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Photoregulating Catalytic Activity of Cyclodextrin-Based Artificial Glutathione Peroxidase by Charged Azobenzene

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Abstract

Modulating the activities of enzymes by using an external signal is widely used for many applications. In this paper, it has been performed for the first time that photoregulating the activity of artificial glutathione peroxidase (GPx) by using photocontrolled inclusion–exclusion reaction of the azobenzene with two typical GPx mimics, the telluride β-Cyclodextrin (β-CD) dimmer and the ditelluride β-CD dimmer. The activities of both mimics were differently inhibited by either cationic or anionic azobenzene, owing to the catalytic capacity variance of the telluride moieties of the mimics and the different strength of the electrostatic interactions between the charges of the substrates and the azobenzenes. The inclusion of the anionic azobenzene with the ditelluride β-CD dimmer represented the largest inhibition rate. When the inclusion was irradiated upon UV light, the activity recovered, whereas inhibited again upon visible light. Such process could be repeated many times and a switchable artificial enzyme based on the reaction was proposed.

Graphical Abstract

It was performed that photoregulating artificial enzyme by using photocontroled inclusion-exclusion reaction of one 6-ditellurium β-CD dimmer with two anionic azobenzenes. When inclusion underwent the activity of the artificial enzyme was inhibited. After irradiation with UV light, the cis-isomer azobenzene formed, and went away from the cavity left an appropriate cavity for accommodating a substrate, as a result, the activity recovered. After irradiation with visible light, the activity was inhibited over again, owing to that the trans-isomer azobenzene regenerated, and regressed to the inclusion. Such process could be repeated many times.

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References

  1. Nordberg J, Arner ESJ (2001) Free Radic Bio Med 31:1287

    Article  CAS  Google Scholar 

  2. Arthur J (2000) Cell Mol Life Sci 57:1825

    Article  CAS  Google Scholar 

  3. Toscano MD, Woycechowsky KJ, Hilvert D (2007) Angew Chem Int Ed 46:3212

    Article  CAS  Google Scholar 

  4. Reiter R, Wendel A (1985) Biochem Pharmacol 34:2287

    Article  CAS  Google Scholar 

  5. Mirault ME, Tremblay A, Beaudoin N, Tremblay M (1991) J Biol Chem 266:20752

    CAS  Google Scholar 

  6. Ho YS, Magnenat JL, Bronson RT, Cao J, Gargano M, Sugawara M (1997) J Biol Chem 272:16644

    Article  CAS  Google Scholar 

  7. Dugave C, Demange L (2003) Chem Rev 103:2475

    Article  CAS  Google Scholar 

  8. Tamai N, Miyasaka H (2000) Chem Rev 100:1875

    Article  CAS  Google Scholar 

  9. Ren XJ, Xue Y, Zhang K, Liu JQ, Luo GM, Zheng J, Mu Y, Shen JC (2001) FEBS Lett 507:377

    Article  CAS  Google Scholar 

  10. Dong ZY, Liu JQ, Mao SZ, Huang X, Yang B, Ren XJ, Luo GM, Shen JC (2004) J Am Chem Soc 126:16395

    Article  CAS  Google Scholar 

  11. Dong ZY, Liang K, Wang CY, Huang X, Mao SZ, Li XQ, Xu JY, Liu JQ, Luo GM, Shen JC (2007) J Mol Catal A: Chem 277:193

    Article  CAS  Google Scholar 

  12. Breslow R, Dong SD (1998) Chem Rev 98:1997

    Article  CAS  Google Scholar 

  13. Chen Y, Liu Y (2009) Chem Soc Rev 39:495

    Article  Google Scholar 

  14. Balzani V, Credi A, Raymo FM, Stoddart JF (2000) Angew Chem Int Ed 39:3349

    Google Scholar 

  15. Harada A (2001) Acc Chem Res 34:456

    Article  CAS  Google Scholar 

  16. Kaufman H, Vratsanos SM, Erlanger BF (1968) Science 162:1487

    Article  CAS  Google Scholar 

  17. Willner I, Rubin S (1996) Angew Chem Int Ed 35:367

    Article  CAS  Google Scholar 

  18. Woolley GA (2005) Acc Chem Res 38:486

    Article  CAS  Google Scholar 

  19. Graham CRE-D (2007) Nat Methods 4:619

    Article  Google Scholar 

  20. Ueno A, Takahashi K, Osa T (1980) J Chem Soc, Chem Commun (17):837. doi:10.1039/C39800000837

  21. Ueno A, Takahashi K, Osa T (1981) J Chem Soc, Chem Commun (3):94. doi:10.1039/C39810000094

  22. Lee W-S, Ueno A (2001) Macromol Rapid Commun 22:448

    Article  CAS  Google Scholar 

  23. Fu H, Zhou YH, Chen WL, Deqing ZG, Tong ML, Ji LN, Mao ZW (2006) J Am Chem Soc 128:4924

    Article  CAS  Google Scholar 

  24. Wang YP, Ma N, Wang ZQ, Zhang X (2007) Angew Chem Int Ed 46:2823

    Article  CAS  Google Scholar 

  25. Wu ZP, Hilvert D (1990) J Am Chem Soc 112:5647

    Article  CAS  Google Scholar 

  26. Schneider H, Hacket F, Rudiger V, Ikeda H (1998) Chem Rev 98:1755

    Article  CAS  Google Scholar 

  27. Nepogodiev S, Stoddart J (1998) Chem Rev 98:1959

    Article  CAS  Google Scholar 

  28. Tian H, Wang QC (2006) Chem Soc Rev 35:361

    Article  CAS  Google Scholar 

  29. Wenz G, Han BH, Muller A (2006) Chem Rev 106:782

    Article  CAS  Google Scholar 

  30. Shimizu H, Kaito A, Hatano M (1979) Bull Chem Soc Jpn 52:2678

    Article  CAS  Google Scholar 

  31. Yoshida N, Yamaguchi H, Higashi M (1994) J Chem Soc, Perkin Trans 2(12):2507

    Google Scholar 

  32. Connors K (1997) Chem Rev 97:1325

    Article  CAS  Google Scholar 

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Acknowledgment

Financial support from the Natural Science Foundation of China (No: 20874036, 20921003), the NSFC for Outstanding Younger Scientist (No. 20725415), the 111 project (B06009) and the National Basic Research Program (2007CB808006).

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Authors and Affiliations

  1. State Key Laboratory for Supramolecular Structure and Materials, College of Chemistry, Jilin University, 130012, Changchun, People’s Republic of China

    Ping Wu, Ruiqing Xiao, Chunqiu Zhang, Lipeng Zhou, Quan Luo, Jiayun Xu & Junqiu Liu

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  1. Ping Wu
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  2. Ruiqing Xiao
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  3. Chunqiu Zhang
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  4. Lipeng Zhou
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  7. Junqiu Liu
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Correspondence to Junqiu Liu.

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Wu, P., Xiao, R., Zhang, C. et al. Photoregulating Catalytic Activity of Cyclodextrin-Based Artificial Glutathione Peroxidase by Charged Azobenzene. Catal Lett 138, 62–67 (2010). https://doi.org/10.1007/s10562-010-0363-7

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  • DOI: https://doi.org/10.1007/s10562-010-0363-7

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