Supramolecular Composite Materials from Cellulose, Chitosan, and Cyclodextrin: Facile Preparation and Their Selective Inclusion Complex Formation with Endocrine Disruptors

Duri, Simon; Tran, Chieu D.

doi:10.1021/la3050016

Cited by 37 publications

(57 citation statements)

References 48 publications

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“…For reference, the spectrum of CEL powder was also taken (orange curve). It exhibits several distinct different bands at around 1350cm −1 , 1147 cm −1 and 800 cm −1 which can be tentatively, assigned to the O-H bending vibration, the C-O stretching (of the C-OH group) and the C-H stretching, respectively (Duri & Tran, 2013; Harkins et al, 2014; Mututuvari & Tran, 2014; Tran et al, 2013a; Tran et al, 2013b). …”

Section: Resultsmentioning

confidence: 96%

“…Raw sheep wool (untreated), obtained from a local farm, was cleaned by Soxhlet extraction with a 1:1 acetone/ethanol mixture for 48 hrs. [BMIm + Cl − ] was prepared from freshly distilled 1-methylimidazole and n- chlorobutane (both from Alfa Aesar, Ward Hill, MA) using method previously reported ( Duri & Tran, 2013; Haverhals et al, 2012). …”

Section: Methodsmentioning

confidence: 99%

“…We have demonstrated recently that a simple ionic liquid, butylmethylimmidazolium chloride ([BMIm + Cl − ]), can dissolve polysaccharides such as CEL and chitosan (CS), and by use of this [BMIm + Cl − ] as the sole solvent, we developed a simple, green and totally recyclable method to synthesize [CEL+CS] composites just by dissolution without using any chemical modifications or reactions (Duri & Tran, 2013; Harkins et al, 2014; Mututuvari & Tran, 2013; Mututuvari & Tran, 2014; Tran et al, 2013a; Tran et al, 2013b). The [CEL+CS] composite obtained was found to be not only biodegradable and biocompatible but also retain unique properties of its components.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, structure and antimicrobial property of green composites from cellulose, wool, hair and chicken feather

Tran

Prosenc

Franko

et al. 2016

Carbohydrate Polymers

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Novel composites between cellulose (CEL) and keratin (KER) from three different sources (wool, hair and chicken feather) were successfully synthesized in a simple one-step process in which butylmethylimidazolium chloride (BMIm+Cl−), an ionic liquid, was used as the sole solvent. The method is green and recyclable because [BMIm+Cl−] used was recovered for reuse. Spectroscopy (FTIR, XRD) and imaging (SEM) results confirm that CEL and KER remain chemically intact and homogeneously distributed in the composites. KER retains some of its secondary structure in the composites. Interestingly, the minor differences in the structure of KER in wool, hair and feather produced pronounced differences in the conformation of their corresponding composites with wool has the highest α-helix content and feather has the lowest content. These results correlate well with mechanical and antimicrobial properties of the composites. Specifically, adding CEL into KER substantially improves mechanical strength of [CEL+KER] composites made from all three different sources, wool, hair and chicken feathers (i.e., [CEL+wool], [CEL+hair] and [CEL+feather]. Since mechanical strength is due to CEL, and CEL has only random structure, [CEL+feather] has, expectedly, the strongest mechanical property because feather has the lowest content of α-helix. Conversely, [CEL+wool] composite has the weakest mechanical strength because wool has the highest α-helix content. All three composites exhibit antibacterial activity against methicillin resistant S. aureus (MRSA). The antibacterial property is due not to CEL but to the protein and strongly depends on the type of the keratin, namely, the bactericidal effect is strongest for feather and weakest for wool. These results together with our previous finding that [CEL+KER] composites can control release of drug such as ciprofloxacin clearly indicate that these composites can potentially be used as wound dressing

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Section: Resultsmentioning

confidence: 96%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, structure and antimicrobial property of green composites from cellulose, wool, hair and chicken feather

Tran

Prosenc

Franko

et al. 2016

Carbohydrate Polymers

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“…In addition, the peak derived from the -OH group around 4800 cm −1 of MT and the -OH group around 4900 cm −1 of α CD was broadened (Figure 5(d)). A broadened or shifted peak in the NIR measurement indicated that there were intermolecular interactions between the drug and functional group [17]. This suggested that there were intermolecular interactions between the -CH 2 group and -OH group of MT and the -OH group of α CD in FD (MT/ α CD).…”

Section: Resultsmentioning

confidence: 99%

Characterization of α-Glucosidase Inhibitor/Cyclodextrin Complex Prepared by Freeze-Drying

Inoue

Narumi

Mitsumori

et al. 2018

Journal of Pharmaceutics

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Miglitol (MT) is an α-glucosidase inhibitor with a postmeal blood glucose level lowering effect that is used to treat type 2 diabetes. In addition, α-cyclodextrin (αCD) has been reported to inhibit increases in postmeal blood glucose. The aim of this study was to prepare a freeze-dried product (FD) composed of MT and αCD or γCD (molar ratio of MT/αCD = 1/1, MT/γCD = 1/1) and to evaluate the physicochemical properties and biological activity of the FD. The PXRD profile of FD exhibited a halo pattern, and characteristic peaks derived from MT, αCD, and γCD were not observed. The TG-DTA results for FD indicated an increased weight loss temperature and the absence of an endothermic peak for MT. The NIR absorption spectrum measurement suggested an intermolecular interaction between MT and αCD or γCD in the FD. 1H-1H NOESY NMR spectroscopy (D2O) revealed an intermolecular interaction in the FD. The results of the α-glucosidase activity inhibition test and the α-amylase activity inhibition test indicated that the FD exhibited the same inhibition rate as MT alone and the effects of MT were not altered by the freeze-drying method.

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“…23–25 The [CEL+CS] composite obtained was found to be not only biodegradable and biocompatible but also retain unique properties of its component, namely superior mechanical strength (from CEL) and excellent antibacterial and adsorption capability for pollutants and toxins (from CS). 23–25 …”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Selective Adsorption of Amino Acid by Polysaccharide Composite Materials

Duri

Tran

2014

Langmuir

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A composite containing cellulose (CEL) and chitosan (CS) synthesized by a simple and recyclable method by using butylmethylimmidazolium chloride, an ionic liquid, was found to exhibit remarkable enantiomeric selectivity toward adsorption of amino acids. 100%CS shows the highest adsorption capacity and enantiomeric selectivity. A racemic amino acid can be enantiomerically resolved by 100%CS in about 96–120 hrs. Interestingly, adsorption by 50:50 CEL:CS is more similar to that by 100%CS than to 100%CEL. Specifically, while 100% CEL shows lowest adsorption capacity and enantiomeric selectivity, 50:50 CEL:CS has sufficient enantiomeric selectivity to enable it to be used for chiral resolution. This is very significant because in spite of its high enantiomeric selectivity, 100%CS cannot practically be used because it has relatively poor mechanical properties and undergoes extensive swelling. Adding 50% of CEL to CS substantially improves the mechanic properties and reduces its swelling while retains sufficient enantiomeric selectivity to enable it to be used for routine chiral separations. Kinetic results indicate that the enantiomeric selective adsorption is due not to the initial surface adsorption but rather to the subsequent stage in which the adsorbate molecules diffuse into the pores within the particle of the composites and consequently got adsorbed by the interior of each particle. The strong inter- and intramolecular hydrogen bond network in CEL enables it to adopt a very dense structure which makes it difficult for adsorbate molecules to diffuse to its interior thereby leading to low enantiomeric selectivity. Compared to hydroxy group, amino group cannot form strong hydrogen bond. The hydrogen bond network in CS is not as extensive as in CEL, and its inner structure is relatively less dense than CEL. Adsorbate molecules can, therefore, diffuse from the outer surface to its inner structure relatively easier than in CEL, thereby leading to higher enantiomeric selectivity for 100%CS.

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Supramolecular Composite Materials from Cellulose, Chitosan, and Cyclodextrin: Facile Preparation and Their Selective Inclusion Complex Formation with Endocrine Disruptors

Cited by 37 publications

References 48 publications

Synthesis, structure and antimicrobial property of green composites from cellulose, wool, hair and chicken feather

Synthesis, structure and antimicrobial property of green composites from cellulose, wool, hair and chicken feather

Characterization of α-Glucosidase Inhibitor/Cyclodextrin Complex Prepared by Freeze-Drying

Enantiomeric Selective Adsorption of Amino Acid by Polysaccharide Composite Materials

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