Biocidal polymers: synthesis and antimicrobial properties of benzaldehyde derivatives immobilized onto amine-terminated polyacrylonitrile

详细信息    查看全文

• 作者：Abdullah Alamri (1)
  Mohamed H El-Newehy (1) (2)
  Salem S Al-Deyab (1)
  
• 刊名：Chemistry Central Journal
• 出版年：2012
• 出版时间：December 2012
• 年：2012
• 卷：6
• 期：1
• 全文大小：1002KB
• 参考文献：1. Ahmed AEI, Hay JN, Bushell ME, Wardell JN, Cavalli G: Biocidal polymers (I): Preparation and biological activity of some novel biocidal polymers based on uramil and its azo-dyes. / React Funct Polym 2008, 68:248鈥?60. CrossRef
  2. Kenawy E-R, Mahmoud YAG: Biologically active polymers, 6 synthesis and antimicrobial activity of some linear copolymers with quaternary ammonium and phosphonium groups. / Macromol Biosci 2003, 3:107鈥?16. CrossRef
  3. Li G, Shen J: A study of pyridinium-type functional polymers. IV. Behavioral features of the antibacterial activity of insoluble pyridinium-type polymers. / J Appl Polym Sci 2000, 78:676鈥?84. CrossRef
  4. Gabriel GJ, Maegerlein JA, Nelson CF, Dabkowski JM, Eren T, Nsslein K, Tew GN: Comparison of facially amphiphilic versus segregated monomers in the design of antibacterial copolymers. / Chem-Eur. J. 2009, 15:433鈥?39. CrossRef
  5. Madkour AE, Tew GN: Perspective-Towards self-sterilizing medical devices: controlling infection. / Polym. Int. 2008, 57:6鈥?0. CrossRef
  6. Gabriel GJ, Som A, Madkour AE, Eren T, Tew GN: Infectious disease: connecting innate immunity to biocidal polymers. / Mater. Sci. Eng. Rep. 2007, 57:28鈥?4. CrossRef
  7. Kenawy E-R, Worley SD, Broughton R: The chemistry and applications of antimicrobial polymers: A state-of-the-art review. / Biomacromolecules 2007, 8:1359鈥?384. CrossRef
  8. Klibanov AM: Permanently microbicidal materials coatings. / J Mater Chem 2007, 17:2479鈥?482. CrossRef
  9. Park D, Wang J, Klibanov AM: One-step, painting-like coating procedures to make surfaces highly and permanently bactericidal. / Biotechnol. Progr. 2006, 22:584鈥?89. CrossRef
  10. Tiller JC, Liao C-J, Lewis K, Klibanov AM: Designing surfaces that kill bacteria on contact. / P. Natl. Acad. Sci. USA 2001, 98:5981鈥?985. CrossRef
  11. Kenawy E-R, Abdel-Hay FI, El-Shanshoury A-ER, El-Newehy MH: Biologically Active polymers V: synthesis and antimicrobial activity of modified poly(glycidyl methacrylate-co-2-hydroxyethyl methacrylate) derivatives with quaternary ammonium and phosphonium salts. / J. Polym. Chem. Pol. Chem 2002, 40:2384鈥?393. CrossRef
  12. Chen CZ, Cooper SL: Interactions between dendrimer biocides and bacterial membranes. / Biomaterials 2002, 23:3359鈥?368. CrossRef
  13. Gottenbos B, Van der Mei HC, Klatter F, Nieuwenhuis P, Busscher HJ: In vitro and in vivo antimicrobial activity of covalently coupled quaternary ammonium silane coatings on silicone rubber. / Biomaterials 2002, 23:1417鈥?423. CrossRef
  14. Akashi A, Matsuya Y, Unemori M, Akamine A: Release profile of antimicrobial agents from 伪-tricalcium phosphate cement. / Biomaterials 2001, 22:2713鈥?717. CrossRef
  15. Munoz-Bonilla A, Fernandez-Garcia M: Polymeric materials with antimicrobial activity. / Prog Polym Sci 2012, 37:281鈥?39. CrossRef
  16. Park ES, Moon WS, Song MJ, Kim MN, Chung KH, Yoon JS: Antimicrobial activity of phenol and benzoic acid derivatives. / Int Biodeter Biodegr 2001, 47:209鈥?14. CrossRef
  17. Subramanyam E, Mohandoss S, Shin HW: Synthesis, characterization, and evaluation of antifouling polymers of 4-acryloyloxybenzaldehyde with methyl methacrylate. / J Appl Polym Sci 2009, 112:2741鈥?749. CrossRef
  18. Kenawy E-R, Abdel-Hay FI, El-Shanshoury A-ER, El-Newehy MH: Biologically active polymers: synthesis and antimicrobial activity of modified glycidyl methacrylate polymers having a quaternary ammonium and phosphonium groups. / J. Controll. Rel. 1998, 50:145鈥?52. CrossRef
  19. Akelah A, Moet A: / Functionalized polymers and their applications. London: Chapman and Hall; 1990.
  20. Chiu HT, Lin JM, Cheng TH, Chou SY: Fabrication of electrospun polyacrylonitrile ion-exchange membranes for application in lysozym. / eXPRESS Polym. Lett. 2011,5(4):308鈥?17. CrossRef
  21. Wang Z-G, Wan L-S, Xu Z-K: Surface engineerings of polyacrylonitrile-based asymmetric membranes towards biomedical applications: An overview. / J. Membrane Sci. 2007, 304:8鈥?3. CrossRef
  22. Shunkevich AA, Akulich Z I, Mediak GV, Soldatov VS: Acid鈥揵ase properties of ion exchangers. III. Anion exchangers on the basis of polyacrylonitrile fiber. / React Funct Polym 2005, 63:27鈥?4. CrossRef
  23. Dai Z-W, Nie F-Q, Xu Z-K: Acrylonitrile-based copolymer membranes containing reactive groups: Fabrication dual-layer biomimetic membranes by the immobilization of biomacromolecules. / J. Membrane Sci. 2005, 264:20鈥?6. CrossRef
  24. Yang M-C, Lin W-C: Surface modification and blood compatibility of polyacrylonitrile membrane with immobilized chitosan-heparin conjugate. / J. Polym. Res. 2002, 9:201鈥?06. CrossRef
  25. Braun D, Cherdron H, Rehahn M, Ritter H, Voit B: / Polymer synthesis: theory and practice. New York: Springer Berlin Heidelberg; 2005.
  26. El-Newehy MH, Alamri A, Al-Deyab SS: Optimization of amine-terminated polyacrylonitrile: synthesis and characterization. / Chem: Arab. J 2012. http://dx.doi.org/10.1016/j.arabjc.2012.04.041
  27. Kenawy ER, Abdel-Hay FI, Abou El-Magd A, Mahmoud Y: Biologically active polymers. VIII modification and antimicrobial activity of chitosan derivatives. / J. Bioact. Compat. Pol 2005, 20:95鈥?11. CrossRef
  28. Pridham T, Lindenfelser L, Shotwell O, Stodola F, Benedict R, Foley C, Jacks P, Zaumeyer W, Perston W, Mitchell J: Antibiotics against plant diseases: A laboratory and green house survey. / Phytopathology 1956, 46:568鈥?5.
  29. Shadomy S, Epsinel I, Cartwright R: Laboratory studies agents: Susceptibility test and bioassays. In / of: Manual of Clinical Microbiology. 4th edition. Edited by: Lennette A, Balows W, Hausler H, Shadomy S. Boston: Little Brown Co; 1985.
  30. Ardenne M, Beischer D: Untersuchung von metalloxyd-rauchen mit dem universal-elekronenmikroskop. / In: Zeitschrift elektrochemie 1940, 46:270鈥?77.
  31. Richards Cavill R: Electron microscope study of effect of benzalkonium chloride and edentate disodium on cell envelope of Pseudomonas aeruginosa. / Int. J. Pharm. Sci 1976, 65:76鈥?0. CrossRef
  32. Bradford M: A rapid and sensitive method for the quantitative of microgram quantities of protein utilizing principle of protein-dye binding. / Anal Biochem 1976, 72:248鈥?2. CrossRef
  33. Kissinger P: / Laboratory techniques in electroanalytical chemistry. United States: Harcourt Brace College Publishers; 1996.
  
• 作者单位：Abdullah Alamri (1)
  Mohamed H El-Newehy (1) (2)
  Salem S Al-Deyab (1)
  
  1. Petrochemical Research Chair, Department of Chemistry, College of Science, King Saud University, P.O. Box: 2455, Riyadh, 11451, Saudi Arabia
  2. Department of Chemistry, Faculty of Science, Tanta University, Tanta, 31527, Egypt
  
• ISSN：1752-153X

文摘

Background The design and applications of antimicrobial polymers is a growing field. Antimicrobial polymers can help to solve the problems associated with the use of conventional antimicrobial agents. Polymers with active functional groups can act as a carrier system for antimicrobial agents. In our study, we aim to prepare and develop some antimicrobial polymers for biomedical applications and water treatment. Results The antimicrobial polymers based on polyacrylonitrile (PAN) were prepared. Functional groups were created onto polyacrylonitrile via amination using different types of diamines such as ethylenediamine (EDA) and hexamethylenediamine (HMDA) to yield amine-terminated polymers. Antimicrobial polymers were obtained by immobilization of benzaldehyde and its derivatives which include, 4-hydroxybenzaldehyde and 2,4-dihydroxybenzaldehyde onto amine-terminated polymers. The antimicrobial activity of the prepared polymers against different types of microorganisms including Gram-positive bacteria (Staphylococcus aureus), Gram-negative bacteria (Pseudomonas aeruginosa; Escherichia coli; and Salmonella typhi) as well as fungi (Aspergillus flavus, Aspergillus niger, Candida albicans, Cryptpcoccus neoformans) were explored by the cut plug method and viable cell counting methods. Conclusions Amine-terminated polyacrylonitrile were used as a novel polymeric carrier for benzaldehyde derivatives as antimicrobial agents. The prepared polymers can inhibit the growth of the microorganisms. The activity was varied according to the tested microorganism as well as the polymer microstructure. It was found that the activity increased with increasing the number phenolic hydroxyl group of the bioactive group. Finally, it is anticipated that the prepared antimicrobial polymers would be of great help in the field of biomedical applications and biological water treatment.