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Cyclodextrin-based hyperbranched polyester: synthesis, characterization, and antimicrobial activity

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Abstract

In this study, the synthesis of cyclodextrin-based hyperbranched polyester (CD-based HBPE) was prepared by a simple condensation route via acid chloride approach (Scheme 1). The formation of ester linkages in CD-based HBPE was clearly identified from FTIR and NMR spectroscopy. The resulting structure and the molecular weight of the CD-based HBPE were confirmed with LC–MS analysis. The CD-based HBPE displayed the fluorescence maxima in the 425 nm range with relatively narrow peak widths indicating that they had pure and intense fluorescence. The antimicrobial activity of the CD-based HBPE was evaluated against the Gram-negative organisms like Escherichia coli and Salmonella paratyphi, Gram-positive organisms as Bacillus subtilis and Staphylococcus aureus and fungi such as Aspergillus niger, and Candida albicans. CD-based HBPE showed a great inhibitory effect toward both bacteria and fungi. The microorganism which possess greater antimicrobial activity with standard antibiotics was selected for determining the minimum inhibitory concentration (MIC) value of the CD-based HBPE. Therefore, the MIC value of the CD-based HBPE against B. subtilis was tested and found to be 31.25 μg mL−1. Hence, it is suggested that CD-based HBPE holds good agreement with the antimicrobial assay.

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Scheme 1
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References

  1. Qian, L, Guan, Y, Ziaee, Z, He, B, Zheng, A, Xiao, H, “Rendering Cellulose Fibers Antimicrobial Using Cationic β-Cyclodextrin-Based Polymers Included with Antibiotics.” Cellulose, 16 309–317 (2009)

    Article  Google Scholar 

  2. Rong, L, Jianfeng, D, Qianyuan, J, Jing, L, Zhiwei, X, Jie, L, Xuehong, R, “Preparation and Antimicrobial Activity of β-Cyclodextrin Derivative Copolymers/Cellulose Acetate Nanofibers.” Chem. Eng. J., 248 264–272 (2014)

    Article  Google Scholar 

  3. Chao, D, Ying, Y, Liying, Q, Guanglei, Z, Beihai, H, Huining, X, “Antibacterial Modification of Cellulose Fibers by Grafting β-Cyclodextrin and Inclusion with Ciprofloxacin.” Cellulose, 21 1921–1932 (2014)

    Article  Google Scholar 

  4. Zeynep, A, Sema, YD, Turgay, T, Tamer, U, “Release and Antibacterial Activity of Allylisothiocyanate/β-Cyclodextrin Complex Encapsulated in Electrospun Nanofibers.” Colloid Surface B, 120 25 (2014)

    Google Scholar 

  5. Martin Del Valle, EM, “Cyclodextrins and Their Uses: A Review.” Process Biochem., 39 1033–1046 (2014)

    Article  Google Scholar 

  6. Jozsef, S, “Introduction and General Overview of Cyclodextrin Chemistry.” Chem. Rev., 98 1743–1753 (1988)

    Google Scholar 

  7. Allan, RH, “Industrial Applications of Cyclodextrins.” Chem. Rev., 98 2035–2044 (1998)

    Article  Google Scholar 

  8. Veronique, W, Anne-Magali, L, Dominique, H, Catherine, A, “Cyclodextrin Polymer Nanoassemblies: Strategies for Stability Improvement.” Biomacromolecules, 13 528–534 (2012)

    Article  Google Scholar 

  9. Olga, J, Adam, M, Rebecca, S, Helmut, R, “Cyclodextrin-Modified Polyesters from Lactones and from Bacteria: An Approach to New Drug Carrier Systems.” Macromolecules, 44 1365–1371 (2011)

    Article  Google Scholar 

  10. Wei, T, Xiaodong, F, Jie, K, Tao, L, Yuyang, L, Yi, H, Shengjie, W, Guobin, Z, “Cyclodextrin-Based Hyperbranched Polymers: Molecule Design, Synthesis, and Characterization.” Macromolecules, 42 640–651 (2009)

    Article  Google Scholar 

  11. Qian, L, Guan, Y, Xiao, H, “Preparation and Characterization of Inclusion Complexes of a Cationic β-Cyclodextrin Polymer with Butylparaben or Triclosan.” Int. J. Pharm., 357 244–251 (2008)

    Article  Google Scholar 

  12. Akira, H, Masaoki, F, Shun-ichi, N, “Cooperative Binding by Cyclodextrin Dimers.” Polym. J., 12 29–33 (1980)

    Article  Google Scholar 

  13. Akira, H, Masaoki, F, Shun-ichi, N, “Inclusion of Aromatic Compounds by a β-Cyclodextrin-Epichlorohydrin Polymer.” Polym. J., 13 777–781 (1981)

    Article  Google Scholar 

  14. Jianshu, L, Huining, X, Jiehua, L, YinPing, Z, “Drug Carrier Systems based on Water-Soluble Cationic β-Cyclodextrin Polymers.” Int. J. Pharm., 278 329–342 (2004)

    Article  Google Scholar 

  15. Makvandi, P, Ghaemy, M, Ghadiri, AA, Mohseni, M, “Photocurable, “Antimicrobial Quaternary Ammonium–modified Nanosilica.” J. Dent. Res., 94 140–146 (2015)

    Article  Google Scholar 

  16. Clinical and Laboratory Standards Institute, “Method for Antifungal Disk Diffusion Susceptibility Testing of Yeasts.” Approved Guidelines—second edition. (2009). http://shop.clsi.org/site/Sample_pdf/M44A2_sample.pdf. Accessed 28 Aug 2009

  17. Prudencio, A, Schmeltzer, RC, Uhrich, KE, “Effect of Linker Structure on Salicylic Acid-Derived Poly(anhydride-esters).” Macromolecules, 38 6895–6901 (2005)

    Article  Google Scholar 

  18. Thiyagarjan, S, Sivakumar, C, Sultan, N, “Hydroxyl-Terminated Hyperbranched Aromatic Poly(ether-ester)s: Synthesis, Characterization, End-Group Modification, and Optical Properties.” J. Polym. Sci. Pol. Chem., 46 5414–5430 (2008)

    Article  Google Scholar 

  19. Sivakumar, C, Sultan, N, “Hydroxyl- and Amine-Terminated Hyperbranched Polyurethanes Using AB2-Type Azide Monomers: Synthesis, Characterization, Fluorescence, and Charge-Transfer Complexation Studies.” J. Polym. Sci. Polym. Chem., 47 3337–3351 (2009)

    Article  Google Scholar 

  20. Chen, JW, Peng, H, Law, CW, Dong, YP, Lam, JWY, Williams, ID, Tang, BZ, “Hyperbranched Poly(phenylenesilolene)s: Synthesis, Thermal Stability, Electronic Conjugation, Optical Power Limiting, and Cooling-Enhanced Light Emission.” Macromolecules, 36 4319–4327 (2003)

    Article  Google Scholar 

  21. Peng, H, Cheng, L, Luo, J, Xu, K, Sun, Q, Dong, Y, Salhi, F, Lee, PPS, Chen, J, Tang, BZ, “Simple Synthesis, Outstanding Thermal Stability, and Tunable Light-Emitting and Optical-Limiting Properties of Functional Hyperbranched Polyarylene.” Macromolecules, 35 5349–5351 (2002)

    Article  Google Scholar 

  22. Jenekhe, SA, Osaheni, JA, “Excimers and Exciplexes of Conjugated Polymers.” Science, 265 765–768 (1994)

    Article  Google Scholar 

  23. Xianzhen, L, Wenjin, Z, Yong, Z, Qioong, H, Wei, Y, Yong, C, “Synthesis and Properties of Novel Poly(p-phenylenevinylene) Copolymers for Near-Infrared Emitting Diodes.” Eur. Polym. J., 41 2923–2933 (2005)

    Article  Google Scholar 

  24. Ye, Y, Ren, H, Zhu, S, Tan, H, Li, X, Li, D, Mu, C, “Synthesis of Oxidized β-Cyclodextrin with High Aqueous Solubility and Broad-Spectrum Antimicrobial Activity.” Carbohydr. Polym., 177 97–104 (2017)

    Article  Google Scholar 

  25. Karpagam, S, Guhanathan, S, “Phosphorus Based Indole and Imidazole Functionalized Hyperbranched Polyester as Antimicrobial Surface Coating Materials.” Prog. Org. Coat., 77 1901–1910 (2014)

    Article  Google Scholar 

  26. Kenawy, ER, Worley, SD, Broughton, R, “The Chemistry and Applications of Antimicrobial Polymers: A State-of-the-Art Review.” Biomacromolecules, 8 1359–1384 (2007)

    Article  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the Sri Krishna College of Technology and Bharathiar University for their constant support.

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Correspondence to Chickiyan Sivakumar.

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Supplementary material 1 (PDF 584 kb)

Supplementary material 2 (PDF 214 kb)

Fig. S1 LC–MS spectra of (a) acyl terminated HBPE and (b) CD-based HBPE (EPS 795 kb)

Fig. S2 MIC Test of CD-based HBPE against B. Subtilis (EPS 615 kb)

11998_2017_41_MOESM5_ESM.eps

Fig. S3 Cyclic voltammograms of the CD-based HBPE in toluene/acetonitrile (v/v 8:2) containing 0.1 M TBAP at a scan rate of 10 mV/s, vs Ag/AgCl (EPS 730 kb)

Fig. S4 FTIR spectrum of HBPE (EPS 1101 kb)

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Prabu, S., Sivakumar, C. Cyclodextrin-based hyperbranched polyester: synthesis, characterization, and antimicrobial activity. J Coat Technol Res 15, 1059–1066 (2018). https://doi.org/10.1007/s11998-017-0041-4

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