Synthesis of Poly(ethylene glycol)-based Hydrogels via Amine-Michael Type Addition with Tunable Stiffness and Postgelation Chemical Functionality

Zhang, Zhenfang; Loebus, Axel; Vicente, G.; Ren, Fang; Arafeh, Manar; Ouyang, Zhengbiao; Lensen, Marga C.

doi:10.1021/cm500203j

Cited by 44 publications

(58 citation statements)

References 26 publications

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“…Next we tested in vivo amino acid synthesis and incorporation in a relevant application: we investigated the feasibility of attaching Sac‐containing proteins to novel thiol‐functionalized hydrogels (synthetic protocol in the Supporting Information) . Hydrogels polymerized by the thiol‐ene reaction are of special interest for the encapsulation and delivery of proteins for therapeutic purposes .…”

Section: Figurementioning

confidence: 99%

“…[30,31] Next we tested in vivo amino acid synthesis and incorporation in ar elevant application:w ei nvestigated the feasibility of attaching Sac-containing proteinst on ovel thiol-functionalized hydrogels (synthetic protocol in the Supporting Information). [37] Hydrogels polymerized by the thiol-ene reactiona re of special interestf or the encapsulation and delivery of proteins for therapeutic purposes. [38,39] We chose cysteine-free superfolder GFP (cfsfGFP) with Sac in place of Arg at position2a sm odel pro- [36] and the assumed structure of SacRS.A pparently,m utation C348W blocksthe lower part of the amino-acid-binding pocket (clashing with the Pyl moiety)and thusp reventsa ctivationof Pyl but allowst he accommodation of Sac.…”

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confidence: 99%

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Design of S‐Allylcysteine in Situ Production and Incorporation Based on a Novel Pyrrolysyl‐tRNA Synthetase Variant

Exner

Kuenzl

et al. 2016

ChemBioChem

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The noncanonical amino acid S-allyl cysteine (Sac) is one of the major compounds of garlic extract and exhibits ar ange of biological activities. It is also as mall bioorthogonal alkene tag capable of undergoing controlled chemical modifications, such as photoinduced thiol-ene coupling or Pd-mediated deprotection. Its small size guarantees minimal interference with protein structure and function. Here, we report as imple protocol efficiently to couple in-situ semisynthetic biosynthesis of Sac and its incorporation into proteins in response to amber (UAG) stop codons. We exploitedt he exceptional malleability of pyrrolysyl-tRNA synthetase (PylRS) and evolved an S-allylcysteinyltRNA synthetase (SacRS) capable of specifically acceptingt he small, polar amino acid instead of its long andb ulky aliphatic natural substrate. We succeeded in generating an ovel and inexpensive strategy for the incorporation of af unctionally versatile amino acid. This will help in the conversiono fo rthogonal translation from as tandard technique in academic research to industrial biotechnology.

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Section: Figurementioning

confidence: 99%

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confidence: 99%

Design of S‐Allylcysteine in Situ Production and Incorporation Based on a Novel Pyrrolysyl‐tRNA Synthetase Variant

Exner

Kuenzl

et al. 2016

ChemBioChem

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“…There was no significant effect of changing diacrylate from TEGDA to PEGDA ( M n ‐250) on gelation time as there was no reactivity difference between the diacrylates of TEG and PEG. However, thiol‐Michael additions are faster than aza‐Michael additions due to the higher nucleophilicity of thiols compared to amines . Therefore, one can select the tetra‐functional thiol‐counterpart to achieve faster gelation compared to the gelation time of present PAMAM based hydrogel systems.…”

Section: Resultsmentioning

confidence: 99%

pH and reduction dual‐stimuli‐responsive PEGDA/PAMAM injectable network hydrogels via aza‐michael addition for anticancer drug delivery

Patil

Shinde

Misra

2018

J. Polym. Sci. Part A: Polym. Chem.

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A pH and reduction dual‐stimuli‐responsive PEGDA/PAMAM injectable network hydrogel containing “acetals” as pH‐sensitive groups and “disulfides” as reducible linkages was designed and synthesized via aza‐Michael addition reaction between PAMAM and PEGDA diacrylates. The pore size and swelling ratio of hydrogels was varied from 14 ± 3 to 19 ± 4 μm and 214 ± 13 to 300 ± 19 μm, respectively, with varying ethylene glycol repeating units in diacrylates. The swelling ratio of PEGDA/PAMAM network hydrogel increased with increase in the molecular weight of PEG and with decrease in pH. The presence of different cationizable amino‐functionalities in PEGDA/PAMAM network hydrogel helped to enhance the swelling ability of hydrogel under the acidic conditions. The continuous increase in metabolically active live HeLa cells with time in MTT assay implied biocompatibility/noncytotoxicity of the synthesized PEGDA/PAMAM injectable network hydrogel. Furthermore, the prepared PEGDA/PAMAM hydrogel showed higher degradation at lower pH and at higher concentration of DTT. The burst release of doxorubicin from PEGDA/PAMAM hydrogel under the environment of the lower pH and in presence of DTT compared to the release at normal physiological pH and in absence of DTT suggested the potential ability of this model hydrogel system for targeted and selective anticancer drug release at tumor tissues. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2080–2095

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“…Depending on the desired structure and the targeted application, hydrogels have been synthesized employing versatile chemistries, such as radical polymerization, the formation of carbon-nitrogen double bond, 73, 74 Michael-type addition reaction, 75, 76 thiol-ene photochemistry, 77, 78 and several types of orthogonal chemistries, 79–81 and enzyme-catalyzed reaction. 82, 83 …”

Section: Chemical Approaches To Hydrogel Synthesismentioning

confidence: 99%

“…124 A frequently used Michael type reaction for hydrogel synthesis is the addition of thiols to α,β-unsaturated carbonyls (such as maleimide, acrylate, acrylamide or vinylsulfone) because it occurs rapidly under mild reaction conditions with a high conversion. 76, 125–127 There has been considerable research in developing synthetic ECM using thiolated HA (HA-SH) and HA or PEG carrying reactive double bonds. For instance, injectable hydrogels formed from HA-SH and 4-arm PEG vinylsulfone were prepared for potential cartilage tissue engineering.…”

Section: Chemical Approaches To Hydrogel Synthesismentioning

confidence: 99%

Chemical synthesis of biomimetic hydrogels for tissue engineering

2017

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Owing to the high water content, porous structure, biocompatibility and tissue-like viscoelasticity, hydrogels have become attractive and promising biomaterials for use in drug delivery, 3D cell culture and tissue engineering applications. Various chemical approaches have been developed for hydrogel synthesis using monomers or polymers carrying reactive functional groups. For in vivo tissue repair and in vitro cell culture purposes, it is desirable that the crosslinking reactions occur under mild conditions, do not interfere with biological processes and proceed at high yield with exceptional selectivity. Additionally, the cross-linking reaction should allow straightforward incorporation of bioactive motifs or signaling molecules, at the same time, providing tunability of the hydrogel microstructure, mechanical properties, and degradation rates. In this review, we discuss various chemical approaches applied to the synthesis of complex hydrogel networks, highlighting recent developments from our group. The discovery of new chemistries and novel materials fabrication methods will lead to the development of the next generation biomimetic hydrogels with complex structures and diverse functionalities. These materials will likely facilitate the construction of engineered tissue models that may bridge the gap between 2D experiments and animal studies, providing preliminary insight prior to in vivo assessments.

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Synthesis of Poly(ethylene glycol)-based Hydrogels via Amine-Michael Type Addition with Tunable Stiffness and Postgelation Chemical Functionality

Cited by 44 publications

References 26 publications

Design of S‐Allylcysteine in Situ Production and Incorporation Based on a Novel Pyrrolysyl‐tRNA Synthetase Variant

Design of S‐Allylcysteine in Situ Production and Incorporation Based on a Novel Pyrrolysyl‐tRNA Synthetase Variant

pH and reduction dual‐stimuli‐responsive PEGDA/PAMAM injectable network hydrogels via aza‐michael addition for anticancer drug delivery

Chemical synthesis of biomimetic hydrogels for tissue engineering

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