Fabrication of Molecularly Imprinted Electrospun Nanofibers with Mono-amidoxime Functional Ligand for Efficient Decontamination of Toxic Organophosphates

Lan Wang; Peng Jiang; Ya-Lin Niu; Jun-Peng Cao; Tian-Ying Guo

doi:10.1007/s10118-024-3075-y

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Fabrication of Molecularly Imprinted Electrospun Nanofibers with Mono-amidoxime Functional Ligand for Efficient Decontamination of Toxic Organophosphates

RESEARCH ARTICLE | Updated：2024-03-14

- Fabrication of Molecularly Imprinted Electrospun Nanofibers with Mono-amidoxime Functional Ligand for Efficient Decontamination of Toxic Organophosphates
- Chinese Journal of Polymer Science Vol. 42, Issue 4, Pages: 446-456(2024)
- Affiliations：
  
  Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry and Frontier Science Center for the Creation of New Organic Substances, Nankai University, Tianjin 300071, China
- Author bio：
  
  tyguo@nankai.edu.cn
- Funds：
- DOI：10.1007/s10118-024-3075-y
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Wang, L.; Jiang, P.; Niu, Y. L.; Cao, J. P.; Guo, T. Y. Fabrication of molecularly imprinted electrospun nanofibers with mono-amidoxime functional ligand for efficient decontamination of toxic organophosphates. Chinese J. Polym. Sci. 2024, 42, 446–456

Lan Wang, Peng Jiang, Ya-Lin Niu, et al. Fabrication of Molecularly Imprinted Electrospun Nanofibers with Mono-amidoxime Functional Ligand for Efficient Decontamination of Toxic Organophosphates. [J]. Chinese Journal of Polymer Science 42(4):446-456(2024)
Wang, L.; Jiang, P.; Niu, Y. L.; Cao, J. P.; Guo, T. Y. Fabrication of molecularly imprinted electrospun nanofibers with mono-amidoxime functional ligand for efficient decontamination of toxic organophosphates. Chinese J. Polym. Sci. 2024, 42, 446–456 DOI： 10.1007/s10118-024-3075-y.

Lan Wang, Peng Jiang, Ya-Lin Niu, et al. Fabrication of Molecularly Imprinted Electrospun Nanofibers with Mono-amidoxime Functional Ligand for Efficient Decontamination of Toxic Organophosphates. [J]. Chinese Journal of Polymer Science 42(4):446-456(2024) DOI： 10.1007/s10118-024-3075-y.

摘要

A novel post molecular imprinting method to prepare molecularly imprinted electrospun nanofiber with stable-binding and densely packed accessible active sites by crosslinking amidoxime side groups chains the surface of amidoxime-based functional polymer/polyacrylonitrile blending electrospun fibers. The resultant MIF-PMAOX/PAN fibers demonstrate the versatility and superiority as self-detoxifying catalyst for organophosphates.

Abstract

There is an urgent imperative to discover practical and efficacious artificial catalysts for the expeditious decontamination of toxic organophosphates. Herein

we propose a novel molecularly imprinted approach utilizing electrospun fiber scaffolds. Specifically

an amidoxime-based functional polymer (PMAOX) has been synthesized

which contains amidoxime groups that can act as nucleophiles and ligands for the formation of catalytic active sites. This polymer was blended with polyacrylonitrile (PAN)

a well-processable material

to prepare a nanofiber mat using electrospinning techniques. Then

the amidoxime side groups on fiber surface were further cross-linked after the molecular coordination of templates to complete the molecularly imprinting process. This approach can not only enhance the content of functional molecularly imprinted polymers without affecting structural stability

but also combines surface MI technology to fully expose and leverage the advantages of active sites. The as prepared molecularly imprinted electrospun nanofibers MIF-Zn-PMAOX/PAN-6/4 catalyzes the degradation of paraoxon with a half-life of 32 min

and MIF-Ag-PMAOX/PAN catalyzes the degradation of parathion with a half-life of 18 min. The maximum catalytic rate evidence rate enhancements nearly 3700-fold of the self-hydrolysis. Thus

the mono-amidoxime based molecularly imprinted fibers demonstrate the versatility and superiority as self-detoxifying for organophosphates.

关键词

Keywords

Organophosphates hydrolysisElectrospinningMolecular imprinting

references

Iqbal, A.; Malik, S.; Nurulain, S. M.; Musilek, K.; Kuca, K.; Kalasz, H.; Fatmi, M. Q. Reactivation potency of two novel oximes (K456 and K733) against paraoxon-inhibited acetyl and butyrylcholinesterase: in silicoand in vitromodels.Chemico-Biological Interactions2019, 310, 108735..

Zhang, L.; Murata, H.; Amitai, G.; Smith, P. N.; Matyjaszewski, K.; Russell, A. J. Catalytic detoxification of organophosphorus nerve agents by butyrylcholinesterase-polymer-oxime bioscavengers.Biomacromolecules2020, 21, 3867−3877..

Su, S.; Jung, D.; Gong, X.; Idrees, K. B.; Hanna, S. L.; Islamoglu, T.; Gianneschi, N. C.; Farha, O. K. Aggregation-suppressed porous processable hexa-zirconium/polymer composites for detoxification of a nerve agent simulant.Chem. Mater.2022, 34, 4983−4991..

Chen, Y.; Luo, Z.; Lu, X. Construction of novel enzyme-graphene oxide catalytic interface with improved enzymatic performance and its assembly mechanism.ACS Appl. Mater. Interfaces2019, 11, 11349−11359..

Hoskin, F. C.; Roush, A. H. Hydrolysis of nerve gas by squid-type diisopropyl phosphorofluoridate hydrolyzing enzyme on agarose resin.Science1982, 215, 1255−7..

Fan, F.; Zheng, Y.; Zhang, Y.; Zheng, H.; Zhong, J.; Cao, Z. A comprehensive understanding of enzymatic degradation of the G-type nerve agent by phosphotriesterase: revised role of water molecules and rate-limiting product release.ACS Catal.2019, 9, 7038−7051..

Luo, H.-B.; Castro, A. J.; Wasson, M. C.; Flores, W.; Farha, O. K.; Liu, Y. Rapid, biomimetic degradation of a nerve agent simulant by incorporating imidazole bases into a metal-organic framework.ACS Catal.2021, 11, 1424−1429..

Jiang, P.; Wang, L.; Li, J.; Liu, W.; Chen, Z.; Guo, T. Facile in-situstrategy for incorporating amphoteric dopamine into metal-organic framework with optimized degradation capacity of nerve agents simulant.Chem. Eng. J.2022, 448, 137702..

Moon, S. Y.; Liu, Y.; Hupp, J. T.; Farha, O. K. Instantaneous hydrolysis of nerve-agent simulants with a six-connected zirconium-based metal-organic framework.Angew. Chem. Int. Ed.2015, 54, 6795−6799..

de Koning, M. C.; van Grol, M.; Breijaert, T. Degradation of paraoxon and the chemical Warfare Agents VX, Tabun, and Soman by the metal-organic frameworks UiO-66-NH2, MOF-808, NU-1000, and PCN-777.Inorg. Chem.2017, 56, 11804−11809..

Ma, K.; Cheung, Y. H.; Kirlikovali, K. O.; Xie, H.; Idrees, K. B.; Wang, X.; Islamoglu, T.; Xin, J. H.; Farha, O. K. Fibrous Zr-MOF nanozyme aerogels with macro-nanoporous structure for enhanced catalytic hydrolysis of organophosphate toxins.Adv. Mater.2023, n/a, 2300951..

Mo, W.; Zhu, Z.; Kong, F.; Li, X.; Chen, Y.; Liu, H.; Cheng, Z.; Ma, H.; Li, B. Controllable synthesis of conjugated microporous polymer films for ultrasensitive detection of chemical warfare agents.Nat. Commun.2022, 13, 5189..

Wang, L.; Jiang, P.; Liu, W.; Li, J.; Chen, Z.; Guo, T. Molecularly imprinted self-buffering double network hydrogel containing bi-amidoxime functional groups for the rapid hydrolysis of organophosphates.J. Hazard. Mater.2023, 444, 130332..

Arifuzzaman, M. D.; Zhao, Y. Artificial zinc enzymes with fine-tuned active sites for highly selective hydrolysis of activated esters.ACS Catal.2018, 8, 8154−8161..

Arifuzzaman, M. D.; Bose, I.; Bahrami, F.; Zhao, Y. Imprinted polymeric nanoparticles as artificial enzymes for ester hydrolysis at room temperature and pH 7.Chem. Catal.2022, 2, 2049−2065..

Li, X.; Zangiabadi, M.; Zhao, Y. Molecularly imprinted synthetic glucosidase for the hydrolysis of cellulose in aqueous andnonaqueous solutions.J. Am. Chem. Soc.2021, 143, 5172−5181..

Zangiabadi, M.; Zhao, Y. Selective binding of complex glycans and glycoproteins in water by molecularly imprinted nanoparticles.Nano Lett.2020, 20, 5106−5110..

Yuan, Y.; Yang, Y.; Faheem, M.; Zou, X.; Ma, X.; Wang, Z.; Meng, Q.; Wang, L.; Zhao, S.; Zhu, G. Molecularly imprinted porous aromatic frameworks serving as porous artificial enzymes.Adv. Mater.2018, 30, 1800069..

Tsai, P. C.; Fan, Y.; Kim, J.; Yang, L.; Almo, S. C.; Gao, Y. Q.; Raushel, F. M. Structural determinants for the stereoselective hydrolysis of chiral substrates by phosphotriesterase.Biochemistry2010, 49, 7988−7997..

Prokop, Z.; Oplustil, F.; DeFrank, J.; Damborsky, J. Enzymes fight chemical weapons.Biotechnol. J.2006, 1, 1370−80..

Kirlikovali, K. O.; Chen, Z.; Islamoglu, T.; Hupp, J. T.; Farha, O. K. Zirconium-based metal-organic frameworks for the catalytic hydrolysis of organophosphorus nerve agents.ACS Appl. Mater. Interfaces2020, 12, 14702−14720..

Bigley, A. N.; Raushel, F. M. Catalytic mechanisms for phosphotriesterases.Biochim. Biophys. Acta2013, 1834, 443−53..

Yang, M.-Y.; Iranzo, O.; Richard, J. P.; Morrow, J. R. Solvent deuterium isotope effects on phosphodiester cleavage catalyzed by an extraordinarily active Zn(II) complex.J. Am. Chem. Soc.2005, 127, 1064−1065..

Shu, J.; Yue, J.; Qiu, X.; Liu, X.; Ren, W.; Li, Q.; Li, Y.; Xu, B.; Zhang, K.; Jiang, W. Binuclear metal complexes with a novel hexadentate imidazole derivative for the cleavage of phosphate diesters and biomolecules: distinguishable mechanisms.Inorg. Chem. Front.2021, 8, 2684−2696..

Tirel, E. Y.; Bellamy, Z.; Adams, H.; Lebrun, V.; Duarte, F.; Williams, N. H. Catalytic zinc complexes for phosphate diester hydrolysis.Angew. Chem. Int. Ed.2014, 53, 8246−8250..

Pan, J.; Liu, S.; Jia, H.; Yang, J.; Qin, M.; Zhou, T.; Chen, Z.; Jia, X.; Guo, T. Rapid hydrolysis of nerve agent simulants by molecularly imprinted porous crosslinked polymer incorporating mononuclear zinc(II)-picolinamine-amidoxime module.J. Catal.2019, 380, 83−90..

Zheng, S.; Pan, J.; Wang, J.; Liu, S.; Zhou, T.; Wang, L.; Jia, H.; Chen, Z.; Peng, Q.; Guo, T. Ag(I)pyridine-amidoxime complex as the catalysis activity domain for the rapid hydrolysis of organothiophosphate-based nerve agents: mechanistic evaluation and application.ACS Appl. Mater. Interfaces2021, 13, 34428−34437..

Gibson, P.; Schreuder-Gibson, H.; Rivin, D. Transport properties of porous membranes based on electrospun nanofibers.Colloids and Surfaces A: Physicochem. Engin. Aspects 2001, 187−188, 469-481..

Chen, L.; Bromberg, L.; Lee, J. A.; Zhang, H.; Schreuder-Gibson, H.; Gibson, P.; Walker, J.; Hammond, P. T.; Hatton, T. A.; Rutledge, G. C. Multifunctional electrospun fabrics vialayer-by-layer electrostatic assembly for chemical and biological protection.Chem. Mater.2010, 22, 1429−1436..

Wu, K.; Zhang, X.; Yang, W.; Liu, X.; Jiao, Y.; Zhou, C. Influence of layer-by-layer assembled electrospun poly(l-lactic acid) nanofiber mats on the bioactivity of endothelial cells.Appl. Surf. Sci.2016, 390, 838−846..

McCarthy, D. L.; Liu, J.; Dwyer, D. B.; Troiano, J. L.; Boyer, S. M.; DeCoste, J. B.; Bernier, W. E.; Jones, J. W. E. Electrospun metal-organic framework polymer composites for the catalytic degradation of methyl paraoxon.New J. Chem.2017, 41, 8748−8753..

Lu, A. X.; McEntee, M.; Browe, M. A.; Hall, M. G.; DeCoste, J. B.; Peterson, G. W. MOFabric: electrospun nanofiber mats from PVDF/UiO-66-NH2for chemical protection and decontamination.ACS Appl. Mater. Interfaces2017, 9, 13632−13636..

Zhang, L.; Guo, Y.; Chi, W. H.; Shi, H. G.; Ren, H. Q.; Guo, T. Y. Electrospun nanofibers containing p-nitrophenol imprinted nanoparticles for the hydrolysis of paraoxon.Chinese J. Polym. Sci.2014, 32, 1469−1478..

Moraes Segundo, J. d. D. P. d.; Oneide Silva de Moraes, M.; Brito, W. R.; d'Ávila, M. A. Incorporation of molecularly imprinted polymer nanoparticles in electrospun polycaprolactone fibers.Mater. Lett.2020, 275, 128088..

Perez-Puyana, V.; Wieringa, P.; Guerrero, A.; Romero, A.; Moroni, L. (Macro)Molecular Imprinting of Proteins on PCL Electrospun Scaffolds.ACS Appl. Mater. Interfaces2021, 13, 29293−29302..

Wu, K.; Yang, W.; Jiao, Y.; Zhou, C. A surface molecularly imprinted electrospun polyethersulfone (PES) fiber mat for selective removal of bilirubin.J. Mater. Chem. B2017, 5, 5763−5773..

Ma, X.; Lin, H.; He, Y.; She, Y.; Wang, M.; Abd El-Aty, A. M.; Afifi, N. A.; Han, J.; Zhou, X.; Wang, J.; Zhang, J. Magnetic molecularly imprinted polymers doped with graphene oxide for the selective recognition and extraction of four flavonoids from Rhododendron species.J. Chromatography A2019, 1598, 39−48..

Devic, T.; Serre, C. High valence 3p and transition metal based MOFs.Chem. Soc. Rev.2014, 43, 6097−6115..

Mian, M. R.; Chen, H.; Cao, R.; Kirlikovali, K. O.; Snurr, R. Q.; Islamoglu, T.; Farha, O. K. Insights into catalytic hydrolysis of organophosphonates at M–OH sites of azolate-based metal organic frameworks.J. Am. Chem. Soc.2021, 143, 9893−9900..

Chen, J. Q.; Zheng, Q. Q.; Xiao, S. J.; Zhang, L.; Liang, R. P.; Ouyang, G.; Qiu, J. D. Construction of two-dimensional fluorescent covalent organic framework nanosheets for the detection and removal of nitrophenols.Anal. Chem.2022, 94, 2517−2526..

Soorya, V. C.; Berchmans, S. Flower like Bi structures on Pt surface facilitating effective cholesterol biosensing.Mater. Sci. Eng. C2016, 64, 183−189..

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