Hydrazone molecules as mimics for acetylcholinesterase. A new route towards disposable biosensors for pesticides?

Autor(es)

Sgobbi, Livia F. ^[1] ; Pinho, Vagner D. ^[1] ; Cabral, Murilo F. ^[1] ; Burtoloso, Antonio C. B. ^[1] ; Machado, Sergio A. S. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: SENSORS AND ACTUATORS B-CHEMICAL; v. 182, p. 211-216, JUN 2013.
• Citações Web of Science: 4

Resumo

Acetylcholinesterase has been widely used in the development of biosensors for pesticide detection. However, there are few reports approaching the application in real samples, mainly due to the low stability, high cost and lack of enzymatic activity by pesticides adsorption. An alternative is the replacement by a low cost molecule that mimics the enzymatic behavior and allows the development of disposable devices, as those used for glucose evaluation in human blood. In this study, different hydrazone molecules were synthesized and tested as mimics for the acetylcholinesterase enzyme. Their actions in the hydrolysis of acetylthiocholine were demonstrated by UV-vis absorption measurements. The nucleophilic reaction was characterized by FUR and the reaction products (acetate and thiocholine) identified. The mimetic behavior was confirmed comparing the kinetic of the hydrolysis reaction of 4-{[}(1E)ethanehydrozanoyl]benzoic acid to that of other molecules as cyclopropyl methyl ketone hydrazone, 3-methyl-2-butanone hydrazone and hydrazine. The proposed molecules catalyzed acetylthiocholine hydrolysis being the 4-{[}(1E)ethanehydrozanoyl]benzoic acid faster than anyone else. Computational studies showed the substrate is attracted by the aromatic ring followed by the nucleophilic attack through the hydrazone group. This mimetic molecule can be used in order to develop a disposable biochemical sensor to be applied in the determination of acetylcholine or in the indirect determination of organophosphorous or carbamate pesticides. (C) 2013 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 12/08750-6 - Desenvolvimento de um biossensor mimético descartável para pesticidas organofosforados e carbamatos para o controle de qualidade de águas de abastecimento
• Beneficiário: Lívia Flório Sgobbi
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 08/09653-9 - Síntese total dos cardiotônicos pumiliotoxina 209 F e homopumiliotoxina 223 G
• Beneficiário: Vagner Dantas Pinho
• Modalidade de apoio: Bolsas no Brasil - Doutorado