Amino acid modified cellulose whiskers

Cateto, C.A.; Ragauskas, Arthur J.

doi:10.1039/c1ra00647a

Cited by 35 publications

(10 citation statements)

References 20 publications

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“… 51 In 2011, Cateto et al modified cellulose nanowhiskers with L-leucine by a two-step process involving the reaction between CNCs and Fmoc-protected L-leucine followed by the removal of the Fmoc protecting group. 52 The reaction was performed with 4-dimethylaminopyridine (DMAP) as a base catalyst and N-ethyl-N’-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC HCl), as a coupling agent.…”

Section: Surface Chemistry Of Nanocellulosementioning

confidence: 99%

<p>Surface-Modified Nanocellulose for Application in Biomedical Engineering and Nanomedicine: A Review</p>

Tortorella¹,

Buratti²,

Maturi³

et al. 2020

IJN

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Presently, a plenty of concerns related to the environment are due to the overuse of petroleum-based chemicals and products; the synthesis of functional materials, starting from the natural sources, is the current trend in research. The interest for nanocellulose has recently increased in a huge range of fields, from the material science to the biomedical engineering. Nanocellulose gained this leading role because of several reasons: its natural abundance on this planet, the excellent mechanical and optical features, the good biocompatibility and the attractive capability of undergoing surface chemical modifications. Nanocellulose surface tuning techniques are adopted by the high reactivity of the hydroxyl groups available; the chemical modifications are mainly performed to introduce either charged or hydrophobic moieties that include amination, esterification, oxidation, silylation, carboxymethylation, epoxidation, sulfonation, thiol- and azido-functional capability. Despite the several already published papers regarding nanocellulose, the aim of this review involves discussing the surface chemical functional capability of nanocellulose and the subsequent applications in the main areas of nanocellulose research, such as drug delivery, biosensing/bioimaging, tissue regeneration and bioprinting, according to these modifications. The final goal of this review is to provide a novel and unusual overview on this topic that is continuously under expansion for its intrinsic sophisticated properties.

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Section: Surface Chemistry Of Nanocellulosementioning

confidence: 99%

<p>Surface-Modified Nanocellulose for Application in Biomedical Engineering and Nanomedicine: A Review</p>

Tortorella¹,

Buratti²,

Maturi³

et al. 2020

IJN

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“…No noticeably cytotoxic effect was observed, rendering modified cellulose nanocrystals as promising candidates for bioimaging and drug delivery systems. Anchoring of L-leucine moieties to cellulose nanocrystals allowing the creation of a binding site to which drugs or targeting molecules can be attached was also reported (Cateto and Ragauskas, 2011). TEMPO-oxidized MFC was coupled with fluorescent amino acids using a two-step procedure (Barazzouk and Daneault, 2011).…”

Section: Fluorescently Labeled Nanocellulosementioning

confidence: 99%

5 Chemical modification of nanocellulose

Dufresne¹

2012

Nanocellulose

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Extensive studies have been conducted on the utilization of cellulose nanocrystals, microfibrillated cellulose and bacterial cellulose as reinforcements in polymer nanocomposites. Efficiency of nanofiller dispersion in the matrix and adequacy of nanofiller-matrix interfacial interactions are widely known to critically affect material physical and mechanical properties. Because of its inherent hydrophilicity, it is difficult to achieve a good dispersion level of nanocellulose reinforcements in water-insoluble or non-water dispersible polymer matrices. This limitation stems primarily from the high affinity of nanocellulose for water and its inability to disperse readily in organic solvents. Cellulosic nanoparticles are characterized by hydrogen bonding-induced aggregation which is magnified because of their nanosized and fibrillar structures. To prevent self-aggregation (sometimes referred to as hornification) and promote efficient dispersion in non-aqueous media, the surface of cellulosic nanoparticles can be modified with hydrophobic compounds using covalent and non-covalent coupling techniques. A wide variety of chemical modification techniques, including coupling hydrophobic small molecules, grafting polymers and oligomers, and adsorbing hydrophobic compounds to surface hydroxyl groups of cellulosic nanoparticles, can be employed. Besides the problem of dispersibility with polymeric matrices, improved nanofiller-matrix interaction is expected to enhance the stress transfer from the matrix to the dispersed phase and then improve the loadbearing capability of the material. Moreover, the surface of the nanoparticles can be tailored to impart specific functionality to nanocellulose.

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“…These modifications are beneficial in a variety of medical applications, in particular as wound dressing materials. Cateto et al [21] reported the functionalisation of BC with L-leucine using Fmoc-L-leucine and cellulose whiskers to enhance cell-adhesive structures, hydrophobic drug carriers and gas separation membranes. Kalaskar et al [17] reported the characterisation of cellulose fibre surfaces by modification using three different amino acids with variable side chain groups using solid phase peptide synthesis.…”

Section: Introductionmentioning

confidence: 99%

Mechanical properties of TEMPO-oxidised bacterial cellulose-amino acid biomaterials

Pahlevan

Toivakka

Alam

2018

European Polymer Journal

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Amino acid functionalised bacterial cellulose is a non-toxic biocompatible material, which can be further modified with active groups and nanoparticles for various biomedical applications. Many studies have focused mainly on the chemical and biomedical characterisation of modified bacterial cellulose; however, the mechanical performance of these materials remains undetermined. In this paper, we investigate the mechanical performance of amino acid modified TEMPO-oxidised bacterial cellulose (TOBC-AA). Highly crystalline bacterial cellulose was initially oxidised via TEMPO-mediated oxidation and amino acids-specifically glycine, alanine and proline-were grafted to TOBC via EDAC/NHS coupling agent. Manufactured materials have been tested and compared with pure bacterial cellulose and our recently studied monomeric amino acid bio-glues. Under tensile loading, the rigid crystalline structure of the copolymer has a slightly higher strength and toughness compared to pure BC, however its adhesive properties were significantly lower than those of monomeric amino acids. The side chains on TOBC-AA physically interlock under the conditions of shear; however amino acids grafted to BC lack mobility and the ability to form H-bonds, in contrast to monomeric amino acid such as glycine and alanine. Table 1-List of abbreviations List of abbreviation BC Bacterial cellulose TOBC TEMPO oxidised bacterial cellulose AA Amino Acid Ala Alanine Gly Glycine Pro Proline BC-AA Bacterial cellulose based composite with monomeric amino acid TOBC-AA Amino acid modified TEMPO oxidised bacterial cellulose TEMPO 2,2,6,6-tetramethylpiperidine-1-oxyl NHS N-hydroxy-succinimide EDAC N-ethyl-N-(3-dimethylaminopropyl)-carbodiimide hydrochloride

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Amino acid modified cellulose whiskers

Cited by 35 publications

References 20 publications

<p>Surface-Modified Nanocellulose for Application in Biomedical Engineering and Nanomedicine: A Review</p>

<p>Surface-Modified Nanocellulose for Application in Biomedical Engineering and Nanomedicine: A Review</p>

5 Chemical modification of nanocellulose

Mechanical properties of TEMPO-oxidised bacterial cellulose-amino acid biomaterials

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