Self-assembly of artificial peroxidase mimics from alternating copolymers with chromogenic and biocatalyst potentialities

Tahir Rasheed; Faran Nabeel; Muhammad Bilal

Journal of Industrial and Engineering Chemistry, Vol.78, 315-323, October, 2019

DOI10.1016/j.jiec.2019.05.039 Export Citation

Self-assembly of artificial peroxidase mimics from alternating copolymers with chromogenic and biocatalyst potentialities

Tahir Rasheed^†, Faran Nabeel, and Muhammad Bilal¹

School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China
¹School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huaian 223003, China

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Inspiring from the multiple functions and delicate architectures of natural peroxidases, we constructed an artificial peroxidase that can mimic as horseradish peroxidase (HRP). This mimicking construct was engineered by the self-assembly of alternating copolymers followed by encapsulation of hemin resulted in a functional vesicle exhibiting activity like peroxidase. The thiazole moiety present in copolymers poly (ethylene glycol)diglycidyl ether-alt-Bismuth-thiol P(PEGDGE-a-BTT) and 1,7-butadiene-diepoxide-alt- Bismuth-thiol P(BDD-a-BTT) can easily coordinate with hemin molecule. In this complex, hemin is present as a pentacoordinate ligand having an open site for substrate binding similar to the microenvironment in natural peroxidase. The as-prepared functional vesicles exhibited better stability and excellent catalytic activity in oxidizing orange II (azo dye) and phenolic compounds such as catechol and 3, 30 , 5, 50-tetramethylbenzidine (TMB) using hydrogen peroxide (H2O2) as compared to HRP over a wide pH, temperature range, and substrate concentrations. Another striking feature of these functional vesicles (alternating polymer vesicles loaded with hemin) is their use as recognition systems for chromogenic substances, indicating that these vesicles can be used as new biocatalysts for specific functions.

Keywords:Alternating copolymers;Self-assembly;Hemin vesicles;Peroxidase-mimic activity;Chromogenic detection

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[2] Koeller KM, Wong CH, Nature, 409, 232 (2001)

[3] Grcger H, Hummel W, Curr. Opin. Chem. Biol., 19, 171 (2014)

[4] Liese A, Hilterhause L, Chem. Soc. Rev., 42, 6236 (2013)

[5] Wohlgemuth R, Curr. Opin. Biotechnol., 21(6), 713 (2010)

[6] Bilal M, Asgher M, Parra-Saldivar R, Hu H, Wang W, Zhang X, Iqbal HMN, Sci. Total Environ., 576, 646 (2017)

[7] Amin F, Bhatti HN, Bilal M, Asgher M, Int. J. Biol. Macromol., 95, 974 (2017)

[8] Rehman S, Wang P, Bhatti HN, Bilal M, Asgher M, Int. J. Biol. Macromol., 97, 279 (2017)

[9] Lin Y, Ren J, Qu X, Accounts Chem. Res., 47, 1097 (2014)

[10] Breslow R, Chem. Soc. Rev., 1, 553 (1972)

[11] Groger H, Wilken J, Angew. Chem.-Int. Edit., 40, 529 (2001)

[12] Meunier B, Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Imperial College Press, London, 2000.

[13] Motherwell WB, Bingham MJ, Six Y, Tetrahedron, 57, 4663 (2001)

[14] (a) Ji X, Dong S, Wei P, Xia D, Huang F, Adv. Mater. 25, 5725 (2013); (b) Jie K, Zhou Y, Ji X, Polym. Chem. 6, 218 (2015); (c) Ji X, Wang H, Li Y, Xia D, Li H, Tang G, Sessler JL, Huang F, Chem. Sci. 7, 6006 ( 2016); (d) Dong Z, Luo Q, Liu J, Chem. Soc. Rev. 41, 1177 (2012).

[15] Hamid M, Khalil R, Food Chem., 115, 1177 (2009)

[16] Arai T, Ishibashi K, Tomizaki K, Kato T, Nishino N, Tetrahedron, 61, 4023 (2005)

[17] Zhang Y, Xu C, Li B, RSC Adv., 3, 6044 (2013)

[18] Nastri F, Lista L, Ringhieri P, Vitale R, Faiella M, Andreozzi C, Travascio P, Maglio O, Lombardi A, Pavone V, Chem. Eur. J., 17, 4444 (2011)

[19] Zhang F, Long X, Zhang D, Sun Y, Zhou Y, Ma Y, Qi L, Zhang X, Sens. Actuators B-Chem., 192, 150 (2014)

[20] Guo Y, Deng L, Li J, Guo S, Wang E, Dong S, ACS Nano, 5, 1282 (2011)

[21] Xue T, Peng B, Xue M, Zhong X, Chiu C, Yang S, Qu Y, Ruan L, Jiang S, Dubin S, Nat. Commun., 5, 3200 (2014)

[22] Wang Q, Yang Z, Zhang X, Xiao X, Chang CK, Xu B, Angew. Chem.-Int. Edit., 46, 4285 (2007)

[23] Castriciano M, Romeo A, Baratto M, Pogni R, Scolaro L, Chem. Commun., 44, 688 (2008)

[24] Hu P, Han L, Dong S, ACS Appl. Mater. Interfaces, 6, 500 (2014)

[25] Qu R, Shen L, Chai Z, Jing C, Zhang Y, An Y, Shi L, ACS Appl. Mater. Interfaces, 6, 19207 (2014)

[26] Li C, Chen C, Li S, Rasheed T, Huang P, Huang T, Zhang Y, Huang W, Zhou Y, Polym. Chem., 8, 4688 (2017)

[27] Lu Y, Berry SM, Pfister TD, Chem. Rev., 101(10), 3047 (2001)

[28] Moosavi-Movahedi AA, Semsarha F, Heli H, Nazari K, Ghourchian H, Hong J, Hakimelahi GH, Saboury AA, Sefidbakht Y, Colloids Surf. A: Physicochem. Eng. Asp., 320, 213 (2008)

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[30] Watanabe K, Kitagishi H, Kano K, Angew. Chem.-Int. Edit., 52, 6894 (2013)

[31] Ryabova ES, Dikiy A, Hesslein AE, Bjerrum MJ, Ciurli S, Nordlander E, J. Biol. Inorg. Chem., 9, 385 (2004)

[32] Hitomi Y, Hiramatsu K, Arakawa K, Takeyasu T, Hata M, Kodera M, Dalton Trans., 42, 12878 (2013)

[33] Mutambanengwe CCZ, Togo CA, Whiteley CG, Biotechnol. Prog., 23(5), 1095 (2007)

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[36] Sun Y, Gao G, Du G, Cheng Y, Fu J, ACS Macro Lett., 3, 496 (2014)

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[40] Tanner P, Balasubramanian V, Palivan CG, Nano Lett., 13, 2875 (2013)