Immobilized furanone derivatives as inhibitors for adhesion of bacteria on modified poly(styrene-co-maleic) anhydride)

N.P. Gule, O. Bshena, M. Kwaadsteniet, de, T.E. Cloete, L. Klumperman

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Abstract

The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water (Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia coli Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy (1H NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).
Original languageEnglish
Pages (from-to)3138-3150
JournalBiomacromolecules
Volume13
Issue number10
DOIs
Publication statusPublished - 2012

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Maleic anhydride
Styrene
Bacteria
Adhesion
Derivatives
Water
Nuclear magnetic resonance
Maleic Anhydrides
Spectroscopy
Salmonella
Cell adhesion
Nanofibers
Gas chromatography
Escherichia coli
Nuclear magnetic resonance spectroscopy
Fourier transform infrared spectroscopy
Scanning electron microscopy
poly(styrene-co-maleic anhydride)

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Gule, N.P. ; Bshena, O. ; Kwaadsteniet, de, M. ; Cloete, T.E. ; Klumperman, L. / Immobilized furanone derivatives as inhibitors for adhesion of bacteria on modified poly(styrene-co-maleic) anhydride). In: Biomacromolecules. 2012 ; Vol. 13, No. 10. pp. 3138-3150.
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abstract = "The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water (Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia coli Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy (1H NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).",
author = "N.P. Gule and O. Bshena and {Kwaadsteniet, de}, M. and T.E. Cloete and L. Klumperman",
year = "2012",
doi = "10.1021/bm300932u",
language = "English",
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pages = "3138--3150",
journal = "Biomacromolecules",
issn = "1525-7797",
publisher = "American Chemical Society",
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Gule, NP, Bshena, O, Kwaadsteniet, de, M, Cloete, TE & Klumperman, L 2012, 'Immobilized furanone derivatives as inhibitors for adhesion of bacteria on modified poly(styrene-co-maleic) anhydride)', Biomacromolecules, vol. 13, no. 10, pp. 3138-3150. https://doi.org/10.1021/bm300932u

Immobilized furanone derivatives as inhibitors for adhesion of bacteria on modified poly(styrene-co-maleic) anhydride). / Gule, N.P.; Bshena, O.; Kwaadsteniet, de, M.; Cloete, T.E.; Klumperman, L.

In: Biomacromolecules, Vol. 13, No. 10, 2012, p. 3138-3150.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Immobilized furanone derivatives as inhibitors for adhesion of bacteria on modified poly(styrene-co-maleic) anhydride)

AU - Gule, N.P.

AU - Bshena, O.

AU - Kwaadsteniet, de, M.

AU - Cloete, T.E.

AU - Klumperman, L.

PY - 2012

Y1 - 2012

N2 - The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water (Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia coli Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy (1H NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).

AB - The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water (Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia coli Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy (1H NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).

U2 - 10.1021/bm300932u

DO - 10.1021/bm300932u

M3 - Article

C2 - 22947312

VL - 13

SP - 3138

EP - 3150

JO - Biomacromolecules

JF - Biomacromolecules

SN - 1525-7797

IS - 10

ER -