rojas-Hernández, A. Carbon paste electrodes with electrolytic binder: Influence of the preparation method. Electroanalysis 1995, 7, 184-188.
23. Martínez, R.; Ramírez, M.T.; González, I. Voltammetric characterization of carbon paste electrodes with a nonconducting binder. Part I: Evidence of the influence of electroactive species dissolution into the paste on the voltammetric response. Electroanalysis 1998, 10, 336-342.
24. Xin, J.; Guo, Z.; Chen, X.; Jiang, W.; Li, J.; Li, M. Study of branched cationic β-cyclodextrin polymer/indomethacin complex and its release profile from alginate hydrogel. Int. J. Pharm. 2010, 386, 221-228.
25. Wu, W.; Liu, J.; Cao, S.; Tan, H.; Li, J.; Xu, F.; Zhang, X. Drug release behaviors of a pH sensitive semi-interpenetrating polymer network hydrogel composed of poly(vinyl alcohol) and star poly[2-(dimethylamino) ethylmethacrylate]. Int. J. Pharm. 2011, 416, 104-109.
26. He, Q.; Wu, W.; Xiu, K.; Zhang, Q.; Xu, F.; Li, J. Controlled drug release system based on cyclodextrin-conjugated poly(lactic acid)-β- poly(ethylene glycol) micelles. Int. J. Pharm. 2013, 443, 110-119.
27. Li, S.; Purdy, W.C. Cyclodextrins and their applications in analytical chemistry. Chem. Rev. 1992, 92, 1457-1470.
28. Gosser, D.K. Cyclic Voltametry Simulation and Analysis of Reaction Mechanisms; Wiley-VCH: Weinheim, Germany; New York, NY, USA; Chichester, UK; Brisbane, Australia; Singapore, Singapore; Toronto, ON, Canada, 1993; pp. 27-97.
29. Cobos-Murcia, J.A.; Galicia, L.; Rojas-Hernández, A.; Ramírez-Silva, M.T.; Álvarez-Bustamante, R.; Romero-Romo, M.; Rosquete-Pina, G.; Palomar-Pardave, M. Electrochemical polymerisation of 5-Amino-1,10-phenanthroline onto different substrates. Experimental and theoretical study. Polymer 2005, 46, 9053-9063.
30. Garfias-García, E.; Romero-Romo, M.; Ramírez-Silva, M.T.; Morales, J.; Palomar-Pardavé, M. Mechanism and kinetics of the electrochemical formation of polypyrrole under forced convection conditions. J. Electroanal. Chem. 2008, 613, 67-79.
31. De Licona-Sánchez, T.J.; Álvarez-Romero, G.A.; Mendoza-Huizar, L.H.; Galán-Vidal, C.A.; Palomar-Pardavé, M.; Romero-Romo, M.; Herrera-Hernández, H.; Uruchurtu, J.; Juárez-García, J.M. Nucleation and growth kinetics of electrodeposited sulfate-doped polypyrrole: Determination of the diffusion coefficient of SO4 2-in the polymeric membrane. J. Phys. Chem. B 2010, 114, 9737-9743.
32. Cuan, A.; Velasco, A.; Palomar-Pardav?, M.E.; Ram?rez-Silva, M.T.; Romero-Romo, M.; Cort?s-Romero, C.M.; Corona-Avenda?o, S. Quantumchemical calculations of the structural stability of β-cyclodextrin/dopamine and β-cyclodextrin/ascorbic acid systems. Electrochem. Soc. Trans. 2013, 47, 53-67.
33. Yi, S.Y.; Chan, H.Y.; Cho, H.H.; Park, Y.C.; Lee, S.H.; Bae, Z.U. Resolution of dopamine and ascorbic acid using nickel(II) complex polymer-modified electrodes. J. Electroanal. Chem. 2007, 602, 217-225.
34. Corona-Avendaño, S.; Alarcón-Ángeles, G.; Ramírez-Silva, M.T.; Rosquete-Pina, G.; Romero-Romo M.; Palomar-Pardavé, M. On the electrochemistry of dopamine in aqueous solution. Part I: The role of [SDS] on the voltammetric behavior of dopamine on a carbon paste electrode. J. Electroanal. Chem. 2007, 609, 17-26.
35. Palomar-Pardav, M.; Corona-Avendao, S.; Romero-Romo, M.; Alarcsn-ngeles, G.; Merkoi, A.; Ramrez-Silva, M.T. Supramolecular interaction of dopamine with β-cyclodextrin: An experimental and theoretical electrochemical study. J. Electroanal. Chem. 2014, 717-718, 103-109.