β-Cyclodextrin-Functionalized Cellulose Nanocrystals and Their Interactions with Surfactants

Zhang, Feifei; Islam, Muhammad Shahidul; Berry, Richard M.; Tam, Kam Chiu

doi:10.1021/acsomega.8b02534

Cited by 16 publications

(9 citation statements)

References 35 publications

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“…10 mg of each of the BBE polymers was added to 25 mL of the phenolphthalein solution, stirred, and equilibrated overnight and the absorbance was measured and the βCD concentration in the polymers was determined by referring to the standard curve. PHTH does not bind to the BHNC pristine and the measured absorbance would hence only reflect PHTH in the βCD cavities 45 . The βCD content of the BBE polymers was determined using the following equation:…”

Section: Phenolphthalein (Phth) Assay For βCd Grafting Ratio Of Bbesmentioning

confidence: 99%

pH-responsive polymer-based biomacromolecule nanosponges as biodegradable carriers for DOX delivery

Nia

Ashkar

Munguia-Lopez

et al. 2021

Preprint

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Cellulose is the most abundant renewable biomaterial on earth and beta-cyclodextrin (BCD) is among the most commonly used biocompatible drug encapsulation agents. Combining these bio-organic materials is a very powerful approach to greatly enhance the bioavailability of many drugs. These systems also allow for optimal selective drug release profiles, high biocompatibility, as well as “green nanomedicine” approaches that are eco-friendly in their synthesis and have minimal ecological toxicity. herein, we designed a new type of green and biopolymer-based nanosponge drug carriers which is polymerized by crosslinking beta-cyclodextrin ethylene diamine (βCD-EDA) with bifunctional hairy nanocellulose (BHNC). BHNC contains, besides aldehyde groups, carboxyl groups which can react with amino groups in βCD-EDA. Firstly, the crosslinker βCD-EDA was obtained through a simple nucleophilic substitution reaction between beta-cyclodextrin carbonyl imidazole (βCD-CI) and ethylene diamine (EDA). Secondly, BHNC was functionalized with the crosslinker βCD-EDA through a facile nucleophilic substitution crosslinking reaction of the BHNC activated carboxyl groups by the amines of βCD-EDA. We refer to the polymerized highly crosslinked BHNC-βCD-EDA network as BBE. Various ratios of βCD-EDA and BHNC were polymerized with the help of DMTMM as an activator, which resulted in different morphological shapes of BBE, and thus in different release profiles and pH-responsiveness. Unlike other polymer-based βCDs and nanosponges, these new types of crosslinked polymer were prepared in a green and safe solvent (water) and with very short reaction times and at low temperatures. Finally, the BBE polymers were tested as biocompatible nanocarriers for controllable doxorubicin (DOX) delivery. These hyper crosslinked polymers show a high capacity for loading DOX with extended drug release. Furthermore, breast cancer cell cultures show lower cell viability when DOX was loaded in various BBEs than control samples or DOX alone, indicating that our DOX-BBE drug delivery systems are better anticancer agents than DOX alone.

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Section: Phenolphthalein (Phth) Assay For βCd Grafting Ratio Of Bbesmentioning

confidence: 99%

pH-responsive polymer-based biomacromolecule nanosponges as biodegradable carriers for DOX delivery

Nia

Ashkar

Munguia-Lopez

et al. 2021

Preprint

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“…Cyclodextrins are capable of forming complexes with a wide range of molecules, but they cannot form a direct covalent bond with textile materials; therefore, some cyclodextrin derivatives have been synthesized with reactive groups to allow them to chemically bond to various substrates [122], as shown in Figure 5. One of the most common reactive derivatives of cyclodextrins is MCT-β-CD, as seen in Figure 5a, synthesized through the reaction between cyanuric chloride and β-cyclodextrin [123]. MCT-β-CD is the most interesting derivative used on cellulosic substrates due to the simple bonding process in relatively mild conditions.…”

Section: Preparation Of Cyclodextrinsmentioning

confidence: 99%

“…The monochlorotriazine groups incorporated into the CDs react by a nucleophilic substitution mechanism, and form covalent bonds with the hydroxyl groups of the cellulose [124]. Another product that can be synthesized from MCT-β-CD is the cyclodextrin polymer One of the most common reactive derivatives of cyclodextrins is MCT-β-CD, as seen in Figure 5a, synthesized through the reaction between cyanuric chloride and β-cyclodextrin [123]. MCT-β-CD is the most interesting derivative used on cellulosic substrates due to the simple bonding process in relatively mild conditions.…”

Section: Preparation Of Cyclodextrinsmentioning

confidence: 99%

“…One of the most common reactive derivatives of cyclodextrins is MCT-β-CD, as seen in Figure 5 a, synthesized through the reaction between cyanuric chloride and β-cyclodextrin [ 123 ]. MCT-β-CD is the most interesting derivative used on cellulosic substrates due to the simple bonding process in relatively mild conditions.…”

Section: Application Of Cyclodextrins In the Textile Areamentioning

confidence: 99%

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The Role of β-Cyclodextrin in the Textile Industry—Review

Bezerra

Arias²,

Firmino

et al. 2020

Molecules

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β-Cyclodextrin (β-CD) is an oligosaccharide composed of seven units of D-(+)-glucopyranose joined by α-1,4 bonds, which is obtained from starch. Its singular trunk conical shape organization, with a well-defined cavity, provides an adequate environment for several types of molecules to be included. Complexation changes the properties of the guest molecules and can increase their stability and bioavailability, protecting against degradation, and reducing their volatility. Thanks to its versatility, biocompatibility, and biodegradability, β-CD is widespread in many research and industrial applications. In this review, we summarize the role of β-CD and its derivatives in the textile industry. First, we present some general physicochemical characteristics, followed by its application in the areas of dyeing, finishing, and wastewater treatment. The review covers the role of β-CD as an auxiliary agent in dyeing, and as a matrix for dye adsorption until chemical modifications are applied as a finishing agent. Finally, new perspectives about its use in textiles, such as in smart materials for microbial control, are presented.

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“…The process can efficiently describe the complex formation between CNC-CD and surfactants. In this case, an improved understanding of CD interactions with surfactants and lipids would enable better strategies for drug encapsulation with CDs [76].…”

Section: Drug Delivery Systemsmentioning

confidence: 99%

Surfactant for better tomorrow: applied aspect of surfactant aggregates from laboratory to industry

et al. 2019

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Surfactant is a special kind of amphiphilic compound composed of water-loving and hating parts. The remarkable physical properties like interfacial tension, wettability, emulsifying and dispersing ability make the surfactant accessible for numerous applications from laboratory to commercial products. In recent years, the commercial applications of surfactant have led to greater relevance on account of the environmental concerns and market pressures of this compound. The utility of surfactants in global market increases steadily since its formulation with several beneficial aspects in pharmaceutical, detergent, cosmetic, paint, food science, gas hydrate, nanotechnology, petroleum recovery, bioremediation, chemical transformation and drug delivery. This review briefly discusses the applied aspect of surfactants in diverse area as well as catalytic effect of micelle in organic reactions from the recent literature survey. The trend of increasing use of bioderived surfactants in the modern field of research is also considered in this report. The recent advancement of surfactant-based organic transformations has been emphasized with the role of surfactant aggregates in course of different organic reactions.

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β-Cyclodextrin-Functionalized Cellulose Nanocrystals and Their Interactions with Surfactants

Cited by 16 publications

References 35 publications

pH-responsive polymer-based biomacromolecule nanosponges as biodegradable carriers for DOX delivery

pH-responsive polymer-based biomacromolecule nanosponges as biodegradable carriers for DOX delivery

The Role of β-Cyclodextrin in the Textile Industry—Review

Surfactant for better tomorrow: applied aspect of surfactant aggregates from laboratory to industry

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