Biodegradable PEG Hydrogels Cross-linkedUsing Biotin-Avidin Interactions

2010 ◽  
Vol 63 (10) ◽  
pp. 1413 ◽  
Author(s):  
Yingkai Liu ◽  
Jingquan Liu ◽  
Jiangtao Xu ◽  
Shengyu Feng ◽  
Thomas P. Davis
Keyword(s):  
Disulfide Bonds ◽  
Condensation Reaction ◽  
Cross Linking ◽  
Toxic Chemical ◽  
Poly Ethylene Glycol ◽  
Peg Hydrogels ◽  
Pharmaceutical Applications ◽  
The Common ◽  
Poly Ethylene ◽  
Chemical Cross Linking

Poly(ethylene glycol) (PEG) hydrogels are water-swellable, non-toxic, non-immunogenic, and biocompatible. In this paper, we describe the generation of biodegradable PEG hydrogels by cross-linking biotinylated PEG oligomers containing intrinsic disulfide bonds via biotin-avidin interactions. The biotinylated PEG oligomers were synthesized by the condensation reaction between PEG and 3,3′-dithiodipropionic acid, followed by the reaction with biotin. This methodology obviates the need for potentially toxic chemical cross-linking agents that are usually used in the common preparation of hydrogels. Therefore it may be particularly useful in biomedical or pharmaceutical applications.

scholarly journals Mechanically Reinforced Gelatin Hydrogels by Introducing Slidable Supramolecular Cross-Linkers

Polymers ◽  
2019 ◽  
Vol 11 (11) ◽  
pp. 1787 ◽  
Author(s):  
Dae Hoon Lee ◽  
Atsushi Tamura ◽  
Yoshinori Arisaka ◽  
Ji-Hun Seo ◽  
Nobuhiko Yui
Keyword(s):  
Mechanical Properties ◽  
Stress Concentration ◽  
Cross Linking ◽  
Supramolecular Polymer ◽  
Poly Ethylene Glycol ◽  
Physical Force ◽  
Adhesive Material ◽  
Cell Adhesive ◽  
Poly Ethylene ◽  
Chemical Cross Linking

Tough mechanical properties are generally required for tissue substitutes used in regeneration of damaged tissue, as these substitutes must be able to withstand the external physical force caused by stretching. Gelatin, a biopolymer derived from collagen, is a biocompatible and cell adhesive material, and is thus widely utilized as a component of biomaterials. However, the application of gelatin hydrogels as a tissue substitute is limited owing to their insufficient mechanical properties. Chemical cross-linking is a promising method to improve the mechanical properties of hydrogels. We examined the potential of the chemical cross-linking of gelatin hydrogels with carboxy-group-modified polyrotaxanes (PRXs), a supramolecular polymer comprising a poly(ethylene glycol) chain threaded into the cavity of α-cyclodextrins (α-CDs), to improve mechanical properties such as stretchability and toughness. Cross-linking gelatin hydrogels with threading α-CDs in PRXs could allow for freely mobile cross-linking points to potentially improve the mechanical properties. Indeed, the stretchability and toughness of gelatin hydrogels cross-linked with PRXs were slightly higher than those of the hydrogels with the conventional chemical cross-linkers 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC)/N-hydroxysuccinimide (NHS). In addition, the hysteresis loss of gelatin hydrogels cross-linked with PRXs after repeated stretching and relaxation cycles in a hydrated state was remarkably improved in comparison with that of conventional cross-linked hydrogels. It is considered that the freely mobile cross-linking points of gelatin hydrogels cross-linked with PRXs attenuates the stress concentration. Accordingly, gelatin hydrogels cross-linked with PRXs would provide excellent mechanical properties as biocompatible tissue substitutes exposed to a continuous external physical force.

On the 3D Correlation between Myofibroblast Shape and Contraction

2021 ◽  
Author(s):  
Alex Khang ◽  
Emma Lejeune ◽  
Ali Abbaspour ◽  
Daniel Howsmon ◽  
Michael Sacks
Keyword(s):  
Cell Shape ◽  
Interstitial Cell ◽  
Stable State ◽  
Stress Fiber ◽  
Poly Ethylene Glycol ◽  
Critical Feature ◽  
Peg Hydrogels ◽  
Poly Ethylene ◽  
And Function ◽  
The Relationship

Abstract Cell shape is known to correlate closely with stress-fiber geometry and function, and is thus a critical feature of cell biophysical state. However, the relationship between myofibroblast shape and contraction is complex, even as well in regards to steady-state contractile level (basal tonus). At present, the relationship between myofibroblast shape and basal tonus in 3D is poorly understood. Herein, we utilize the aortic valve interstitial cell (AVICs) as a representative myofibroblast to investigate the relationship between basal tonus and overall cell shape. AVICs were embedded within 3D poly (ethylene glycol) (PEG) hydrogels containing degradable peptide crosslinkers, adhesive peptide sequences, and sub-micron fluorescent micro-spheres to track the local displacement field. We then developed a methodology to evaluate the correlation between overall AVIC shape and basal tonus induced contraction. We computed a volume averaged stretch tensor <U> for the volume occupied by the AVIC, which had three distinct eigenvalues (1.08, 0.99, and 0.89), suggesting that AVIC shape is a result of anisotropic contraction. Furthermore, the direction of maximum contraction correlated closely with the longest axis of a bounding ellipsoid enclosing the AVIC. As gel--imbedded AVIC are known to be in a stable state by three days of incubation used herein, this finding suggests that the overall quiescent AVIC shape is driven by the underlying stress-fiber directional structure and possibly contraction level.

Therapeutic effects of boronate ester cross-linked injectable hydrogels for the treatment of hepatocellular carcinoma

2021 ◽  
Author(s):  
Jae Min Jung ◽  
Seong Han Kim ◽  
V. H. Giang Phan ◽  
Thavasyappan Thambi ◽  
Doo Sung Lee
Keyword(s):  
Hepatocellular Carcinoma ◽  
Ethylene Glycol ◽  
Therapeutic Effects ◽  
Poly Ethylene Glycol ◽  
Injectable Hydrogels ◽  
High Incidence ◽  
High Incidence Rate ◽  
The Common ◽  
Poly Ethylene ◽  
Responsive Hydrogels

Hepatocellular carcinoma is the common malignant with a high incidence rate and responsible for the highest cause of cancer-related deaths. Herein, we developed a thermo-responsive hydrogels comprised of poly(ε-caprolactone-co-lactide)-b-poly(ethylene glycol)-b-poly(ε-caprolactone-co-lactide...

Cross-linking of cellulose and poly(ethylene glycol) with citric acid

2015 ◽  
Vol 90 ◽  
pp. 21-24 ◽  
Author(s):  
Pamela de Cuadro ◽  
Tiina Belt ◽  
Katri S. Kontturi ◽  
Mehedi Reza ◽  
Eero Kontturi ◽  
...  
Keyword(s):  
Citric Acid ◽  
Ethylene Glycol ◽  
Cross Linking ◽  
Poly Ethylene Glycol ◽  
Poly Ethylene

Preparation and Properties of a Hydrolytically Stable Cyclooctyne-Containing Polymer

Synlett ◽  
2018 ◽  
Vol 29 (19) ◽  
pp. 2535-2541
Author(s):  
Alex Adronov ◽  
Kelvin Li ◽  
Stuart McNelles
Keyword(s):  
Molecular Weight ◽  
Ethylene Glycol ◽  
Monomethyl Ether ◽  
Phenylene Vinylene ◽  
Cross Linking ◽  
Poly Ethylene Glycol ◽  
Ethylene Glycol Monomethyl Ether ◽  
Glycol Monomethyl Ether ◽  
Poly Ethylene

A poly[(phenylene vinylene)-co-dibenzocyclooctyne] polymer prepared by Wittig polymerization chemistry between dibenzocyclooctyne bisaldehyde [DIBO-(CHO)2] and bis(triethyleneglycol)phenylbis(tributylphosphonium) dibromide is reported. The resulting polymer exhibits moderate molecular weight (Mn: 10.5 kDa, Mw: 21.3 kDa, Ð: 2.02) and is fluorescent. It could be readily functionalized by strain-promoted alkyne-azide cycloadditon with different azides, and fluorescence of the polymer was preserved after functionalization. Grafting azide-terminated 5 kDa poly(ethylene glycol) monomethyl ether chains drastically affected the solubility of the polymer. Cross-linking the polymer with poly(ethylene glycol) that was terminated at both ends with azide groups gave access to a fluorescent organogel that could be dried and reswollen with water to form a hydrogel.

scholarly journals Orthogonal click reactions enable the synthesis of ECM-mimetic PEG hydrogels without multi-arm precursors

2018 ◽  
Vol 6 (30) ◽  
pp. 4929-4936 ◽  
Author(s):  
Faraz Jivan ◽  
Natalia Fabela ◽  
Zachary Davis ◽  
Daniel L. Alge
Keyword(s):  
Tissue Engineering ◽  
Ethylene Glycol ◽  
Click Chemistry ◽  
Bioactive Peptides ◽  
Poly Ethylene Glycol ◽  
Click Reactions ◽  
Peg Hydrogels ◽  
Poly Ethylene

A two-step, click chemistry approach to create user-defined hydrogels consisting of poly(ethylene glycol) and bioactive peptides without the use of multi-arm precursors for tissue engineering.

scholarly journals A fast and versatile cross-linking strategy via o-phthalaldehyde condensation for mechanically strengthened and functional hydrogels

2020 ◽  
Author(s):  
Zhen Zhang ◽  
Chaoliang He ◽  
Yan Rong ◽  
Hui Ren ◽  
Tianran Wang ◽  
...  
Keyword(s):  
Condensation Reaction ◽  
Building Blocks ◽  
Order Rate Constant ◽  
Cross Linking ◽  
Click Reactions ◽  
Oxime Formation ◽  
Cross Links ◽  
Poly Ethylene ◽  
Molecule Model ◽  
First Time

Abstract Fast and catalyst-free cross-linking strategy is of great significance for construction of covalently cross-linked hydrogels. Here, we report the condensation reaction between o-phthalaldehyde (OPA) and N-nucleophiles (primary amine, hydrazide and aminooxy) for hydrogel formation for the first time. When four-arm poly(ethylene glycol) (4aPEG) capped with OPA was mixed with various N-nucleophile-terminated 4aPEG as building blocks, hydrogels were formed with superfast gelation rate, higher mechanical strength and markedly lower critical gelation concentrations, compared to benzaldehyde-based counterparts. Small molecule model reactions indicate the key to these cross-links is the fast formation of heterocycle phthalimidine product or isoindole (bis)hemiaminal intermediates, depending on the N-nucleophiles. The second-order rate constant for the formation of phthalimidine linkage (4.3 M−1 s−1) is over 3000 times and 200 times higher than those for acylhydrazone and oxime formation from benzaldehyde, respectively, and comparable to many cycloaddition click reactions. Based on the versatile OPA chemistry, various hydrogels can be readily prepared from naturally derived polysaccharides, proteins or synthetic polymers without complicated chemical modification. Moreover, biofunctionality is facilely imparted to the hydrogels by introducing amine-bearing peptides via the reaction between OPA and amino group.

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