Preparation of ferrocene core dendrimers and immobilization of AChE for detection of diclofop-methyl herbicide

Nurdan Kurnaz Yetim, Nurşen Sari

Abstract


The aim of this work was to investigate diclofop-methyl detection (found in a variety of herbicides) using novel dendrimers that have ferrocene cores, as well as their Pt(II) and Pt(IV) complexes. Novel dendrimer structures were synthesized and characterized by molar conductivity, magnetic susceptibility, FTIR, UV-Vis, 1H-NMR and LC-MS methods. Then, the AChE (acetylcholine esterase) enzyme was immobilized on the novel dendrimers, and the optimal parameters (pH, temperature, repeated use, storage stability, substrate concentration) were determined for immobilized AChE. Lastly, changes in absorbance intensity were measured, and calibration graphs were plotted that reflect the inhibition reaction of immobilized AChE with diclofop-methyl. The inhibition interaction of the enzyme immobilized to the Pt(II) ion containing dendrimers was higher than that of the Pt(IV) ion containing dendrimers.


Keywords


Ferrocene, dendrimers, diclofopmethyl, acetylcholinesterase, immobilization

Full Text:

PDF

References


J. M. Frechet, C. J. Hawker, K. L. Wooley, The convergent route to globular dendritic macromolecules - a versatile approach to precisely functionalized 3-dimensional polymers and novel block-copolymers, J. Macromol. Sci. Part A Pure Appl. Chem. 31, 1627–1645 (1994).

DOI: https://doi.org/10.1080/10601329408545873

T. Sakthivel, A. T. Florence, Adsorption of amphipathic dendrons on polystyrene nanoparticles, Int. J. Pharm. 254, 23–26 (2003).

DOI: https://doi.org/10.1016/S0378-5173(02)00671-3

J. M. J. Frechet, Functional polymers and dendrimers: Reactivity, molecular architecture, and interfacial energy, Science, 263, 1710–1715 (1994).

DOI: https://doi.org/10.1126/science.8134834

U. Boas, J. B. Christensen, P. M. H. Heegaard, Dendrimers: Design, synthesis and chemical properties, J. Mater. Chem. 16, 3785–3798 (2006).

DOI: https://doi.org/10.1039/B611813P

F. N. Crespilho, M. E. Ghica, M. Florescu, F. C. Nart, O. N. Oliveira Jr, C. M. A. Brett, Strategy for enzyme ımmobilization on layer-by-layer dendrimer–gold nanoparticle electrocatalytic membrane incorporating redox mediator, Electrochem. Commun. 8, 1665–1670 (2006). DOI: https://doi.org/10.1016/j.elecom.2006.07.032

L. Svobodova, M. Snejdarkova, T. Hianik, Properties of glucose biosensors based on dendrimer layers. Effect of enzyme ımmobilization, Anal. Bioanal. Chem. 373, 735–741 (2002).

DOI: https://doi.org/10.1007/s00216-002-1419-3

G. R. Newkome, E. He, C. N. Moorefield, Suprasupermolecules with novel properties: Metallodendrimers, Chem. Rev. 99, 1689–1746 (1999), DOI: https://doi.org/10.1021/cr9800659

C. M. Casado, I. Cuadrado, M. Morán, B. Alonso, B. García, B. González, J. Losada, Redoxactive ferrocenyl dendrimers and polymers in solution and immobilised on electrode surfaces, Coord. Chem. Rev. 185, 53–79 (1999). DOI: https://doi.org/10.1016/S0010-8545(98)00252-5

E. Peris, From long-chain conjugated oligomers to dendrimers: Synthesis and physical properties of phenyl-ethenyl-ferrocenyl containing one- and two-dimensional complexes, Coord. Chem. Rev. 248, 279–297 (2004). DOI: https://doi.org/10.1016/j.ccr.2004.01.006

J. H. Lee, Y. D. Han, S. Y. Song, T. D. Kim, H. C. Yoon, Biosensor for organophosphorus pesticides based on the acetylcholine esterase inhibition mediated by choline oxidase bioelectrocatalysis, Bio. Chip. J. 4, 223–229 (2010).

DOI: https://doi.org/10.1007/s13206-010-4310-x

P. Nicolopoulou-Stamati, S. Maipas, C. Kotampasi, P. Stamatis, L. Hens, Chemical pesticides and human health: the urgent need for a new concept in agriculture, Front. Public Health, 4, 1–8 (2016).

DOI: https://doi.org/10.3389/fpubh.2016.00148

U. Blaznik, A. Yngve, I. Erzen, C. Hlastan Ribic, Consumption of fruits and vegetables and probabilistic assessment of the cumulative acute exposure to organophosphorus and carbamate pesticides of schoolchildren in Slovenia, Public Health Nutr. 19, 557–563, (2016).

DOI: https://doi.org/10.1017/S1368980015001494

Md. W. Aktar, D. Sengupta, A. Chowdhury, Impact of pesticides use in agriculture: their benefits and haz-ards, Interdiscip. Toxicol. 2(1), 1–12 (2009).

DOI: https://doi.org/10.2478/v10102-009-0001-7

E. Hasanoğlu Özkan, N. Kurnaz Yetim, H. Tümtürk, N. Sarı, Immobilization of acetylcholinesterase on Pt(II) and Pt(IV) attached nanoparticles for the determination of pesticides, Dalton Trans. 44, 16865–16872 (2015).

DOI: https://doi.org/10.1039/C5DT03004H

M. E. I. Badawy, A. F. El-Aswad, Bioactive paper sensor based on the acetylcholinesterase for the rapid detection of organophosphate and carbamate pesticides, Int. J. Anal. Chem. 2014, 1–8 (2014).

DOI: https://doi.org/10.1155/2014/536823

P. Skládal, Detection of organophosphate and carbamate pesticides using disposable biosensors based on chemically modified electrodes and ımmobilized cholinesterase, Anal. Chim. Acta, 269, 281–287 (1992). DOI: https://doi.org/10.1016/0003-2670(92)85414-2

W. Liu, Z. Chen, H. Xu, Y Shi, Y. Chen, Determina-tion of diclofop-methyl and diclofop residues in soil and crops by gas chromatography, J. Chromatogr. 541, 509–515 (1991).

DOI: https://doi.org/10.1016/S0021-9673(01)88681-7

G. Özhan, S. Özden, B. Alpertunga, Determination of commonly used herbicides in surface water using sol-id-phase extraction and dual-column HPLC-DAD, J. Environ. Sci. Health., Part B, 40, 827–840 (2005).

DOI: https://doi.org/10.1080/03601230500227517

S. Baali, S. Zougar, R. Kherrat, Z. Djeghaba, F. Be-namia, N. Jaffrezic-Renault, Electrochemical charac-terization of enzymatic impedimetric biosensor des-tined to detect organochlorine pesticide: The diclofop-methyl, Sens. Transducers, 149, 135–142 (2013).

N. Kurnaz Yetim, N. Sarı, Novel dendrimers containing redox mediator: Enzyme immobilization and applications, J. Mol. Struct. 1191, 158–164 (2019).

DOI: https://doi.org/10.1016/j.molstruc.2019.04.090

N. Kurnaz Yetim, Synthesis of new Pt(II), Pt(IV) dendrimers containing ferrocene and immobilization usage, Ph.D. Thesis, Gazi University Graduate School of Natural and Applied Sciences, Ankara, Turkey, 2016.

G. L. Ellman, K. D. Courtney, V. Andres R. M. A. Featherstone, New and rapid colorimetric determination of acetylcholinesterase activity, Bio-chem. Pharmacol. 7, 88–95 (1961).

DOI: https://doi.org/10.1016/0006-2952(61)90145-9

W. J. Geary, The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coord. Chem. Rev. 7, 81–122 (1970).

DOI: https://doi.org/10.1016/S0010-8545(00)80009-0

M. Şenel, C. Nergiz, E. Çevik, Novel reagentless glucose biosensor based on ferrocene cored asymmetric PAMAM dendrimers, Sensor. Actuat. B-Chem. 176, 299–306 (2013).

DOI: https://doi.org/10.1016/j.snb.2012.10.072

Ş. Uysal, İ. Uçan, The synthesis and characterization of melamine based Schiff bases and its trinuclear [salen/salophenFe(III)] and [salen/salophenCr(III)] capped complexes, J. Inclusion Phenom. Macrocyclic Chem. 65, 299–304 (2009).

DOI: https://doi.org/10.1007/s10847-009-9581-2

R. Trivedi, S. B. Deepthi, L. Giribabu, B. Sridhar, P. Sujitha, C. G. Kumar, K. V. S. Ramakrishna, Synthesis, crystal structure, electronic spectroscopy, electrochemistry and biological studies of carbohydrate containing ferrocene amides, Appl. Or-ganomet. Chem. 26, 369–376 (2012).

DOI: https://doi.org/10.1002/aoc.2874

N. Kurnaz Yetim, E. Hasanoğlu Özkan, B. Danış, H. Tümtürk, N. Sarı, Research on the repeated use of novel ferrocene-tagged nanomaterial for determination of glucose, Int. J. Polym. Mater. 64, 888–893 (2015).

DOI: https://doi.org/10.1080/00914037.2015.1030659

E. Hasanoğlu Özkan, N. Kurnaz Yetim, M. Gümüş, N. Sarı, A. Dişli, Efficient determination and pesticide control by means of immobilization of acetyl–cholinesterase, Maced. J. Chem. Chem. Eng. 36 (1), 119–128 (2017).

DOI: https://doi.org/10.20450/mjcce.2017.1178

X. Wang, J. Li, H. Xing, S. Xu, Review of toxicology of atrazine and chlorpyrifos on fish, J. Northeast Agric. Univ. 18 (4), 88–92 (2011).

DOI: https://doi.org/10.1016/S1006-8104(12)60031-2

K. E. Larsen, A. L. Lifschitz, C. E. Lanusse, G. L. Virkel, The herbicide glyphosate is a weak ınhibitor of acetylcholinesterase in rats, Environ. Toxicol. Phar-macol. 45, 41–44 (2016).

DOI: https://doi.org/10.1016/j.etap.2016.05.012




DOI: http://dx.doi.org/10.20450/mjcce.2019.1878

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 NURDAN KURNAZ YETİM, NURŞEN SARI

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.