α,α-Trehalose-based polyacetals and macrocyclic acetals

Kukowka, Sylwia; Maślińska-Solich, Jolanta

doi:10.1016/j.carbpol.2009.12.008

Cited by 8 publications

(6 citation statements)

References 15 publications

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“…An increasing interest has been shown in the past few years for the design of linear polyacetals. [14][15][16][17][18][19][20][21][22][23][24] Heller et al first reported the synthesis of linear and cross-linked polyacetal by condensation of polyols with divinyl ethers. 14 This reaction has been applied more recently by Tomlinson et al to the synthesis of water-soluble, biocompatible, amino-functionalized polyacetals, suitable for drug conjugation (Fig.…”

Section: Linear Bioerodible Polymers and Their Use In Microparticles ...mentioning

confidence: 99%

Acid-degradable polymers for drug delivery: a decade of innovation

2013

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Polymers that start degrading under acidic conditions are increasingly investigated as a pathway to trigger the release of drugs once the drug carrier reached the slightly acidic tumour environment or after the drug carrier has been taken up by cells, resulting in the localization of the polymer in the acidic endosomes and lysosomes. The advances in the design of acid-degradable polymers and drug delivery systems have been summarized and discussed in this review article. Various acid-labile groups such as acetals, orthoester, hydrazones, imines and cis-aconityl, that can undergo cleavage in slightly acidic conditions, have been employed to create polymer architectures or polymer-drug conjugates that can degrade under lysosomal and endosomal conditions, triggering the fast release of drugs or DNA.

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Section: Linear Bioerodible Polymers and Their Use In Microparticles ...mentioning

confidence: 99%

Acid-degradable polymers for drug delivery: a decade of innovation

2013

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“…However, this methodology presented some clear disadvantages such as harsh polymerization conditions, low (8.5 kDa) maximum molecular weight (MW) obtained, no glass transition temperature ( T g ) found up to the decomposition temperature ( T d ) of 325 °C, 32 and the formation of a mixture of polymers with different end groups or even cyclization. 33 To overcome these drawbacks, Teramoto et al designed a different strategy to regioselectively modify trehalose with 4-allyl-oxybenzaldehyde and then polymerize by hydrosilylation with SiH-terminated dimethylsiloxane oligomers. 34 Polymers 3 with a MW up to 50 kDa were obtained when the mixture was heated at 80 °C for 72 h. Yields were generally high (ca.…”

Section: Polymerization Strategiesmentioning

confidence: 99%

Synthesis and Application of Trehalose Materials

Vinciguerra

Gelb

Maynard

2022

JACS Au

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Trehalose is a naturally occurring, nonreducing disaccharide that is widely used in the biopharmaceutical, food, and cosmetic industries due to its stabilizing and cryoprotective properties. Over the years, scientists have developed methodologies to synthesize linear polymers with trehalose units either in the polymer backbone or as pendant groups. These macromolecules provide unique properties and characteristics, which often outperform trehalose itself. Additionally, numerous reports have focused on the synthesis and formulation of materials based on trehalose, such as nanoparticles, hydrogels, and thermoset networks. Among many applications, these polymers and materials have been used as protein stabilizers, as gene delivery systems, and to prevent amyloid aggregate formation. In this Perspective, recent developments in the synthesis and application of trehalose-based linear polymers, hydrogels, and nanomaterials are discussed, with a focus on utilization in the biomedical field.

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“…Recent studies include the preparation of α,α′-trehalose-based polymer networks through vinyl benzyl etherification and subsequent thermal curing reactions [ 32 ] or through allyl etherification and subsequent thiol-ene photopolymerization [ 33 ]. Moreover, linear polymers were synthesized using polyaddition of diamino-type α,α′-trehalose with diisocyanates [ 34 ], enzymatic or chemoenzymatic reactions [ 35 , 36 ], acetalization reactions with dialdehydes [ 37 , 38 ], hydrosilylation [ 39 ], Diels–Alder [ 40 ] and azide–alkyne Huisgen reactions.…”

Section: Introductionmentioning

confidence: 99%

Modified α,α′-trehalose andd-glucose: green monomers for the synthesis of vinyl copolymers

et al. 2018

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Allyl saccharide/vinyl copolymers were synthesized using renewable feedstocks (α,α′-trehalose and d-glucose) to obtain ‘green monomers’. Properly designed synthetic procedures were used to obtain copolymers with high purity and without protection/deprotection steps in agreement with the principles of green chemistry and industrial sustainability. The use of saccharide derivatives as monomers allowed products to be obtained that showed high affinity and compatibility for the cellulosic substrates, like paper or wood, and that were suitable for applications like adhesion or consolidation in the field of cultural heritage. All reaction products were characterized by FT-IR and NMR spectroscopies and SEC analyses, while thermal properties were evaluated by DSC analyses.

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α,α-Trehalose-based polyacetals and macrocyclic acetals

Cited by 8 publications

References 15 publications

Acid-degradable polymers for drug delivery: a decade of innovation

Acid-degradable polymers for drug delivery: a decade of innovation

Synthesis and Application of Trehalose Materials

Modified α,α′-trehalose andd-glucose: green monomers for the synthesis of vinyl copolymers

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