Um método para determinação voltamétrica simultânea de triptamina e histamina usando eletrodo de carbono vítreo modificado com pontos quânticos de carbono

Authors

  • Tassio de Araújo Nunes
  • Anabel Santos Lourenço
  • Amanda Cecília da Silva
  • Mário César Ugulino de Araújo

DOI:

https://doi.org/10.34117/bjdv9n8-160

Keywords:

método voltamétrico, eletrodo de carbono vítreo modificado, pontos quânticos de carbono, triptamina, histamina

Abstract

A triptamina e a histamina são aminas biogênicas formadas pela degradação de compostos nitrogenados de matéria orgânica que apresentam potencial risco de desenvolvimento de atividades toxicológicas em seres humanos. Por isso, é fundamental o controle e o monitoramento desses compostos em alimentos e bebidas. A literatura reporta a utilização dos métodos cromatográficos para a determinação dessas aminas biogênicas em baixos níveis de concentração em diversas matrizes. Porém, esses métodos cromatográficos são lentos e apresentam alto consumo de solventes e reagentes prejudiciais à saúde e ao meio ambiente e um alto custo de operação, manutenção e aquisição dos equipamentos e insumos laboratoriais. Para superar esses inconvenientes, uma boa alternativa é o desenvolvimento de métodos voltamétricos para determinação de triptamina e histamina em alimentos em baixos níveis de concentração. Com base nisso, neste trabalho foi desenvolvido com sucesso um novo sensor (o ECV-PQCs/β-CD) e um método voltamétrico rápido, simples, sensível e barato para determinação simultânea de triptamina e histamina. O sensor ECV-PQCs/β-CD utiliza um eletrodo de carbono vítreo (ECV) modificado com pontos quânticos de carbono (PQCs), obtidos a partir do ácido cítrico, e β-ciclodextrina (β-CD). A modificação do ECV consistiu na realização de 8 varreduras de 50 mV s-1 consecutivas em tampão acetato pH 4,5, utilizando voltametria cíclica e uma mistura de pontos quânticos de carbono e β-ciclodextrina. O método voltamétrico proposto apresentou uma faixa linear de resposta e limite de detecção de 12,5 a 25,0 μmol L-1 e 0,25 μmol L-1 para triptamina e 25,0 a 50,0 μmol L-1 e 0,68 μmol L-1 para histamina.

References

ALGARRA, M.; GONZÁLEZ-CALABUIG, A.; RADOTIC, C.; MUTAVDZIC, D.; ANIA, C.O.; LAZARO-MARTINEZ, J.M.; JIMENEZ-JIMENEZ, J.; RODRIGUEZ-CASTELLON, E.; VALLE, M. Enhanced electrochemical response of carbon quantum dot modified electrodes. Talanta, v.178, p.679, 2018.

ANLI, R. E., VURAL, N., YILMAZ, S., & VURAL, Y. H. The determination of biogenicamines in Turkish red wines. Journal of Food Composition and Analysis, n.17, p. 53–62, 2004.

BAKER, S. N.; BAKER, G. A. Luminescent carbon nanodots: emergent nanolights. Angewandte Chemie International Edition, v.49, p.6726, 2010.

BARD, A. J.; FAULKNER, L. R., Electrochemical Methods Fundamentals and Applications. 2ª ed. New York: John Wiley & Sons, INC, 2001.

BHADRA, B. N.; SONG, J. Y.; LEE, S. -K.; HWANG, Y. K.; JHUNG, S. H. Adsorptive removal of aromatic hydrocarbons from water over metal azolate framework-6-derived carbons. Journal of Hazardous Materials, v.344, p.1069- 1077, 2018.

BIGGER, C.A.; PONTEN, I.; PAGE, J.E.; DIPPLE, A. Mutational spectra for polycyclic aromatic hydrocarbons in the supF target gene. Mutation Research, v.450, p.75, 2000.

BUENO-SOLANO, C.; LÓPEZ-CERVANTES, J.; SÁNCHEZ-MACHADO, D. I.; CAMPAS-BAYPOLI, O. N. HPCL determination of histamine, tyramine and amino acids in shrimp by-products. Journal of the Brazilian Chemical Society, v. 1, n. 23, p. 96–102, 2012.

Brett, A. M. O.; Brett, C. M. A. Eletroquímica princípios, métodos e aplicações. Coimbra: Livraria Almedina, 1996.

CAO, L.; WANG, X.; MEZIANI, M. J.; LU, F.; WANG, H.; LUO, P. G.; LIN, Y.; HARRUFF, B. A.; VECA, L. M.; MURRAY, D.; XIE, S.-Y.; SUN, Y.-P. Carbon dots for multiphoton bioimaging. Journal of The American Chemical Society, v.129, p.11318, 2007.

CHEN, J.; HE, P.; BAI, H.; HE, S.; ZHANG, T.; ZHANG, X.; DONG, F. Poly(βcyclodextrin)/carbon quantum dots modified glassy carbon electrode: Preparation, characterization and simultaneous electrochemical determination of dopamine, uric acid and tryptophan. Sensors and Actuators B: Chemical, v.252, p.9–16, 2017.

COSTA, D. J. E.; MARTÍNEZ, A. M.; RIBEIRO, W. F.; BICHINHO, K.M.; DI NEZIO, M.S.; PISTONESI, M.F.; ARAUJO, M.C.U. Determination of tryptamine in foods using square wave adsorptive stripping voltammetry. Talanta. v.154, p.134–140, 2016.

CONTRERAS, M. et al. Determinación de aminas biógenas en quesos madurados. Rev. Cient., Maracaibo, v.17, n.1, p.89-95, 2007.

FERNÁNDEZ-GARCÍA, E. J. T.; NUNEZ, M. Formation of biogenic amines in raw milk Hispánico cheese manufactured with proteinases and different levels of starter culture. J Food Prot. v.63, v.11, p.1551-1555, 2000.

FDA (CFSAN). Scombrotoxin (histamine) formation. In: Department of Health and Human Services, Public Health Service, Food and Drug Administration, Center for Food Safety and Applied Nutrition, Office of Seafood. Fish and fishery products hazards and controls guide. 3rd ed. Washington: Department of Health and Human Services, Public Health Service, Food and Drug Administration, Center for Food Safety and Applied Nutrition, Office of Seafood, 2001.

FU, L.; WANG, A.; LAI, G.; LIN C.T.; YU, J.; YU, A.; LIU, ZHONG, XIE, K.; SU, W. Correction to: A glassy carbon electrode modified with N-doped carbon dots for improved detection of hydrogen peroxide and paracetamol. Microchimica Acta, 2019.

GARAI, G.; DUENAS, M.T.; IRASTORZA, A.; MORENO-ARRIBAS, M.V. Biogenic amine production by lactic acid bacteria isolated from cider. Lett Appl Microbiol, v.5, n.45, p. 473-478, 2007.

GOMES, M. B.; PIRES, B. A. D.; FRACALANZZA, S. A. P., & MARIN, V. A. O risco das aminas biogênicas nos alimentos. Ciência & Saúde Coletiva, v.4, n.19, p. 1123–1134, 2014.

HERNÁNDEZ-JOVER, T.; IZQUIERDO-PULIDO, M.; VECIANA-NOGUES, M. T.; MARINE-FONT A.; VIDAL-CAROU, M. C. Biogenic amine and polyamine contents in meat and meat products. Journal of Agriculture Food Chemical, v. 6, n.45, p. 2098-2102, 1997.

HOLLER, F. J.; SKOOG, D. A.; CROUCH, S. R. Principles of instrumental analysis. 6 ed. Bookman, 2009.

HU, S.L.; NIU, K.Y.; SUN, J.; YANG, J.; ZHAO, N.Q.; DU, X.W. One-step synthesis of fluorescent carbon nanoparticles by laser irradiation. Journal of Materials Chemistry, v.19, p.484, 2009.

IARC – International Agency for Research on Cancer. Monographs on the Evaluation of Carcinogenic Risks to Humans, v.92, p.773, 2010.

IARC, International Agency for Research on Cancer. Monographs on the evaluation of carcinogenic risk of chemicals to humans. 2006. [Acesso em 10/04/2023]. Disponível em: http://monographs.iarc.fr/wp-content/uploads/2018/06/mono98.pdf.

IUPAC. International Union of Pure and Applied Chemistry. Nomenclature, symbol, units and their usage in spectrochemical analysis. II. Data interpretation. Spectrochimica Acta Part B: Atomic Spectroscopy, 33, 241 – 246, 1978. DOI: 10.1016/0584-8547(78)80044-5.

JASTRZEBSKA, A.; PIASTA, A.; KOWALSKA, S.; KRZEMIŃSKI, M.; SZŁYK, E. A new derivatization reagent for determination of biogenic amines in wines. J Food Comp and Analysis. v.48, p.111–119, 2016.

JIONG, L.; PEI SHAN EMMELINE, Y.; CHEE KWAN, G.; PING, W.; KIAN PING, L. Transforming C60 molecules into graphene quantum dots. Nature Nanotechnology, v.6, p247. 2011.

KALAC, P., HLAVATA, V., & KRIZEK, M. Concentrations of five biogenic amines in Czech beers and factors affecting their formation. Food Chemistry, n.58, p. 209–214, 1997.

KALAC, P. Recent advances in the research on biological roles of dietary polyamines in man. Journal of Applied Biomedicine, v. 2, n.7, p. 65-74, 2009.

KIM, M.K; MAH J.H; HWANG, H.J. Biogenic amine formation and bacterial contribution in fish, squid and shellfish. Food Chemical, v. 1, n.116, p. 87-95, 2009.

KWON, W.; KIM, Y.-H.; LEE, C.-L.; LEE, M.; CHOI, H. C.; LEE, T.-W.; RHEE, S.-W. Electroluminescence from graphene quantum dots prepared by amidative cutting of tattered graphite. Nano Letters, v.14, p. 1306, 2014.

LANDETE, J.M.; DE LAS RIVAS, B.; MARCOBAL, A.; MUÑOZ, R. Molecular methods for the detection of biogenic amine-producing bacteria on foods. Int J Food Microbiol, v.117, n.3, p.258-269, 2007.

LI, H.; HE, X.; KANG, Z.; HUANG, H.; LIU, Y.; LIU, J.; LIAN, S.; TSANG, C. H. A.; YANG, X.; LEE, S.T. Water-soluble fluorescent carbono quantum dots and photocatalyst design. Angewandte Chemie International Edition, v.49, p.4430, 2010.

LI, H.; KANG, Z.; LIU, Y.; LEE, S.-T. Carbon nanodots: synthesis, properties and applications. Journal of Materials Chemistry, v.22, p.24230, 2012.

LI, Q.; XU, Z.; TANG, W.; WU, Y. Determination of Dopamine with a Modified Carbon Dot. ElectrodeAnalytical Letters, v.2040. 2015.

LIU, R.; WU, D.; LIU, S.; KOYNOV, K.; KNOLL, W.; LI, Q. An aqueous route to multicolor photoluminescent carbon dots using sílica spheres as carriers. Angewandte Chemie International Edition, v.48, p.4598, 2009.

LOUKOU, Z., & ZOTOU, A. Determination of biogenic amines as dansyl derivatives in alcoholic beverages by high-performance liquid chromatography with fluorimetric detection and characterization of the dansylated amines by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry. Journal of Chromatography A, n.996, p.103–113, 2003.

LOURENÇO, A. S.; NUNES, T. A.; SILVA, A. C.; RIBEIRO, W. F.; ARAUJO, M. C. U. Simultaneous Voltammetric Determination of Tryptamine and Histamine in Wines Using a Carbon Paste Electrode Modifed with Nickel Phthalocyanine. Food Analytical Methods. v.15, p.3257–3269, 2022.

LU, J.; YANG, J.-X.; WANG, J.; LIM, A.; WANG, S.; LOH, K. P. One-pot synthesis of fluorescente carbon nanoribbons, nanoparticles, and graphene by the exfoliation of graphite in ionic liquids. ACS Nano, v.3, p.2367, 2009.

MACHADO, C.E.; VIEIRA, K.O.; FERRARI, J.L.; SCHIAVON, M.A. Pontos quânticos de carbono: síntese química, propriedades e aplicações. Rev. Virtual Quim. v.7, p.1306-1346, 2015.

MARCOBAL, A.; de LAS RIVAS, B.; MORENO-ARRIBAS MV, MUNÕZ, R. Identification of the ornithine decarboxylase gene in the putrescine-producer Oenococcus oeni BIFI-83. FEMS Microbiol Lett, v. 2, n.239, p.213-220, 2004.

MAIJALA, R.L. Formation of histamine and tyramine by some lactic acid bacteria in MRS broth and modified decarboxylation agar. Lett Appl Microbiol, v. 1, n.17, p. 40-43, 1993.

MIRTCHEV, P.; HENDERSON, E. J.; SOHEILNIA, N.; YIP, C. M.; OZIN, G. A.Solution phase synthesis of carbon quantum dots as sensitizers for nanocrystalline TiO2 solar cells. Journal of Materials Chemistry, v.22, p.1265, 2012.

MORENO-ARRIBAS, V.; POLO, M.C.; JORGANES, F.; MUNOZ, R. Screening of biogenic amine production by lactic acid bacteria isolated from grape must and wine. Int J Food Microbiol, v. 2, n.84, p.117-123, 2003.

MOHAN, C.O.; RAVISHANKAR, C.N.; GOPAL, T.K.S.; KUMAR, K.A.; LALITHA, K.V. Biogenic amines formation in seer fish (Scomberomorus commerson) steaks packed with O2 scavenger during chilled storage. Food Research International, v. 3, n.42, p. 411-416, 2009.

NAILA, A.; FLINT, S.; FLETCHER, G.; BREMER, P.; MEERDINK, G. Control of Biogenic Amines in Food—Existing and Emerging Approaches. J Food Sci, v. 7, n.75, p. 139- 150, 2010.

PACHECO, W. F.; SEMAAN, F. S.; ALMEIDA, V. G. K.; RITTA, A. G. S. L.; AUCÉLIO, R. Q. Voltametrias: Uma Breve Revisão Sobre os Conceitos. Rev. Virtual Quim., v.5, n.4, p.516-537, 2013

PAN, D.; GUO, L.; ZHANG, J.; XI, C.; XUE, Q.; HUANG, H.; LI, J.; ZHANG, Z.; YU, W.; CHEN, Z.; LI, Z.; WU, M. Cutting sp2 clusters in graphene sheets into colloidal graphene quantum dots with Strong green fluorescence. Journal of Materials Chemistry, 22, 3314, 2012.

PENG, H.; TRAVAS-SEJDIC, J. Simple aqueous solution route to luminescent carbogenic dots from carbohydrates. Chemistry of Materials, 21, 5563. 2009.

PLAMBECK, J. A.; Electroanalytical Chemistry: Basic Principles and Applications, John Wiley & Sons: New York, 1982.

RIO, B.; REDRUELLO, B.; FERNANDEZA, M.; MARTINA, M. C.; LADERO, V.; ALVAREZ, M. A. The biogenic amine tryptamine, unlike β-phenylethylamine, shows in vitro cytotoxicity at concentrations that have been found in foods. Food Chem. v.331, p.127303, 2020.

ROMANO, A.; KLEBANOWSKI, H.; LA GUERCHE, S.; BENEDUCE, L.; SPANO, G.; MURAT, M. L.; LUCAS, P. Determination of biogenic amines in wine by thin-layer chromatography/densitometry. Food Chem. v.135, p.1392–1396, 2012.

SHEN, M.; LIU, G.; YIN, H.; ZHOU, L. Distribution, sources and health risk of PAHs in urban air-conditioning dust from Hefei, East China. Ecotoxicology and Environmental Safety. v.194, p.110442, 2020.

SKOOG, D. A.; HOLLER, F. J.; NIEMAN T. A. Princípios de análise Instrumental. 5ª Ed. Porto Alegre: Bookman, 2002.

SKOOG, D. A.; WEST, D. M.; HOLLER, F. J.; CROUCH, S. R. Fundamentals of analytical chemistry. Mason: Cengage Learning, 2013.

SMITH, E. T. Examination of n=2 reaction mechanisms that reproduce pH-dependent reduction potentials. Analytica Chimica Acta, v.572, n.259, 2006.

SOARES, F. S; RAMALHO, R. T. E; SILVA, A. C. A voltammetric method for diuron determination in river water. Electroanalysis, v.35, 2023.

SOUZA, D. DE; MACHADO, S. A. S.; AVACA, L. A.; Voltametria de onda quadrada. Primeira parte: aspectos teóricos. Química Nova, v.26, p.81-89, 2003.

SOUZA, S.C.; THEODORO, K.H.; SOUZA, É.R.; DA MOTTA, S.; GLÓRIA, M.B.A. Bioactive amines in Brazilian wines: types, levels and correlation with physico-chemical parameters Brazilian. Arch. Biol Technol. v.48, p.53–62, 2005.

STOJANOVIĆ, Z. S.; MEHMETI, E.; KALCHER, K.; GUZSVÁNY, V.; STANKOVIĆ, D.M. SWCNT-modifed carbon paste electrode as an electrochemical sensor for histamine determination in alcoholic beverages. Food Anal Methods, v. 9, p.2701–2710, 2016.

SUN, X.; LEI, Y. Fluorescent carbon dots and their sensing applications. Trends Analyt. Chem., v.89, p.163, 2017.

TANG, H.; DARWISH, W. S., EL-GHAREEB, W. R. Microbial quality and formation of biogenic amines in the meat and edible offal of Camelus dromedaries with a protection trial using gingerol and nisin. Food Sci Nutr. v.8: p.2094– 2101, 2020

TIAN, L.; GHOSH, D.; CHEN, W.; PRADHAN, S.; CHANG, X.; CHEN, S. Nanosized carbono particles from natural gas soot. Chemistry of Materials, v.21, p.2803, 2009.

TIL, H.P.; FALKE, H.E.; PRINSEN, M.K.; WILLEMS, M.I. Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats. Food Chem Toxicol; v.35, p.337-348, 1997.

TVRDIKOVA, J.; DANHEL, A.; VYSKOCIL, V.; BAREK, J. Voltammetric Determination of Dinitronaphthalenes Using a Silver Solid Amalgam Paste Electrode. Analytical Sciences, v. 28, p. 411, 2012.

USLU, B.; OZKAN, S. A. Solid Electrodes in electroanalytical chemistry: present applications and prospects for high throughput screening of drug compounds. Combinatorial Chemistry and High Throughput Screening, v.10, p. 495, 2007.

WANG, F.; KREITER, M.; HE, B.; PANG, S.; LIU, C. Y. Synthesis of direct whitelight emitting carbogenic quantum dots. Chemical Communications, p.3309, 2010.

WANG, J.; Analytical Electrochemistry, 2 aed., Wiley-VCH: New Jersey, 2000.

WANG, J.; QIU, J. A review of carbon dots in biological applications. J. Mater. Sci., v.51, p.4728, 2016.

WANG, X.; QU, K.; XU, B.; REN, J.; QU, X. Microwave assisted one-step green synthesis of cell-permeable multicolor photoluminescent carbon dots without surface passivation reagents. Journal of Materials Chemistry, v.21, p.2445, 2011.

WANG, Y.; HU, A. Carbon quantum dots: synthesis, properties and applications. J. Mater. Chem. C. v.2, p.6921-6940, 2014.

XU, X.; RAY, R.; GU, Y.; PLOEHN, H.J.; GEARHEART, L.; RAKER, K.; SCRIVENS, W.A. Electrophoretic analysis and purification of fluorescent single-walled carbon nanotube fragments. J. Am. Chem. Soc. v.126, p.12736-12737, 2004.

YANG, S.T.; CAO, L.; LUO, P. G.; LU, F.; WANG, X.; WANG, H.; MEZIANI, M. J.; LIU, Y.; QI, G.; SUN, Y.P. Carbon dots for optical imaging in vivo. Journal of the American Chemical Society, v.131, p.11308, 2009.

YU, S.J.; KANG, M.W.; CHANG, H.C.; CHEN, K.M.; YU, Y.C. Bright fluorescente nanodiamonds: no photobleaching and low cytotoxicity. Journal of the American Chemical Society, v.127, p.17604. 2005.

Published

2023-08-31

How to Cite

Nunes, T. de A., Lourenço, A. S., da Silva, A. C., & de Araújo, M. C. U. (2023). Um método para determinação voltamétrica simultânea de triptamina e histamina usando eletrodo de carbono vítreo modificado com pontos quânticos de carbono. Brazilian Journal of Development, 9(8), 25546–25566. https://doi.org/10.34117/bjdv9n8-160

Issue

Section

Original Papers