Top

Polymer Bulletin

Published in:

16-11-2018 | Original Paper

Aminophosphonic groups grafted onto the structure of macroporous styrene–divinylbenzene copolymer: preparation and studies on the antimicrobial effect

Authors: I. Nichita, L. Lupa, M. Stoia, E. S. Dragan, A. Popa

Published in: Polymer Bulletin | Issue 9/2019

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

This paper has investigated the preparation, characterization and antimicrobial effect of two new compounds. α-Aminophosphonic acid groups were grafted onto the structure of a styrene-6.7% divinylbenzene (S-6.7% DVB) copolymer. The compounds bearing the N–C–P skeleton in α-aminophosphonic acids groups were synthesized following a “one-pot” modified Kabachnik–Fields reaction performed with three components (polymeric amine, aldehyde and phosphorous acid) in tetrahydrofuran at 55 °C. The presence of 2 novel products: aminobenzylphosphonic acid (BzAmPhonic) and aminopropylphosphonic acid (PrAmPhonic) grafted on (S-6.7% DVB) copolymer was indicated by characterization using FT-IR spectroscopy, EDX, TGA, measurement of the phosphorus content and the degree of functionalization with pendant α-aminophosphonic acid group. It was proved that novel products have an antimicrobial effect in vitro after 1 h of contact against Staphylococcus aureus (S. aureus), Escherichia coli (E. coli), Bacillus cereus (B. cereus), Pseudomonas aeruginosa (P. aeruginosa) and a species of yeast Candida albicans (C. albicans). The best antibacterial activity was obtained by the PrAmPhonic sample. We were interested in obtaining new polymeric functionalized compounds endowed with very good antimicrobial properties. The main advantage of the novel antibacterial agents synthesized in this work is that they can be easily recovered in order not to contaminate the environment.

previous article One-pot and two-step method preparation of polyvinyl alcohol/phytic acid polymer sponge under microwave irradiation and physical property study

next article Synthesis, characterization, and self-assembly behavior of poly(m-phenylene)s with terthiophene and chiral side chains

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Keglevich G, Bálint E (2012) The Kabachnik–Fields reaction: mechanism and synthetic use. Molecules 17:12821–12835. https://doi.org/10.3390/molecules171112821 CrossRefPubMedPubMedCentral

Naydenova ED, Todorov PT, Troev KD (2010) Recent synthesis of aminophosphonic acids as potential biological importance. Amino Acids 38:23–30. https://doi.org/10.1007/s00726-009-0254-7 CrossRefPubMed

Kafarski P, Górniak MG, Andrasiak I (2015) Kabachnik–Fields reaction under green conditions—A critical over-view. Curr Green Chem 2:218–222CrossRef

Wang Q, Zhu M, Zhu R, Lu L, Yuan C, Xing S, Fu X, Mei Y, Hang Q (2012) Exploration of a-aminophosphonate N-derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatases. Eu J Med Chem 49:354–364. https://doi.org/10.1016/j.ejmech.2012.01.038 CrossRef

Naydenova E, Topashka-Ancheva M, Todorov P, Ts Yordanova, Troev K (2006) Novel a-aminophosphonic acids. Design, characterization, and biological activity. Bioorg Med Chem 14:2190–2196. https://doi.org/10.1016/j.bmc.2005.11.002 CrossRefPubMed

Todorov PT, Pavlov ND, Shivachev BL, Petrova RN, Martinez J, Naydenova ED, Calmes M (2012) Synthesis of new racemic and optically active N-phosphonoalkyl bicyclic β-AminoAcids via the Kabachnik–fields reaction as potential biologically active compound. Heteroatom Chem 23(2):123–130. https://doi.org/10.1002/hc.20759 CrossRef

Demkowicz S, Rachon J, Dasko M, Kozak W (2016) Selected organophosphorus compounds with biological activity. Applications in medicine. RSC Adv 6:7101–7112. https://doi.org/10.1039/C5RA25446A CrossRef

Villemin D, Didi MA (2015) Aminomethylenephosphonic acids syntheses and applications. Oriental J Chem 31:1–12. https://doi.org/10.13005/ojc/31.Special-Issue1.01 CrossRef

Guo Y-C, Li J, Ma J-L, Yu Z-R, Wang H-W, Zhu W-J, Liao X-C, Zhao Y-F (2015) Synthesis and antitumor activity of α-aminophosphonate derivatives containing thieno[2,3-d]pyrimidines. Chin Chem Lett 26(6):755–758. https://doi.org/10.1016/j.cclet.2015.03.026 CrossRef

10.

Popa A, Ilia G, Iliescu S, Dehelean G, Pascariu A, Bora A, Pacureanu L (2004) Mixed quaternary ammonium and phosphonium salts bound to macromolecular supports for removal bacteria from water. Mol Cryst Liq Cryst 418:195–203. https://doi.org/10.1080/15421400490479280 CrossRef

11.

Pendleton JN, Gilmore BF (2015) The antimicrobial potential of ionic liquids: a source of chemical diversity for infection and biofilm control. Int J Antimicrob Agents 46:131–139. https://doi.org/10.1016/j.ijantimicag.2015.02.016 CrossRefPubMed

12.

Alamri A, El-Newehy MH, Al-Deyab SS (2012) Biocidal polymers: synthesis and antimicrobial properties of benzaldehyde derivatives immobilized onto amine-terminated polyacrylonitrile. Chem Cent J 6(111):1–13. https://doi.org/10.1186/1752-153X-6-111 CrossRef

13.

Gao B, Liu Q, Li Y (2010) Preparation of water-insoluble antibacterial materials with surface-grafted material PSt/SIO₂ and their antibacterial activity. J Polym Environ 18(4):474–483. https://doi.org/10.1007/s10924-010-0187-y CrossRef

14.

Zhang Y, Zhang H, Liu Y, Zhang ZL, Ding CK (2018) Chelating ability and microbial stability of an l-arginine-modified chitosan-based environmental remediation material. J Polym Environ 26(3):885–894. https://doi.org/10.1007/s10924-017-1000-y CrossRef

15.

Palza H (2015) Antimicrobial polymers with metal nanoparticles. Int J Mol Sci 16(1):2099–2116. https://doi.org/10.3390/ijms16012099 CrossRefPubMedPubMedCentral

16.

Ganewatta MS, Tang C (2015) Controlling macromolecular structures towards effective antimicrobial polymers. Polymer 63:A1–A29. https://doi.org/10.1016/j.polymer.2015.03.007 CrossRef

17.

Huang K-S, Yang C-H, Huang S-L, Chen C-Y, Lu Y-Y, Lin Y-S (2016) Recent advances in antimicrobial polymers: a mini-review. Int J Mol Sci 17:1578. https://doi.org/10.3390/ijms17091578 CrossRefPubMedCentral

18.

Li C, Liu Y, Cao P, He J, Lin Z, Ao N, Chu B (2014) Quaternary phosphonium modified epoxidized natural rubber: effect of reaction time, reaction mechanism, thermal property and antimicrobial activity. Polym Bull 71(10):2543–2557. https://doi.org/10.1007/s00289-014-1206-2 CrossRef

19.

Popa A, Davidescu CM, Trif R, Ilia Gh, Iliescu S, Dehelean Gh (2003) Study of quaternary ‘onium’ salts grafted on polymers: antibacterial activity of quaternary phosphonium salts grafted on ‘gel-type’ styrene- divinylbenzene copolymers. React Funct Polym 55:151–158. https://doi.org/10.1016/S1381-5148(02)00224-9 CrossRef

20.

Xue Y, Xiao H, Zhang Y (2015) Antimicrobial Polymeric Materials with Quaternary Ammonium and Phosphonium Salts. Int J Mol Sci 16:3626–3655. https://doi.org/10.3390/ijms16023626 CrossRefPubMedPubMedCentral

21.

Nichita I, Popa A, Dragan ES, Iliescu S, Ilia G (2015) Grafted α-hydroxyphosphonic acids onto polymeric supports: preparation, characterization, and antimicrobial effect. J Biomat Sci-Polym E 26(8):483–496. https://doi.org/10.1080/09205063.2015.1030990 CrossRef

22.

Qian C, Huang T (1998) One-pot synthesis of α-amino phosphonates from aldehydes using lanthanide triflate as a catalyst. J Org Chem 63:4125–4128. https://doi.org/10.1021/jo971242t CrossRef

23.

Popa A, Parvulescu V, Plesu N, Iliescu S, Davidescu CM (2008) Synthesis of aminophosphonates grafted on styrene divinylbenzene copolymer. Mater Plast (Bucuresti) 45(4):310–313

24.

Alexandratos SD, Hong M-J (2002) Enhanced metal ion affinities by supported ligand synergistic interaction in bifunctional polymer-supported aminomethylphosphonates. Sep Sci Technol 37(11):2587–2605. https://doi.org/10.1081/SS-120004454 CrossRef

25.

Ciopec M, Davidescu CM, Negrea A, Lupa L, Popa A, Muntean C, Ardelean R, Ilia G (2013) Synthesis, characterization, and adsorption behavior of aminophosphinic grafted on poly(styrene-codivinylbenzene) for divalent metal ions in aqueous solutions. Polym Eng Sci 53(5):1117–1124. https://doi.org/10.1002/pen.23365 CrossRef

26.

Davidescu CM, Ciopec M, Negrea A, Popa A, Lupa L, Dragan ES, Ardelean R, Ilia G, Iliescu S (2013) Synthesis, characterization, and Ni(II) ion sorption properties of poly(styrene-co-divinylbenzene) functionalized with aminophosphonic acid groups. Polym Bull 70:277–291. https://doi.org/10.1007/s00289-012-0801-3 CrossRef

27.

Negrea A, Ciopec M, Negrea P, Lupa L, Popa A, Davidescu CM, Ilia G (2015) Separation of AsV from aqueous solutions using chelating polymers containing FeIII-loaded phosphorus groups. Open Chem 13:105–112. https://doi.org/10.1515/chem-2015-0025 CrossRef

28.

Davidescu CM, Popa A (2002) The synthesis of styrene-divinylbenzene copolymers with phosphonic groups by linkages of N-beta-amionethyl-aminomethyl type. Mater Plast (Bucuresti) 39(1):50–55

29.

Albert F, Barbulescu N, Holszky C, Grefts C (1970) Analiză chimică organică [Organic Chemistry Analysis]. Ed. Tehnică, Bucureşti, pp 83–85

30.

Popa A, Ilia G, Pascariu A, Iliescu S, Plesu N (2005) Grafted styrene-divinylbenzene copolymers containing benzaldehydes and their wittig reactions with various phosphonium salts. Chin J Polym Sci 23(6):651–656. https://doi.org/10.1142/S0256767905000862 CrossRef

31.

Popa A, Davidescu CM, Petru N, Gheorghe I, Katsaros A, Demadis KD (2008) Synthesis and characterization of phosphonate ester/phosphonic acid-grafted styrene–divinylbenzene copolymer microbeads and their utility in adsorption of divalent metal ions in aqueous solutions. Ind Eng Chem Res 47:2010–2017. https://doi.org/10.1021/ie070886g CrossRef

32.

Haul R, Dümbgen G (1960) Vereinfachte Methode zur Messung von Oberflächengrößen durch Gasadsorption. Chem Ing Tech 32:349–354CrossRef

33.

Raducanescu H, Bica-Popii V (1986) Bacteriologie veterinara [Veterinary Bacteriology]. Ceres, Bucuresti, pp 123–125

34.

Augusta S, Cruber HF, Streichsbier F (1994) Synthesis and antibacterial activity of immobilized quaternary ammonium salts. J Appl Polym Sci 53:1149–1163. https://doi.org/10.1002/app.1994.070530903 CrossRef

35.

Kawabata N, Ueno Y, Torii K, Matsumoto T (1987) Capturing Interaction between Insoluble Pyridinium-type Polymer and Bacterial Cells. Agric. Bioi Chem 51(4):1085–1090. https://doi.org/10.1080/00021369.1987.10868151 CrossRef

36.

Cox JS, Smith SD, Warren LA, Ferris GF (1999) Characterizing Heterogeneous Bacterial Surface Functional Groups Using Discrete Affinity Spectra for Proton Binding. Environ Sci Technol 33:4514–4521. https://doi.org/10.1021/es990627l CrossRef

37.

Jiang W, Saxena A, Song B, Ward BB, Beveridge T, Myneni SCB (2004) Elucidation of functional groups on gram-positive and gram-negative bacterial surfaces using infrared spectroscopy. Langmuir 20:11433–11442, https://www.princeton.edu/nitrogen/publications/pdfs/JiangWard_2004.pdf

38.

Beveridge TJ (1999) Structure of Gram-negative cell walls and their derived membrane vesicles. J Bacteriol 181:4725–4733PubMedPubMedCentral

39.

An YH, Friedman RJ (1998) Concise review of mechanisms of bacterial adhesion to biomaterial surfaces. Inc J Biomed Mater Res (Appl Biomater) 43:338–348. https://doi.org/10.1002/(SICI)1097-4636(199823)43:3%3c338:AID-JBM16%3e3.0.CO;2-B CrossRef

40.

Popa A, Davidescu C-M, Trif R, Ilia G, Iliescu S, Dehelean G (2003) Polycationic biocides with pendant quaternary groups. II. Synthesis and antimicrobial activity of ammonium salts grafted on gel-type styrene-divinylbenzene copolymers against Staphylococcus Aureus And Escherichia Coli. Rev Roum Chim 48(9):729–734

41.

Kanazawa A, Ikedo T, Endo T (1994) Polymeric Phosphonium salts as a novel class of cationic biocides. VIII. Synergic effect on antibacterian activity of polymeric phosphonium and ammonium salts. J Appl Polym Sci 53:1245–1249CrossRef

42.

Bowman SM, Free SJ (2006) The structure and synthesis of the fungal cell wall. BioEssays 28:799–808. https://doi.org/10.1002/bies.20441 CrossRefPubMed

43.

Cabib E, Bowers B, Sburlati A, Silverman SJ (1988) Fungal cell wall synthesis: the construction of a biological structure. Microbiol Sci 5:370–375PubMed

44.

Brown JA, Catley BJ (1992) Monitoring polysaccharide synthesis in Candida albicans. Carbohydr Res 227:195–202. https://doi.org/10.1016/0008-6215(92)85071-7 CrossRef

45.

Lee Y-S, Byoun Y-S (2002) Poly (styrene-co-4-vinylbenzyl chloride) conjugated with 3-(dimethylamino) phenol: synthesis and antibacterial activity. Bull Korean Chem Soc 23(12):1833–1835CrossRef

Title: Aminophosphonic groups grafted onto the structure of macroporous styrene–divinylbenzene copolymer: preparation and studies on the antimicrobial effect
Authors: I. Nichita
L. Lupa
M. Stoia
E. S. Dragan
A. Popa
Publication date: 16-11-2018
Publisher: Springer Berlin Heidelberg
Published in: Polymer Bulletin / Issue 9/2019
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-018-2613-6

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 9/2019

Preparation of Ag2Se QDs with excellent aqueous dispersion stability by organic coating with aqueous ATRP

Voltammetric and chronoamperometric studies of aniline electropolymerization in different aqueous sulfuric acid solutions

One-pot and two-step method preparation of polyvinyl alcohol/phytic acid polymer sponge under microwave irradiation and physical property study

Poly(hydroxyamide) as support for thin-film composite membranes for water treatment

Effect of the preparation method in the size of chitosan nanoparticles for the removal of allura red dye

Mucoadhesive nanofibrous membrane with anti-inflammatory activity

Premium Partners