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Erschienen in: Cellulose 10/2020

11.05.2020 | Original Research

Cyclodextrin and cellulose combination product developed by click chemistry: fascinating design for inclusion of ciprofloxacin

verfasst von: Lijian Sun, Shuaishuai Yang, Xueren Qian, Xianhui An

Erschienen in: Cellulose | Ausgabe 10/2020

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Abstract

In the current study, we introduce “click chemistry” as a powerful tool to tailor cyclodextrin–cellulose combination product followed by the inclusion of ciprofloxacin hydrochloride (CipHCl) as antibacterial agent. Initially, beta-cyclodextrin (β-CD) and cellulose fibers (CFs) were modified so as to be mono-6-propargylamino-6-deoxy-β-CD (Pro-β-CD) and azidated cellulose fibers (CFs-N3), respectively. Afterward, the “click reaction” was carried out between Pro-β-CD and CFs-N3 to fabricate a covalent grafting of β-CD onto CFs resulting in click product (CFs-N3@Pro-β-CD). The drug-delivery kinetics of the loaded CipHCl was performed by immersing samples into an aqueous solution, and the amount of adsorbed and released CipHCl was measured, as a function of time, by UV spectroscopy. Compared to original CFs, the load quantity of CipHCl into the click product was greatly increased, the release time of CipHCl from CFs-N3@Pro-β-CD was prolonged, and considerably higher antibacterial activity against E. coli and S. aureus was observed. The click product exhibited excellent antibacterial activity and sustained antibacterial efficacy up to 12 and 10 days against S. aureus and E. coli. The results showed that β-CD has been successfully grafted onto CFs via covalent bonds, while maintaining the intrinsic properties and the integrity of the fibers. Compared with the control paper sheet, the mechanical properties of the paper are well preserved.

Graphic abstract

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Literatur
Zurück zum Zitat Abd Rahman NS, Ahmad NA, Yhaya MF, Azahari B, Ismail WR (2016) Crosslinking of fibers via azide–alkyne click chemistry: synthesis and characterization. J Appl Polym Sci 133:43576 Abd Rahman NS, Ahmad NA, Yhaya MF, Azahari B, Ismail WR (2016) Crosslinking of fibers via azide–alkyne click chemistry: synthesis and characterization. J Appl Polym Sci 133:43576
Zurück zum Zitat Abdel-Halim ES, Al-Deyab SS, Alfaifi AY (2014) Cotton fabric finished with beta-cyclodextrin: inclusion ability toward antimicrobial agent. Carbohydr Polym 102:550–556PubMed Abdel-Halim ES, Al-Deyab SS, Alfaifi AY (2014) Cotton fabric finished with beta-cyclodextrin: inclusion ability toward antimicrobial agent. Carbohydr Polym 102:550–556PubMed
Zurück zum Zitat Ares AM, Muiño R, Costoya A, Lorenzo RA, Concheiro A, Carro AM, Alvarez-Lorenzo C (2019) Cyclodextrin-functionalized cellulose filter paper for selective capture of diclofenac. Carbohydr Polym 220:43–52PubMed Ares AM, Muiño R, Costoya A, Lorenzo RA, Concheiro A, Carro AM, Alvarez-Lorenzo C (2019) Cyclodextrin-functionalized cellulose filter paper for selective capture of diclofenac. Carbohydr Polym 220:43–52PubMed
Zurück zum Zitat Cai T, Neoh KG, Kang ET (2011) Poly(vinylidene fluoride) graft copolymer membranes with “clickable” surfaces and their functionalization. Macromolecules 44(11):4258–4268 Cai T, Neoh KG, Kang ET (2011) Poly(vinylidene fluoride) graft copolymer membranes with “clickable” surfaces and their functionalization. Macromolecules 44(11):4258–4268
Zurück zum Zitat Cai Q, Yang S, Zhang C, Li Z, Li X, Shen Z, Zhu W (2018) Facile and versatile modification of cotton fibers for persistent antibacterial activity and enhanced hygroscopicity. ACS Appl Mater Interfaces 10(44):38506–38516PubMed Cai Q, Yang S, Zhang C, Li Z, Li X, Shen Z, Zhu W (2018) Facile and versatile modification of cotton fibers for persistent antibacterial activity and enhanced hygroscopicity. ACS Appl Mater Interfaces 10(44):38506–38516PubMed
Zurück zum Zitat Carpenter BL, Scholle F, Sadeghifar H, Francis AJ, Boltersdorf J, Weare WW, Argyropoulos DS, Maggard PA, Ghiladi RA (2015) Synthesis, characterization, and antimicrobial efficacy of photomicrobicidal cellulose paper. Biomacromolecules 16(8):2482–2492PubMed Carpenter BL, Scholle F, Sadeghifar H, Francis AJ, Boltersdorf J, Weare WW, Argyropoulos DS, Maggard PA, Ghiladi RA (2015) Synthesis, characterization, and antimicrobial efficacy of photomicrobicidal cellulose paper. Biomacromolecules 16(8):2482–2492PubMed
Zurück zum Zitat Castro DO, Tabary N, Martel B, Gandini A, Belgacem N, Bras J (2016) Effect of different carboxylic acids in cyclodextrin functionalization of cellulose nanocrystals for prolonged release of carvacrol. Mater Sci Eng C 69:1018–1025 Castro DO, Tabary N, Martel B, Gandini A, Belgacem N, Bras J (2016) Effect of different carboxylic acids in cyclodextrin functionalization of cellulose nanocrystals for prolonged release of carvacrol. Mater Sci Eng C 69:1018–1025
Zurück zum Zitat Celebioglu A, Demirci S, Uyar T (2014) Cyclodextrin-grafted electrospun cellulose acetate nanofibers via “click” reaction for removal of phenanthrene. Appl Surf Sci 305:581–588 Celebioglu A, Demirci S, Uyar T (2014) Cyclodextrin-grafted electrospun cellulose acetate nanofibers via “click” reaction for removal of phenanthrene. Appl Surf Sci 305:581–588
Zurück zum Zitat Chang C, Zhang L, Zhou J, Zhang L, Kennedy JF (2010) Structure and properties of hydrogels prepared from cellulose in NaOH/urea aqueous solutions. Carbohydr Polym 82(1):122–127 Chang C, Zhang L, Zhou J, Zhang L, Kennedy JF (2010) Structure and properties of hydrogels prepared from cellulose in NaOH/urea aqueous solutions. Carbohydr Polym 82(1):122–127
Zurück zum Zitat Cova TF, Murtinho D, Pais A, Valente AJM (2018) Combining cellulose and cyclodextrins: fascinating designs for materials and pharmaceutics. Front Chem 6:271PubMedPubMedCentral Cova TF, Murtinho D, Pais A, Valente AJM (2018) Combining cellulose and cyclodextrins: fascinating designs for materials and pharmaceutics. Front Chem 6:271PubMedPubMedCentral
Zurück zum Zitat Crini G (2014) Review: a history of cyclodextrins. Chem Rev 114(21):10940–10975PubMed Crini G (2014) Review: a history of cyclodextrins. Chem Rev 114(21):10940–10975PubMed
Zurück zum Zitat Cusola O, Tabary N, Belgacem MN, Bras J (2013) Cyclodextrin functionalization of several cellulosic substrates for prolonged release of antibacterial agents. J Appl Polym Sci 129(2):604–613 Cusola O, Tabary N, Belgacem MN, Bras J (2013) Cyclodextrin functionalization of several cellulosic substrates for prolonged release of antibacterial agents. J Appl Polym Sci 129(2):604–613
Zurück zum Zitat de Castro DO, Tabary N, Martel B, Gandini A, Belgacem N, Bras J (2018) Controlled release of carvacrol and curcumin: bio-based food packaging by synergism action of TEMPO-oxidized cellulose nanocrystals and cyclodextrin. Cellulose 25(2):1249–1263 de Castro DO, Tabary N, Martel B, Gandini A, Belgacem N, Bras J (2018) Controlled release of carvacrol and curcumin: bio-based food packaging by synergism action of TEMPO-oxidized cellulose nanocrystals and cyclodextrin. Cellulose 25(2):1249–1263
Zurück zum Zitat Del Valle EMM (2004) Cyclodextrins and their uses: a review. Process Biochem 39(9):1033–1046 Del Valle EMM (2004) Cyclodextrins and their uses: a review. Process Biochem 39(9):1033–1046
Zurück zum Zitat Ding C, Sun L, Xiao G, Qian X, An X (2017) Green and combinational method towards clickable alkynylated cellulose fibers (ACFs). Cellulose 24(8):3219–3229 Ding C, Sun L, Xiao G, Qian X, An X (2017) Green and combinational method towards clickable alkynylated cellulose fibers (ACFs). Cellulose 24(8):3219–3229
Zurück zum Zitat Dong C, Qian L-Y, Zhao G-L, He B-H, Xiao H-N (2014a) Preparation of antimicrobial cellulose fibers by grafting β-cyclodextrin and inclusion with antibiotics. Mater Lett 124:181–183 Dong C, Qian L-Y, Zhao G-L, He B-H, Xiao H-N (2014a) Preparation of antimicrobial cellulose fibers by grafting β-cyclodextrin and inclusion with antibiotics. Mater Lett 124:181–183
Zurück zum Zitat Dong C, Ye Y, Qian L, Zhao G, He B, Xiao H (2014b) Antibacterial modification of cellulose fibers by grafting β-cyclodextrin and inclusion with ciprofloxacin. Cellulose 21(3):1921–1932 Dong C, Ye Y, Qian L, Zhao G, He B, Xiao H (2014b) Antibacterial modification of cellulose fibers by grafting β-cyclodextrin and inclusion with ciprofloxacin. Cellulose 21(3):1921–1932
Zurück zum Zitat Elchinger P-H, Montplaisir D, Zerrouki R (2012) Starch–cellulose crosslinking—towards a new material. Carbohydr Polym 87(2):1886–1890 Elchinger P-H, Montplaisir D, Zerrouki R (2012) Starch–cellulose crosslinking—towards a new material. Carbohydr Polym 87(2):1886–1890
Zurück zum Zitat Elchinger P-H, Awada H, Zerrouki C, Montplaisir D, Zerrouki R (2014) Kraft pulp–starch covalent linking: A promising route to a new material. Ind Eng Chem Res 53(18):7604–7610 Elchinger P-H, Awada H, Zerrouki C, Montplaisir D, Zerrouki R (2014) Kraft pulp–starch covalent linking: A promising route to a new material. Ind Eng Chem Res 53(18):7604–7610
Zurück zum Zitat Fallah Z, Nasr Isfahani H, Tajbakhsh M, Tashakkorian H, Amouei A (2017) TiO2-grafted cellulose via click reaction: an efficient heavy metal ions bioadsorbent from aqueous solutions. Cellulose 25(1):639–660 Fallah Z, Nasr Isfahani H, Tajbakhsh M, Tashakkorian H, Amouei A (2017) TiO2-grafted cellulose via click reaction: an efficient heavy metal ions bioadsorbent from aqueous solutions. Cellulose 25(1):639–660
Zurück zum Zitat Fatona A, Berry RM, Brook MA, Moran-Mirabal JM (2018) Versatile surface modification of cellulose fibers and cellulose nanocrystals through modular triazinyl chemistry. Chem Mater 30(7):2424–2435 Fatona A, Berry RM, Brook MA, Moran-Mirabal JM (2018) Versatile surface modification of cellulose fibers and cellulose nanocrystals through modular triazinyl chemistry. Chem Mater 30(7):2424–2435
Zurück zum Zitat Gopakumar DA, Pai AR, Pottathara YB, Pasquini D, Carlos de Morais L, Luke M, Kalarikkal N, Grohens Y, Thomas S (2018) Cellulose nanofiber-based polyaniline flexible papers as sustainable microwave absorbers in the x-band. ACS Appl Mater Interfaces 10(23):20032–20043PubMed Gopakumar DA, Pai AR, Pottathara YB, Pasquini D, Carlos de Morais L, Luke M, Kalarikkal N, Grohens Y, Thomas S (2018) Cellulose nanofiber-based polyaniline flexible papers as sustainable microwave absorbers in the x-band. ACS Appl Mater Interfaces 10(23):20032–20043PubMed
Zurück zum Zitat Guan Y, Xiao H, Sullivan H, Zheng A (2007) Antimicrobial-modified sulfite pulps prepared by in situ copolymerization. Carbohydr Polym 69(4):688–696 Guan Y, Xiao H, Sullivan H, Zheng A (2007) Antimicrobial-modified sulfite pulps prepared by in situ copolymerization. Carbohydr Polym 69(4):688–696
Zurück zum Zitat Guo Z, Jin Y, Liang T, Liu Y, Xu Q, Liang X, Lei A (2009) Synthesis, chromatographic evaluation and hydrophilic interaction/reversed-phase mixed-mode behavior of a "click beta-cyclodextrin" stationary phase. J Chromatogr A 1216(2):257–263PubMed Guo Z, Jin Y, Liang T, Liu Y, Xu Q, Liang X, Lei A (2009) Synthesis, chromatographic evaluation and hydrophilic interaction/reversed-phase mixed-mode behavior of a "click beta-cyclodextrin" stationary phase. J Chromatogr A 1216(2):257–263PubMed
Zurück zum Zitat Guo J, Filpponen I, Johansson L-S, Heiβler S, Li L, Levkin P, Rojas OJ (2017) Micro-patterns on nanocellulose films and paper by photo-induced thiol–yne click coupling: a facile method toward wetting with spatial resolution. Cellulose 25(1):367–375 Guo J, Filpponen I, Johansson L-S, Heiβler S, Li L, Levkin P, Rojas OJ (2017) Micro-patterns on nanocellulose films and paper by photo-induced thiol–yne click coupling: a facile method toward wetting with spatial resolution. Cellulose 25(1):367–375
Zurück zum Zitat Han Y, Zhang X, Wu X, Lu C (2015) Flame retardant, heat insulating cellulose aerogels from waste cotton fabrics by in situ formation of magnesium hydroxide nanoparticles in cellulose gel nanostructures. ACS Sustain Chem Eng 3(8):1853–1859 Han Y, Zhang X, Wu X, Lu C (2015) Flame retardant, heat insulating cellulose aerogels from waste cotton fabrics by in situ formation of magnesium hydroxide nanoparticles in cellulose gel nanostructures. ACS Sustain Chem Eng 3(8):1853–1859
Zurück zum Zitat Hiriart-Ramírez E, Contreras-García A, Garcia-Fernandez MJ, Concheiro A, Alvarez-Lorenzo C, Bucio E (2012) Radiation grafting of glycidyl methacrylate onto cotton gauzes for functionalization with cyclodextrins and elution of antimicrobial agents. Cellulose 19(6):2165–2177 Hiriart-Ramírez E, Contreras-García A, Garcia-Fernandez MJ, Concheiro A, Alvarez-Lorenzo C, Bucio E (2012) Radiation grafting of glycidyl methacrylate onto cotton gauzes for functionalization with cyclodextrins and elution of antimicrobial agents. Cellulose 19(6):2165–2177
Zurück zum Zitat Huang X, Wang A, Xu X, Liu H, Shang S (2016) Enhancement of hydrophobic properties of cellulose fibers via grafting with polymeric epoxidized soybean oil. ACS Sustain Chem Eng 5(2):1619–1627 Huang X, Wang A, Xu X, Liu H, Shang S (2016) Enhancement of hydrophobic properties of cellulose fibers via grafting with polymeric epoxidized soybean oil. ACS Sustain Chem Eng 5(2):1619–1627
Zurück zum Zitat Jazkewitsch O, Mondrzyk A, Staffel R, Ritter H (2011) Cyclodextrin-modified polyesters from lactones and from bacteria: an approach to new drug carrier systems. Macromolecules 44(6):1365–1371 Jazkewitsch O, Mondrzyk A, Staffel R, Ritter H (2011) Cyclodextrin-modified polyesters from lactones and from bacteria: an approach to new drug carrier systems. Macromolecules 44(6):1365–1371
Zurück zum Zitat Kang Z-Z, Zhang B, Jiao Y-C, Xu Y-H, He Q-Z, Liang J (2012) High-efficacy antimicrobial cellulose grafted by a novel quaternarized N-halamine. Cellulose 20(2):885–893 Kang Z-Z, Zhang B, Jiao Y-C, Xu Y-H, He Q-Z, Liang J (2012) High-efficacy antimicrobial cellulose grafted by a novel quaternarized N-halamine. Cellulose 20(2):885–893
Zurück zum Zitat Kawano S, Kida T, Miyawaki K, Noguchi Y, Kato E, Nakano T, Akashi M (2014) Cyclodextrin polymers as highly effective adsorbents for removal and recovery of polychlorobiphenyl (PCB) contaminants in insulating oil. Environ Sci Technol 48(14):8094–8100PubMed Kawano S, Kida T, Miyawaki K, Noguchi Y, Kato E, Nakano T, Akashi M (2014) Cyclodextrin polymers as highly effective adsorbents for removal and recovery of polychlorobiphenyl (PCB) contaminants in insulating oil. Environ Sci Technol 48(14):8094–8100PubMed
Zurück zum Zitat Khan AM, Shah SS (2009) pH induced partitioning and interactions of ciprofloxacin hydrochloride with anionic surfactant sodium dodecyl sulfate using ultraviolet and Fourier transformed infrared spectroscopy study. J Dispers Sci Technol 30(9):1247–1254 Khan AM, Shah SS (2009) pH induced partitioning and interactions of ciprofloxacin hydrochloride with anionic surfactant sodium dodecyl sulfate using ultraviolet and Fourier transformed infrared spectroscopy study. J Dispers Sci Technol 30(9):1247–1254
Zurück zum Zitat Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem 40:2004–2021 Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem 40:2004–2021
Zurück zum Zitat Kontturi KS, Kontturi E, Laine J (2013) Specific water uptake of thin films from nanofibrillar cellulose. J Mater Chem A 1(43):13655 Kontturi KS, Kontturi E, Laine J (2013) Specific water uptake of thin films from nanofibrillar cellulose. J Mater Chem A 1(43):13655
Zurück zum Zitat Kontturi KS, Biegaj K, Mautner A, Woodward RT, Wilson BP, Johansson LS, Lee KY, Heng JYY, Bismarck A, Kontturi E (2017) Noncovalent surface modification of cellulose nanopapers by adsorption of polymers from aprotic solvents. Langmuir 33(23):5707–5712PubMed Kontturi KS, Biegaj K, Mautner A, Woodward RT, Wilson BP, Johansson LS, Lee KY, Heng JYY, Bismarck A, Kontturi E (2017) Noncovalent surface modification of cellulose nanopapers by adsorption of polymers from aprotic solvents. Langmuir 33(23):5707–5712PubMed
Zurück zum Zitat Krouit M, Bras J, Belgacem MN (2008) Cellulose surface grafting with polycaprolactone by heterogeneous click-chemistry. Eur Polym J 44(12):4074–4081 Krouit M, Bras J, Belgacem MN (2008) Cellulose surface grafting with polycaprolactone by heterogeneous click-chemistry. Eur Polym J 44(12):4074–4081
Zurück zum Zitat Lavoine N, Tabary N, Desloges I, Martel B, Bras J (2014) Controlled release of chlorhexidine digluconate using beta-cyclodextrin and microfibrillated cellulose. Colloid Surface B 121:196–205 Lavoine N, Tabary N, Desloges I, Martel B, Bras J (2014) Controlled release of chlorhexidine digluconate using beta-cyclodextrin and microfibrillated cellulose. Colloid Surface B 121:196–205
Zurück zum Zitat Lee MH, Yoon KJ, Ko S (2015) Grafting onto cotton fiber with acrylamidomethylated β-cyclodextrin and its application. J Appl Polym Sci 78(11):1986–1991 Lee MH, Yoon KJ, Ko S (2015) Grafting onto cotton fiber with acrylamidomethylated β-cyclodextrin and its application. J Appl Polym Sci 78(11):1986–1991
Zurück zum Zitat Li JF, Zhang JX, Wang ZG, Yao YJ, Han X, Zhao YL, Liu JP, Zhang SQ (2017a) Identification of a cyclodextrin inclusion complex of antimicrobial peptide CM4 and its antimicrobial activity. Food Chem 221:296–301PubMed Li JF, Zhang JX, Wang ZG, Yao YJ, Han X, Zhao YL, Liu JP, Zhang SQ (2017a) Identification of a cyclodextrin inclusion complex of antimicrobial peptide CM4 and its antimicrobial activity. Food Chem 221:296–301PubMed
Zurück zum Zitat Li X, Zhang K, Shi R, Ma X, Tan L, Ji Q, Xia Y (2017b) Enhanced flame-retardant properties of cellulose fibers by incorporation of acid-resistant magnesium-oxide microcapsules. Carbohydr Polym 176:246–256PubMed Li X, Zhang K, Shi R, Ma X, Tan L, Ji Q, Xia Y (2017b) Enhanced flame-retardant properties of cellulose fibers by incorporation of acid-resistant magnesium-oxide microcapsules. Carbohydr Polym 176:246–256PubMed
Zurück zum Zitat Li J, Kang L, Wang B, Chen K, Tian X, Ge Z, Zeng J, Xu J, Gao W (2018) Controlled release and long-term antibacterial activity of dialdehyde nanofibrillated cellulose/silver nanoparticle composites. ACS Sustain Chem Eng 7(1):1146–1158 Li J, Kang L, Wang B, Chen K, Tian X, Ge Z, Zeng J, Xu J, Gao W (2018) Controlled release and long-term antibacterial activity of dialdehyde nanofibrillated cellulose/silver nanoparticle composites. ACS Sustain Chem Eng 7(1):1146–1158
Zurück zum Zitat Li Z, Liu W, Guan F, Li G, Song Z, Yu D, Wang H, Liu H (2019) Using cellulose fibers to fabricate transparent paper by microfibrillation. Carbohydr Polym 214:26–33PubMed Li Z, Liu W, Guan F, Li G, Song Z, Yu D, Wang H, Liu H (2019) Using cellulose fibers to fabricate transparent paper by microfibrillation. Carbohydr Polym 214:26–33PubMed
Zurück zum Zitat Liu W, Sun F, Jiang L, Meredith JC, Deng Y (2019) Surface structure patterning for fabricating non-fluorinated superhydrophobic cellulosic membranes. ACS Appl Polym Mater 1(5):1220–1229 Liu W, Sun F, Jiang L, Meredith JC, Deng Y (2019) Surface structure patterning for fabricating non-fluorinated superhydrophobic cellulosic membranes. ACS Appl Polym Mater 1(5):1220–1229
Zurück zum Zitat Mangiante G, Alcouffe P, Burdin B, Gaborieau M, Zeno E, Petit-Conil M, Bernard J, Charlot A, Fleury E (2013) Green nondegrading approach to alkyne-functionalized cellulose fibers and biohybrids thereof: synthesis and mapping of the derivatization. Biomacromolecules 14(1):254–263PubMed Mangiante G, Alcouffe P, Burdin B, Gaborieau M, Zeno E, Petit-Conil M, Bernard J, Charlot A, Fleury E (2013) Green nondegrading approach to alkyne-functionalized cellulose fibers and biohybrids thereof: synthesis and mapping of the derivatization. Biomacromolecules 14(1):254–263PubMed
Zurück zum Zitat Mao H, Dong Y, Qian X, An X (2017) Enhancement of bonding strength of polypyrrole/cellulose fiber (PPy/CF) hybrid through lignosulfonate doping. Cellulose 24(5):2255–2263 Mao H, Dong Y, Qian X, An X (2017) Enhancement of bonding strength of polypyrrole/cellulose fiber (PPy/CF) hybrid through lignosulfonate doping. Cellulose 24(5):2255–2263
Zurück zum Zitat Maver T, Maver U, Mostegel F, Griesser T, Spirk S, Smrke DM, Stana-Kleinschek K (2014) Cellulose based thin films as a platform for drug release studies to mimick wound dressing materials. Cellulose 22(1):749–761 Maver T, Maver U, Mostegel F, Griesser T, Spirk S, Smrke DM, Stana-Kleinschek K (2014) Cellulose based thin films as a platform for drug release studies to mimick wound dressing materials. Cellulose 22(1):749–761
Zurück zum Zitat Medronho B, Andrade R, Vivod V, Ostlund A, Miguel MG, Lindman B, Voncina B, Valente AJ (2013) Cyclodextrin-grafted cellulose: physico-chemical characterization. Carbohydr Polym 93(1):324–330PubMed Medronho B, Andrade R, Vivod V, Ostlund A, Miguel MG, Lindman B, Voncina B, Valente AJ (2013) Cyclodextrin-grafted cellulose: physico-chemical characterization. Carbohydr Polym 93(1):324–330PubMed
Zurück zum Zitat Meng X, Edgar KJ (2016) “Click” reactions in polysaccharide modification. Prog Polym Sci 53:52–85 Meng X, Edgar KJ (2016) “Click” reactions in polysaccharide modification. Prog Polym Sci 53:52–85
Zurück zum Zitat Munteanu M, Choi S, Ritter H (2009) Cyclodextrin-click-cucurbit[6]uril: combi-receptor for supramolecular polymer systems in water. Macromolecules 42(12):3887–3891 Munteanu M, Choi S, Ritter H (2009) Cyclodextrin-click-cucurbit[6]uril: combi-receptor for supramolecular polymer systems in water. Macromolecules 42(12):3887–3891
Zurück zum Zitat Nafie G, Vitale G, Carbognani Ortega L, Nassar NN (2017) Nanopyroxene grafting with beta-cyclodextrin monomer for wastewater applications. ACS Appl Mater Interfaces 9(48):42393–42407PubMed Nafie G, Vitale G, Carbognani Ortega L, Nassar NN (2017) Nanopyroxene grafting with beta-cyclodextrin monomer for wastewater applications. ACS Appl Mater Interfaces 9(48):42393–42407PubMed
Zurück zum Zitat Nongbe MC, Bretel G, Ekou L, Ekou T, Robitzer M, Le Grognec E, Felpin F-X (2018) Cellulose paper azide as a molecular platform for versatile click ligations: application to the preparation of hydrophobic paper surface. Cellulose 25(2):1395–1411 Nongbe MC, Bretel G, Ekou L, Ekou T, Robitzer M, Le Grognec E, Felpin F-X (2018) Cellulose paper azide as a molecular platform for versatile click ligations: application to the preparation of hydrophobic paper surface. Cellulose 25(2):1395–1411
Zurück zum Zitat Pan Y, Xiao H, Cai P, Colpitts M (2016) Cellulose fibers modified with nano-sized antimicrobial polymer latex for pathogen deactivation. Carbohydr Polym 135:94–100PubMed Pan Y, Xiao H, Cai P, Colpitts M (2016) Cellulose fibers modified with nano-sized antimicrobial polymer latex for pathogen deactivation. Carbohydr Polym 135:94–100PubMed
Zurück zum Zitat Roy D, Knapp JS, Guthrie JT, Perrier S (2008) Antibacterial cellulose fiber via RAFT surface graft polymerization. Biomacromolecules 9(1):91–99PubMed Roy D, Knapp JS, Guthrie JT, Perrier S (2008) Antibacterial cellulose fiber via RAFT surface graft polymerization. Biomacromolecules 9(1):91–99PubMed
Zurück zum Zitat Sadeghifar H, Venditti R, Jur J, Gorga RE, Pawlak JJ (2016) Cellulose-lignin biodegradable and flexible UV protection film. ACS Sustain Chem Eng 5(1):625–631 Sadeghifar H, Venditti R, Jur J, Gorga RE, Pawlak JJ (2016) Cellulose-lignin biodegradable and flexible UV protection film. ACS Sustain Chem Eng 5(1):625–631
Zurück zum Zitat Saini S, Quinot D, Lavoine N, Belgacem MN, Bras J (2016) β-Cyclodextrin-grafted TEMPO-oxidized cellulose nanofibers for sustained release of essential oil. J Mater Sci 52(7):3849–3861 Saini S, Quinot D, Lavoine N, Belgacem MN, Bras J (2016) β-Cyclodextrin-grafted TEMPO-oxidized cellulose nanofibers for sustained release of essential oil. J Mater Sci 52(7):3849–3861
Zurück zum Zitat Selvam S, Rajiv Gandhi R, Suresh J, Gowri S, Ravikumar S, Sundrarajan M (2012) Antibacterial effect of novel synthesized sulfated beta-cyclodextrin crosslinked cotton fabric and its improved antibacterial activities with ZnO, TiO2 and Ag nanoparticles coating. Int J Pharm 434(1–2):366–374PubMed Selvam S, Rajiv Gandhi R, Suresh J, Gowri S, Ravikumar S, Sundrarajan M (2012) Antibacterial effect of novel synthesized sulfated beta-cyclodextrin crosslinked cotton fabric and its improved antibacterial activities with ZnO, TiO2 and Ag nanoparticles coating. Int J Pharm 434(1–2):366–374PubMed
Zurück zum Zitat Singh R, Ho D, Lim LY, Iyer KS, Smith NM (2016) Colloidal polymeric platform for facile click-assisted ligand functionalization and receptor targeting. ACS Omega 1(6):1114–1120PubMedPubMedCentral Singh R, Ho D, Lim LY, Iyer KS, Smith NM (2016) Colloidal polymeric platform for facile click-assisted ligand functionalization and receptor targeting. ACS Omega 1(6):1114–1120PubMedPubMedCentral
Zurück zum Zitat Sun L, Qian X, Ding C, An X (2018) Integration of graft copolymerization and ring-opening reaction: a mild and effective preparation strategy for ‘‘clickable’’ cellulose fibers. Carbohydr Polym 198:41–50PubMed Sun L, Qian X, Ding C, An X (2018) Integration of graft copolymerization and ring-opening reaction: a mild and effective preparation strategy for ‘‘clickable’’ cellulose fibers. Carbohydr Polym 198:41–50PubMed
Zurück zum Zitat Sun L, Xiao G, Qian X, An X (2019a) Alkyne functionalized cellulose fibers: A versatile "clickable" platform for antibacterial materials. Carbohydr Polym 207:68–78PubMed Sun L, Xiao G, Qian X, An X (2019a) Alkyne functionalized cellulose fibers: A versatile "clickable" platform for antibacterial materials. Carbohydr Polym 207:68–78PubMed
Zurück zum Zitat Sun L, Ding C, Qian X, An X (2019b) Effective and simple one-step strategy for preparation of “clickable” cellulose modules: support to build antibacterial materials. Cellulose 26(3):1961–1976 Sun L, Ding C, Qian X, An X (2019b) Effective and simple one-step strategy for preparation of “clickable” cellulose modules: support to build antibacterial materials. Cellulose 26(3):1961–1976
Zurück zum Zitat Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1754PubMed Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1754PubMed
Zurück zum Zitat Szente L, Szeman J (2013) Cyclodextrins in analytical chemistry: host–guest type molecular recognition. Anal Chem 85(17):8024–8030PubMed Szente L, Szeman J (2013) Cyclodextrins in analytical chemistry: host–guest type molecular recognition. Anal Chem 85(17):8024–8030PubMed
Zurück zum Zitat Tungala K, Adhikary P, Krishnamoorthi S (2013) Trimerization of beta-cyclodextrin through the click reaction. Carbohydr Polym 95(1):295–298PubMed Tungala K, Adhikary P, Krishnamoorthi S (2013) Trimerization of beta-cyclodextrin through the click reaction. Carbohydr Polym 95(1):295–298PubMed
Zurück zum Zitat Tyagi P, Mathew R, Opperman C, Jameel H, Gonzalez R, Lucia L, Hubbe M, Pal L (2019) High-strength antibacterial chitosan-cellulose nanocrystal composite tissue paper. Langmuir 35(1):104–112PubMed Tyagi P, Mathew R, Opperman C, Jameel H, Gonzalez R, Lucia L, Hubbe M, Pal L (2019) High-strength antibacterial chitosan-cellulose nanocrystal composite tissue paper. Langmuir 35(1):104–112PubMed
Zurück zum Zitat Wang J, Cai Z (2008) Incorporation of the antibacterial agent, miconazole nitrate into a cellulosic fabric grafted with β-cyclodextrin. Carbohydr Polym 72(4):695–700 Wang J, Cai Z (2008) Incorporation of the antibacterial agent, miconazole nitrate into a cellulosic fabric grafted with β-cyclodextrin. Carbohydr Polym 72(4):695–700
Zurück zum Zitat Wang C, Qian X, An X (2015) In situ green preparation and antibacterial activity of copper-based metal–organic frameworks/cellulose fibers (HKUST-1/CF) composite. Cellulose 22(6):3789–3797 Wang C, Qian X, An X (2015) In situ green preparation and antibacterial activity of copper-based metal–organic frameworks/cellulose fibers (HKUST-1/CF) composite. Cellulose 22(6):3789–3797
Zurück zum Zitat Wei D, Li Z, Wang H, Liu J, Xiao H, Zheng A, Guan Y (2017) Antimicrobial paper obtained by dip-coating with modified guanidine-based particle aqueous dispersion. Cellulose 24(9):3901–3910 Wei D, Li Z, Wang H, Liu J, Xiao H, Zheng A, Guan Y (2017) Antimicrobial paper obtained by dip-coating with modified guanidine-based particle aqueous dispersion. Cellulose 24(9):3901–3910
Zurück zum Zitat Wittmar ASM, Fu Q, Ulbricht M (2017) Photocatalytic and magnetic porous cellulose-based nanocomposite films prepared by a green method. ACS Sustain Chem Eng 5(11):9858–9868 Wittmar ASM, Fu Q, Ulbricht M (2017) Photocatalytic and magnetic porous cellulose-based nanocomposite films prepared by a green method. ACS Sustain Chem Eng 5(11):9858–9868
Zurück zum Zitat Xiang Z, Chen Y, Liu Q, Lu F (2018) A highly recyclable dip-catalyst produced from palladium nanoparticle-embedded bacterial cellulose and plant fibers. Green Chem 20(5):1085–1094 Xiang Z, Chen Y, Liu Q, Lu F (2018) A highly recyclable dip-catalyst produced from palladium nanoparticle-embedded bacterial cellulose and plant fibers. Green Chem 20(5):1085–1094
Zurück zum Zitat Xiao G, Ding C, Song F, Qian X, An X (2016) Facile strategy for preparation of alkyne-functionalized cellulose fibers with click reactivity. Cellulose 24(2):591–607 Xiao G, Ding C, Song F, Qian X, An X (2016) Facile strategy for preparation of alkyne-functionalized cellulose fibers with click reactivity. Cellulose 24(2):591–607
Zurück zum Zitat Xu WZ, Gao G, Kadla JF (2013) Synthesis of antibacterial cellulose materials using a “clickable” quaternary ammonium compound. Cellulose 20(3):1187–1199 Xu WZ, Gao G, Kadla JF (2013) Synthesis of antibacterial cellulose materials using a “clickable” quaternary ammonium compound. Cellulose 20(3):1187–1199
Zurück zum Zitat Yan C, Liang N, Li Q, Yan P, Sun S (2019) Biotin and arginine modified hydroxypropyl-beta-cyclodextrin nanoparticles as novel drug delivery systems for paclitaxel. Carbohydr Polym 216:129–139PubMed Yan C, Liang N, Li Q, Yan P, Sun S (2019) Biotin and arginine modified hydroxypropyl-beta-cyclodextrin nanoparticles as novel drug delivery systems for paclitaxel. Carbohydr Polym 216:129–139PubMed
Zurück zum Zitat Yang H, van de Ven TG (2016) A bottom-uproute to a chemically end-to-end assembly of nanocellulose fibers. Biomacromolecules 17(6):2240–2247PubMed Yang H, van de Ven TG (2016) A bottom-uproute to a chemically end-to-end assembly of nanocellulose fibers. Biomacromolecules 17(6):2240–2247PubMed
Zurück zum Zitat Ye J, Liu H, Xiong J (2019) Preparation and properties of fluorescentcellulosic paper via surface coating of anionic cellulose ethers/rare earth metal ions composites. Ind Eng Chem Res 58(6):2370–2378 Ye J, Liu H, Xiong J (2019) Preparation and properties of fluorescentcellulosic paper via surface coating of anionic cellulose ethers/rare earth metal ions composites. Ind Eng Chem Res 58(6):2370–2378
Zurück zum Zitat Yu X, Tong S, Ge M, Wu L, Zuo J, Cao C, Song W (2013) Synthesis and characterization of multi-amino-functionalized cellulose for arsenic adsorption. Carbohydr Polym 92(1):380–387PubMed Yu X, Tong S, Ge M, Wu L, Zuo J, Cao C, Song W (2013) Synthesis and characterization of multi-amino-functionalized cellulose for arsenic adsorption. Carbohydr Polym 92(1):380–387PubMed
Zurück zum Zitat Zhang K, Zong L, Tan Y, Ji Q, Yun W, Shi R, Xia Y (2016) Improve the flame retardancy of cellulose fibers by grafting zinc ion. Carbohydr Polym 136:121–127PubMed Zhang K, Zong L, Tan Y, Ji Q, Yun W, Shi R, Xia Y (2016) Improve the flame retardancy of cellulose fibers by grafting zinc ion. Carbohydr Polym 136:121–127PubMed
Zurück zum Zitat Zhao D, Zhang Q, Chen W, Yi X, Liu S, Wang Q, Liu Y, Li J, Li X, Yu H (2017) Highly flexible and conductive cellulose-mediated PEDOT:PSS/MWCNT composite films for supercapacitor electrodes. ACS Appl Mater Interfaces 9(15):13213–13222PubMed Zhao D, Zhang Q, Chen W, Yi X, Liu S, Wang Q, Liu Y, Li J, Li X, Yu H (2017) Highly flexible and conductive cellulose-mediated PEDOT:PSS/MWCNT composite films for supercapacitor electrodes. ACS Appl Mater Interfaces 9(15):13213–13222PubMed
Metadaten
Titel
Cyclodextrin and cellulose combination product developed by click chemistry: fascinating design for inclusion of ciprofloxacin
verfasst von
Lijian Sun
Shuaishuai Yang
Xueren Qian
Xianhui An
Publikationsdatum
11.05.2020
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 10/2020
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-020-03200-y

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