A Voltammetric Sensor Based on NiO Nanoparticle-Modified Carbon-Paste Electrode for Determination of Cysteamine in the Presence of High Concentration of Tryptophan
A carbon-paste electrode modified with ferrocenecarboxaldehyde and NiO nanoparticle (NiO/NPs) was used for the sensitive and selective voltammetric determination of cysteamine in the presence of tryptophan. The oxidation of cysteamine at the modified electrode was investigated by cyclic voltammetry (CV), chronoamperometry, and square-wave voltammetry (SWV). The values of the catalytic rate constant ( ) and diffusion coefficient ( ) for cysteamine were calculated. The modified electrode exhibits an efficient electron-mediating behavior together with well-separated oxidation peaks for cysteamine and tryptophan. At the optimum pH of 7.0 in a 0.1？M phosphate buffer solution, the SWV anodic peak currents showed a linear relationship versus cysteamine concentrations in the range of 0.09–300.0？μM and a detection limit of 0.06？μM. Finally, the proposed method was also examined as a selective, simple, and precise electrochemical sensor for the determination of cysteamine in real samples such as urine and capsule. 1. Introduction Cysteamine is a significant thiol drug for the treatment of cystinosis [1]. Since cysteamine therapy has become available for patients with nephropathic cystinosis (MIM219800) in the early 1980s, quality of life for these patients has greatly improved [2, 3]. The most frequent and most severe form, infantile cystinosis, is characterized by the development of renal Fanconi syndrome in the first year of life and leads to end-stage renal disease in the first decade of life when untreated [4]. Mutations in the CTNS gene, encoding for lysosomal cystine transporter cystinosin, are the causes of cystinosis [5]. Lysosomal accumulation of cystine, which is the hallmark of this autosomal recessive disorder, can be depleted by the aminothiol cysteamine [6]. Although treatment with cysteamine substantially decreases intracellular cystine accumulation, renal Fanconi syndrome is not cured, but end-stage renal disease can be postponed in the majority of the patients. Numerous chemical and instrumental techniques for detection of cysteamine have been reported [7–11]. Tryptophan (Trp), a vital constituent of proteins and a precursor for biologically important molecules such as the neurotransmitter serotonin and the neurohormone melatonin, is an amino acid essential to humans and animals due to its physiological roles [12]. It is also indispensable in human nutrition for establishing and maintaining a positive nitrogen balance [2]. In previous reports, spectroscopy [13], chemiluminescence [14], capillary electrophoresis [15], high-performance liquid
References
[1]
M. Keyvanfard, S. Sami, H. Karimi-Maleh, and K. Alizad, “Electrocatalytic determination of cysteamine using multiwall carbon nanotube paste electrode in the presence of 3, 4-dihydroxycinnamic acid as a homogeneous mediator,” Journal of the Brazilian Chemical Society, vol. 24, pp. 32–39, 2013.
[2]
M. Yudkoff, J. W. Foreman, and S. Segal, “Effects of cysteamine therapy in nephropathic cystinosis,” The New England Journal of Medicine, vol. 304, no. 3, pp. 141–145, 1981.
[3]
W. A. Gahl, “Early oral cysteamine therapy for nephropathic cystinosis,” European Journal of Pediatrics, Supplement, vol. 162, no. 1, pp. S38–S41, 2003.
[4]
W. A. Gahl, J. G. Thoene, and J. A. Schneider, “Cystinosis: a disorder of lysosomal membrane transport,” in The Metabolic and Molecular Bases of Inherited Disease, C. R. Scriver, A. L. Beaudet, W. S. Sly, and D. Valle, Eds., pp. 5085–6108, McGraww-Hill, New York, NY, USA, 2001.
[5]
M. Town, G. Jean, S. Cherqui et al., “A novel gene encoding an integral membrane protein is mutated in nephropathic cystinosis,” Nature Genetics, vol. 18, no. 4, pp. 319–324, 1998.
[6]
W. A. Gahl, F. Tietze, J. Butler DeB., and J. D. Schulman, “Cysteamine depletes cystinotic leucocyte granular fractions of cystine by the mechanism of disulphide interchange,” Biochemical Journal, vol. 228, no. 3, pp. 545–550, 1985.
[7]
M. Stachowicz, B. Lehmann, A. Tibi, P. Prognon, V. Daurat, and D. Pradeau, “Determination of total cysteamine in human serum by a high-performance liquid chromatography with fluorescence detection,” Journal of Pharmaceutical and Biomedical Analysis, vol. 17, no. 4-5, pp. 767–773, 1998.
[8]
H. Kataoka, Y. Imamura, H. Tanaka, and M. Makita, “Determination of cysteamine and cystamine by gas chromatography with flame photometric detection,” Journal of Pharmaceutical and Biomedical Analysis, vol. 11, no. 10, pp. 963–969, 1993.
[9]
A. J. Jonas and J. A. Schneider, “Measurement of total plasma cysteamine using high-performance liquid chromatography with electrochemical detection,” Analytical Biochemistry, vol. 114, pp. 429–432, 1981.
[10]
M. Keyvanfard, A. A. Ensafi, and H. Karimi-Maleh, “A new strategy for simultaneous determination of cysteamine in the presence of high concentration of tryptophan using vinylferrocene-modified multiwall carbon nanotubes paste electrode,” Journal of Solid State Electrochemistry, vol. 16, no. 9, pp. 2949–2955, 2012.
[11]
A. Taherkhani, H. Karimi-Maleh, A. A. Ensafi et al., “Simultaneous determination of cysteamine and folic acid in pharmaceutical and biological samples using modified multiwall carbon nanotube paste electrode,” Chinese Chemical Letters, vol. 23, no. 2, pp. 237–240, 2012.
[12]
C. Li, Y. Ya, and G. Zhan, “Electrochemical investigation of tryptophan at gold nanoparticles modified electrode in the presence of sodium dodecylbenzene sulfonate,” Colloids and Surfaces B: Biointerfaces, vol. 76, no. 1, pp. 340–345, 2010.
[13]
D. M. Reynolds, “Rapid and direct determination of tryptophan in water using synchronous fluorescence spectroscopy,” Water Research, vol. 37, no. 13, pp. 3055–3060, 2003.
[14]
Z. Lin, X. Chen, Z. Cai, P. Li, X. Chen, and X. Wang, “Chemiluminescence of tryptophan and histidine in Ru(bpy)32+-KMnO4aqueous solution,” Talanta, vol. 75, no. 2, pp. 544–550, 2008.
[15]
I. Ilisz, G. Fodor, R. Berkecz, R. Iványi, L. Szente, and A. Pétera, “Enantioseparation of β-substituted tryptophan analogues with modified cyclodextrins by capillary zone electrophoresis,” Journal of Chromatography A, vol. 1216, no. 15, pp. 3360–3365, 2009.
[16]
C. Bayle, N. Siri, V. Poinsot, M. Treilhou, E. Causse, and F. Couderc, “Analysis of tryptophan and tyrosine in cerebrospinal fluid by capillary electrophoresis and “ball lens” UV-pulsed laser-induced fluorescence detection,” Journal of Chromatography A, vol. 1013, no. 1-2, pp. 123–130, 2003.
[17]
M. Keyvanfard, R. Shakeri, H. Karimi-Maleh, and K. Alizad, “Highly selective and sensitive voltammetric sensor based on modified multiwall carbon nanotube paste electrode for simultaneous determination of ascorbic acid, acetaminophen and tryptophan,” Materials Science and Engineering C, vol. 33, no. 2, pp. 811–816, 2013.
[18]
M. Fouladgar, H. Karimi-Maleh, and R. Hosseinzadeh, “Novel nanostructured electrochemical sensor for voltammetric determination of N-acetylcysteine in the presence of high concentrations of tryptophan,” Ionics, vol. 19, pp. 665–672, 2013.
[19]
X. Tang, Y. Liu, H. Hou, and T. You, “Electrochemical determination of L-Tryptophan, L-Tyrosine and L-Cysteine using electrospun carbon nanofibers modified electrode,” Talanta, vol. 80, no. 5, pp. 2182–2186, 2010.
[20]
A. A. Ensafi and H. Karimi-Maleh, “Modified multiwall carbon nanotubes paste electrode as a sensor for simultaneous determination of 6-thioguanine and folic acid using ferrocenedicarboxylic acid as a mediator,” Journal of Electroanalytical Chemistry, vol. 640, no. 1-2, pp. 75–83, 2010.
[21]
A. A. Ensafi, H. Karimi-Maleh, S. Mallakpour, and B. Rezaei, “Highly sensitive voltammetric sensor based on catechol-derivative-multiwall carbon nanotubes for the catalytic determination of captopril in patient human urine samples,” Colloids and Surfaces B, vol. 87, no. 2, pp. 480–488, 2011.
[22]
A. A. Ensafi, H. Karimi-Maleh, S. Mallakpour, and M. Hatami, “Simultaneous determination of N-acetylcysteine and acetaminophen by voltammetric method using N-(3,4-dihydroxyphenethyl)-3,5-dinitrobenzamide modified multiwall carbon nanotubes paste electrode,” Sensors and Actuators, B, vol. 155, no. 2, pp. 464–472, 2011.
[23]
H. Karimi-Maleh, P. Biparva, and M. Hatami, “A novel modified carbon paste electrode based on NiO/CNTs nanocomposite and (9, 10-dihydro-9, 10-ethanoanthracene-11, 12-dicarboximido)-4-ethylbenzene-1, 2-diol as a mediator for simultaneous determination of cysteamine, nicotin amide adenine dinucleotide and folic acid,” Biosensors and Bioelectronics, vol. 48, pp. 270–275, 2013.
[24]
T. Tavana, M. A. Khalilzadeh, H. Karimi-Maleh, A. A. Ensafi, H. Beitollahi, and D. Zareyee, “Sensitive voltammetric determination of epinephrine in the presence of acetaminophen at a novel ionic liquid modified carbon nanotubes paste electrode,” Journal of Molecular Liquids, vol. 168, pp. 69–74, 2012.
[25]
S. Salmanpour, T. Tavana, A. Pahlavan et al., “Voltammetric determination of norepinephrine in the presence of acetaminophen using a novel ionic liquid/multiwall carbon nanotubes paste electrode,” Materials Science and Engineering C, vol. 32, pp. 1912–1918, 2012.
[26]
H. Beitollah, M. Goodarzian, Khalilzadeh et al., “Electrochemical behaviors and determination of carbidopa on carbon nanotubes ionic liquid paste electrode,” Journal of Molecular Liquids, vol. 173, pp. 137–143, 2012.
[27]
J.-B. Raoof, R. Ojani, and H. Karimi-Maleh, “Carbon paste electrode incorporating 1-[4-(ferrocenyl ethynyl) phenyl]-1-ethanone for electrocatalytic and voltammetric determination of tryptophan,” Electroanalysis, vol. 20, no. 11, pp. 1259–1262, 2008.
[28]
M. Elysi and M. A. Khalilzadeh, “High sensitive voltammetric sensor based on pt/CNTs nanocomposite modified ionic liquid carbon paste electrode for deter, mination of Sudan I in food samples,” Food Chemistry, vol. 141, pp. 4311–4317, 2013.
[29]
E. Afsharmanesh, H. Karimi-Maleh, A. Pahlavan, and J. Vahedi, “Electrochemical behavior of morphine at ZnO/CNT nanocomposite room temperature ionic liquid modified carbon paste electrode and its determination in real samples,” Journal of Molecular Liquids, vol. 181, pp. 8–13, 2013.
[30]
H.J. Jeon, S.C. Yi, and S.G. Oh, “Preparation and antibacterial effects of Ag–SiO2thin films by sol-gel method,” Biomaterials, vol. 24, no. 27, pp. 4921–4928, 2003.
[31]
A. A. Ensafi, E. Khoddami, B. Rezaei, and H. Karimi-Maleh, “P-Amiophenol -multiwall carbon nanotube-Tio2 electrode as a sensor for simulations determination of pencillamine and uric acid,” Colloid and Surface B, vol. 81, pp. 42–29, 2010.
[32]
H. Beitollahi, H. Karimi-Maleh, and H. Khabazzadeh, “Nanomolar and selective determination of epinephrine in the presence of norepinephrine using carbon paste electrode modified with carbon nanotubes and novel 2-(4-oxo-3-phenyl-3,4-dihydroquinazolinyl)-N′-phenyl- hydrazinecarbothioamide,” Analytical Chemistry, vol. 80, no. 24, pp. 9848–9851, 2008.
[33]
M. Roodbari Shahmiri, A. Bahari, H. Karimi-Maleh, R. Hosseinzadeh, and N. Mirnia, “Ethynylferrocene-NiO/MWCNT /MWCNT nanocomposite modified carbon paste electrode as a novel voltammetric sensor for simultaneous determination of glutathione and acetaminophen,” Sensors and Actuators B: Chemical, vol. 177, pp. 70–77, 2013.
[34]
R. Moradi, S. A. Sebt, H. Karimi-Maleh et al., “Synthesis and application of FePt/CNTs nanocomposite as a sensor and novel amide ligand as a mediator for simultaneous determination of glutathione, nicotinamide adenine dinucleotide and tryptophan”,” Physical Chemistry Chemical Physics, vol. 15, no. 16, pp. 5888–5897, 2013.
[35]
M. Bijad, H. Karimi-Maleh, and M. A. Khalilzadeh, “Application of ZnO/CNTs nanocomposite ionic liquid paste electrode as a sensitive voltammetric sensor for determination of ascorbic acid in food samples,” Food Analytical Methods, 2013.
[36]
M. Fouladgar, H. Karimi-Maleh, and R. Hosseinzadeh, “Novel nanostructured electrochemical sensor for voltammetric determination of N-acetylcysteine in the presence of high concentrations of tryptophan,” Ionics, vol. 19, no. 4, pp. 665–672, 2013.
[37]
H. Karimi-Maleh, A. A. Ensafi, and H. R. Ensafi, “Ferrocenedicarboxylic acid modified carbon paste electrode: a sensor for electrocatalytic determination of hydrochlorothiazide,” Journal of the Brazilian Chemical Society, vol. 20, no. 5, pp. 880–887, 2009.
[38]
Z. Galus, Fundumentals of Electrochemical Analysis, Ellis Horwood, New York, NY, USA, 1976.
[39]
A. A. Ensafi and H. Karimi-Maleh, “A voltammetric sensor based on modified multiwall carbon nanotubes for cysteamine determination in the presence of tryptophan using p-aminophenol as a mediator,” Electroanalysis, vol. 22, no. 21, pp. 2558–2568, 2010.
