Multiple grafting to enzymatically synthesized polyesters

Bilal, Muhammad Humayun; Alaneed, Razan; Steiner, Jonas; Mäder, Karsten; Pietzsch, Markus; Kreßler, Jörg

doi:10.1016/bs.mie.2019.04.031

Cited by 8 publications

(4 citation statements)

References 56 publications

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“…In a typical procedure to synthesize α,ω-bis-succinyl poly(ethylene glycol) (Suc-PEG n -Suc) (with n = 9, 23, 45) and α-methoxy,ω-succinyl poly(ethylene glycol) 12 (mPEG 12 -Suc), PEG was acylated by reaction with succinic anhydride through a procedure described elsewhere [ 53 , 54 ]. For the synthesis of mPEG 12 -Suc, mPEG 12 of molar mass 550 g·mol −1 was used, while for the synthesis of Suc-PEG n -Suc, OH-PEG n -OH having molar mass of 400 g·mol −1 , 1000 g·mol −1 , and 2000 g·mol −1 were used, respectively.…”

Section: Methodsmentioning

confidence: 99%

Polymer Networks Synthesized from Poly(Sorbitol Adipate) and Functionalized Poly(Ethylene Glycol)

Rashid

Golitsyn

Bilal

et al. 2021

Gels

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Polymer networks were prepared by Steglich esterification using poly(sorbitol adipate) (PSA) and poly(sorbitol adipate)-graft-poly(ethylene glycol) mono methyl ether (PSA-g-mPEG12) copolymer. Utilizing multi-hydroxyl functionalities of PSA, poly(ethylene glycol) (PEG) was first grafted onto a PSA backbone. Then the cross-linking of PSA or PSA-g-mPEG12 was carried out with disuccinyl PEG of different molar masses (Suc-PEGn-Suc). Polymers were characterized through nuclear magnetic resonance (NMR) spectroscopy, gel permeation chromatography (GPC), and differential scanning calorimetry (DSC). The degree of swelling of networks was investigated through water (D2O) uptake studies, while for detailed examination of their structural dynamics, networks were studied using 13C magic angle spinning NMR (13C MAS NMR) spectroscopy, 1H double quantum NMR (1H DQ NMR) spectroscopy, and 1H pulsed field gradient NMR (1H PFG NMR) spectroscopy. These solid state NMR results revealed that the networks were composed of a two component structure, having different dipolar coupling constants. The diffusion of solvent molecules depended on the degree of swelling that was imparted to the network by the varying chain length of the PEG based cross-linking agent.

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Section: Methodsmentioning

confidence: 99%

Polymer Networks Synthesized from Poly(Sorbitol Adipate) and Functionalized Poly(Ethylene Glycol)

Rashid

Golitsyn

Bilal

et al. 2021

Gels

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“…35,36 To improve the yields in the production of bridged disaccharide derivatives, alternative conditions were evaluated using as a model the synthesis of 16a from the glycosyl azide 5a and the thioglyco acid 13b (Table 3). The Steglich amidation was Chart 1 Carboxylic acids selected for amidation reactions with glycosyl amines 2a-c. attempted, since the use of N,N-dimethylaminopyridine (DMAP) and carbodiimides was reported to facilitate the formation of esters [37][38][39] or amides 40,41 of sterically hindered acids or lowreactivity nucleophiles (alcohols or amines).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli

Traverssi,

Manzano,

Varela

et al. 2024

RSC Adv.

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“…To achieve a higher swellability of the hydrogels, PSA was grafted to poly(ethylene glycol) (PEG). For the grafting of PSA to PEG, mPEG 550 was modified by acylation with succinic anhydride via a procedure described elsewhere [24,90] to obtain monofunctional PEG (Supplementary Materials Figure S4). 1 H-NMR ((400 MHz, CDCl 3 ) δ (ppm): 4.25-4.21 (m, 2H), 3.68-3.51 (m, 50H), 3.35 (s, 3H), 2.67-2.56 (m, 4H)).…”

Section: Polymers and Hydrogel Synthesesmentioning

confidence: 99%

“…Similarly, the M n of PSA-g-mPEG utilized for the stability study was 16,000 g•mol −1 , while the M n of PSA-g-mPEG utilized for the preparation of hydrogels was 17,250 g•mol −1 (Supplementary Materials Figures S3 and S1b The next step was to crosslink the PSA-g-mPEG polymer through a bifunctional PEG, which took place by first synthesizing bifunctional PEG. The PEG of three different molar masses (PEG-400, PEG-1000, and PEG-2000) was acylated on both sides with succinic anhydride through a procedure described elsewhere [24,90,91]. In the last step, hydrogels were formed by esterifying secondary hydroxyl groups from PSA-g-mPEG and terminal carboxyl groups from bifunctional PEG (Supplementary Materials Figures S5-S7).…”

Section: Polymers and Hydrogel Synthesesmentioning

confidence: 99%

Development of Poly(sorbitol adipate)-g-poly(ethylene glycol) Mono Methyl Ether-Based Hydrogel Matrices for Model Drug Release

Rashid,

Lucas,

Busse

et al. 2023

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Hydrogels were prepared by Steglich esterification and by crosslinking pre-synthesized poly(sorbitol adipate)-graft-poly(ethylene glycol) mono methyl ether (PSA-g-mPEG) using different-chain-length-based disuccinyl PEG. PSA and PSA-g-mPEG were investigated for polymer degradation as a function of time at different temperatures. PSA-g-mPEG hydrogels were then evaluated for their most crucial properties of swelling that rendered them suitable for many pharmaceutical and biomedical applications. Hydrogels were also examined for their Sol-Gel content in order to investigate the degree of cross-linking. Physical structural parameters of the hydrogels were theoretically estimated using the modified Flory–Rehner theory to obtain approximate values of polymer volume fraction, the molecular weight between two crosslinks, and the mesh size of the hydrogels. X-ray diffraction was conducted to detect the presence or absence of crystalline regions in the hydrogels. PSA-g-mPEG hydrogels were then extensively examined for higher and lower molecular weight solute release through analysis by fluorescence spectroscopy. Finally, the cytotoxicity of the hydrogels was also investigated using a resazurin reduction assay. Experimental results show that PSA-g-mPEG provides an option as a biocompatible polymer to be used for pharmaceutical applications.

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Multiple grafting to enzymatically synthesized polyesters

Cited by 8 publications

References 56 publications

Polymer Networks Synthesized from Poly(Sorbitol Adipate) and Functionalized Poly(Ethylene Glycol)

Polymer Networks Synthesized from Poly(Sorbitol Adipate) and Functionalized Poly(Ethylene Glycol)

Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli

Development of Poly(sorbitol adipate)-g-poly(ethylene glycol) Mono Methyl Ether-Based Hydrogel Matrices for Model Drug Release

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