Abstract
Ferrocene (Fc)-containing imidazolium type ionic liquids (ILs) and corresponding poly(ionic liquid) (PIL) membranes with tunable antibacterial activity based on electrochemical redox reaction and host-guest chemistry were developed. The effect of Fc moiety on the antimicrobial activities against both Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli) was studied by minimum inhibitory concentration (MIC). The presence of Fc groups highly enhanced the antibacterial efficiency of Fccontaining ILs because of the generation of reactive oxygen species (ROS). The electrochemical oxidation of Fc to Fc+ and the formation of inclusion complexes between Fc and β-CD via host-guest interactions decreased the antibacterial activities of ILs and PIL membranes. The antibacterial activities may be recovered in some extent upon the electrochemical reduction of Fc+ to Fc or the exclusion of the Fc out of the cavity of β-CD. Furthermore, all the Fc-containing PIL membranes showed relatively low hemolysis activities and none cytotoxicity toward human cells, indicating clinical feasibility in topical applications.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Ng VWL, Ke X, Lee ALZ, Hedrick JL, Yang YY. Adv Mater, 2013, 25: 6730–6736
Tao WX, Zhu MH, Deng ZX, Sun YH. Sci China Chem, 2013, 56: 1364–1371
Miller AJM, Heinekey DM, Mayer JM, Goldberg KI. Angew Chem Int Ed, 2013, 52: 3981–3984
Sun Y, Sun G. Macromolecules, 2002, 35: 8909–8912
Jin JY, Ouyang XY, Li JS, Jiang JH, Wang H, Wang YX, Yang RH. Sci China Chem, 2011, 54: 1266–1272
Shah P, Yue Q, Zhu X, Xu F, Wang HS, Li CZ. Sci China Chem, 2015, 58: 1600–1604
Qin J, Guo J, Xu Q, Zheng Z, Mao H, Yan F. ACS Appl Mater Interfaces, 2017, 9: 10504–10511
Zheng Z, Xu Q, Guo J, Qin J, Mao H, Wang B, Yan F. ACS Appl Mater Interfaces, 2016, 8: 12684–12692
Cui H, Yuan L, Lin L. Carbohydr Polymers, 2017, 177: 156–164
Zhang J, He X, Zhang P, Ma Y, Ding Y, Wang Z, Zhang Z. Sci China Chem, 2015, 58: 761–767
Long Y, Wang Y, Liu Y, Zeng Q, Li Y. Sci China Chem, 2015, 58: 666–672
Wang L, Su B, Cheng C, Ma L, Li S, Nie S, Zhao C. J Mater Chem B, 2014, 3: 1391–1404
Yang Z, Yu H, Zhang L, Wei H, Xiao Y, Chen L, Guo H. Chem Asian J, 2014, 9: 313–318
Sundararaman M, Rajesh Kumar R, Venkatesan P, Ilangovan A. J Med Microbiol, 2013, 62: 241–248
Huang Y, Pappas HC, Zhang L, Wang S, Cai R, Tan W, Wang S, Whitten DG, Schanze KS. Chem Mater, 2017, 29: 6389–6395
Chait R, Craney A, Kishony R. Nature, 2007, 446: 668–671
Zhang Q, Lambert G, Liao D, Kim H, Robin K, Tung C, Pourmand N, Austin RH. Science, 2011, 333: 1764–1767
Huang Z, Zhang H, Bai H, Bai Y, Wang S, Zhang X. ACS Macro Lett, 2016, 5: 1109–1113
Bai H, Zhang H, Hu R, Chen H, Lv F, Liu L, Wang S. Langmuir, 2017, 33: 1116–1120
Bai H, Fu X, Huang Z, Lv F, Liu L, Zhang X, Wang S. Chemistryselect, 2017, 2: 7940–7945
Bai H, Yuan H, Nie C, Wang B, Lv F, Liu L, Wang S. Angew Chem Int Ed, 2015, 54: 13208–13213
Wei T, Zhan W, Cao L, Hu C, Qu Y, Yu Q, Chen H. ACS Appl Mater Interfaces, 2016, 8: 30048–30057
Subianto S, Mistry MK, Choudhury NR, Dutta NK, Knott R. ACS Appl Mater Interfaces, 2009, 1: 1173–1182
Mehta MJ, Kumar A. Chem Asian J, 2017, 12: 3150–3155
Chin W, Yang C, Ng VWL, Huang Y, Cheng J, Tong YW, Coady DJ, Fan W, Hedrick JL, Yang YY. Macromolecules, 2013, 46: 8797–8807
Szente L, Puskás I, Csabai K, Fenyvesi É. Chem Asian J, 2014, 9: 1365–1372
Sun Z, Liu X, Guo J, Xu D, Shen S, Yan F. Chem Asian J, 2017, 12: 2950–2955
Wang XC, Wu JY, Zhou HP, Tian YP, Li L, Yang JX, Jin BK, Zhang SY. Sci China Ser B-Chem, 2009, 52: 930–936
Li SH, Wu CY, Lv XY, Tang X, Zhao XQ, Yan H, Jiang H, Wang XM. Sci China Chem, 2012, 55: 2388–2395
Li SH, Wu CY, Tang X, Gao SP, Zhao XQ, Yan H, Wang XM. Sci China Chem, 2013, 56: 595–603
Xu G, Pranantyo D, Xu L, Neoh KG, Kang ET, Teo SLM. Ind Eng Chem Res, 2016, 55: 10906–10915
Lewandowski EM, Szczupak Ł, Wong S, Skiba J, Guśpiel A, Solecka J, Vrček V, Kowalski K, Chen Y. Organometallics, 2017, 36: 1673–1676
Savjani KT, Gajjar AK, Savjani JK. ISRN Pharm, 2012, 2012: 1–10
Chaudhary VB, Patel JK. Int J Pharm Sci Res, 2013, 4: 68–76
Kumar S, Bhargava D, Thakkar A, Arora S. Crit Rev Ther Drug Carrier Syst, 2013, 30: 217–256
Svenson S, Chauhan AS. Nanomedicine, 2008, 3: 679–702
Yuan C, Guo J, Tan M, Guo M, Qiu L, Yan F. ACS Macro Lett, 2014, 3: 271–275
Cao D, Liu W, Wei X, Xu F, Cui L, Cao Y. Tissue Eng, 2006, 12: 1369–1377
Locock KES, Michl TD, Stevens N, Hayball JD, Vasilev K, Postma A, Griesser HJ, Meagher L, Haeussler M. ACS Macro Lett, 2014, 3: 319–323
Pu F, Liu X, Xu B, Ren J, Qu X. Chem Eur J, 2012, 18: 4322–4328
Li P, Zhou C, Rayatpisheh S, Ye K, Poon YF, Hammond PT, Duan H, Chan-Park MB. Adv Mater, 2012, 24: 4130–4137
Gabriel GJ, Som A, Madkour AE, Eren T, Tew GN. Mater Sci Eng-RRep, 2007, 57: 28–64
Fischer W. Med Microbiol Immunol, 1994, 183: 61–76
Patra M, Gasser G, Wenzel M, Merz K, Bandow JE, Metzler-Nolte N. Organometallics, 2010, 29: 4312–4319
Beveridge TJ. J Bacteriol, 1999, 181: 4725–4733
Palermo EF, Sovadinova I, Kuroda K. Biomacromolecules, 2009, 10: 3098–3107
Acevedo-Morantes CY, Melendez E, Singh SP, Ramirez-Vick JE. J Cancer Sci Ther, 2012, 4: 271–275
Nakahata M, Takashima Y, Yamaguchi H, Harada A. Nat Commun, 2011, 2: 511
Lin B, Qiu L, Lu J, Yan F. Chem Mater, 2010, 22: 6718–6725
Nederberg F, Zhang Y, Tan JPK, Xu K, Wang H, Yang C, Gao S, Guo XD, Fukushima K, Li L, Hedrick JL, Yang YY. Nat Chem, 2011, 3: 409–414
Acknowledgements
This work was supported by the National Science Foundation for Distinguished Young Scholars (21425417), the National Natural Science Foundation of China (21704071), the Jiangsu Province Science Foundation for Youth (BK20170332), General Program Foundation of Jiangsu Province University Science Research Project (17KJB150033), General Program Foundation of Shanghai Municipal Commission of Health and Family Planning (201740107), and the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, and Science and Technology Innovation Fund Project of Zhongshan Hospital, Fudan University (2017ZSCX03).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Zhang, T., Guo, J., Ding, Y. et al. Redox-responsive ferrocene-containing poly(ionic liquid)s for antibacterial applications. Sci. China Chem. 62, 95–104 (2019). https://doi.org/10.1007/s11426-018-9348-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-018-9348-5