Online citations, reference lists, and bibliographies.
← Back to Search

Click Hydrogels, Microgels And Nanogels: Emerging Platforms For Drug Delivery And Tissue Engineering.

Yanjiao Jiang, J. Chen, C. Deng, E. Suuronen, Z. Zhong
Published 2014 · Materials Science, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Hydrogels, microgels and nanogels have emerged as versatile and viable platforms for sustained protein release, targeted drug delivery, and tissue engineering due to excellent biocompatibility, a microporous structure with tunable porosity and pore size, and dimensions spanning from human organs, cells to viruses. In the past decade, remarkable advances in hydrogels, microgels and nanogels have been achieved with click chemistry. It is a most promising strategy to prepare gels with varying dimensions owing to its high reactivity, superb selectivity, and mild reaction conditions. In particular, the recent development of copper-free click chemistry such as strain-promoted azide-alkyne cycloaddition, radical mediated thiol-ene chemistry, Diels-Alder reaction, tetrazole-alkene photo-click chemistry, and oxime reaction renders it possible to form hydrogels, microgels and nanogels without the use of potentially toxic catalysts or immunogenic enzymes that are commonly required. Notably, unlike other chemical approaches, click chemistry owing to its unique bioorthogonal feature does not interfere with encapsulated bioactives such as living cells, proteins and drugs and furthermore allows versatile preparation of micropatterned biomimetic hydrogels, functional microgels and nanogels. In this review, recent exciting developments in click hydrogels, microgels and nanogels, as well as their biomedical applications such as controlled protein and drug release, tissue engineering, and regenerative medicine are presented and discussed.
This paper references
10.1073/pnas.1215498110
Hydrogel drug delivery system with predictable and tunable drug release and degradation rates
G. Ashley (2013)
10.1038/nbt818
Repair of bone defects using synthetic mimetics of collagenous extracellular matrices
M. Lutolf (2003)
10.1021/CM300298N
Direct ″Click″ Synthesis of Hybrid Bisphosphonate–Hyaluronic Acid Hydrogel in Aqueous Solution for Biomineralization
X. Yang (2012)
10.1016/j.biomaterials.2012.04.006
Functional performance of human cardiosphere-derived cells delivered in an in situ polymerizable hyaluronan-gelatin hydrogel.
K. Cheng (2012)
10.1021/mz3003775
Strain-Promoted Crosslinking of PEG-based Hydrogels via Copper-Free Cycloaddition.
Jukuan Zheng (2012)
10.1021/la3051115
Ultralow protein adsorbing coatings from clickable PEG nanogel solutions: benefits of attachment under salt-induced phase separation conditions and comparison with PEG/albumin nanogel coatings.
Casey D Donahoe (2013)
10.1021/bm300752j
Cross-linking and degradation of step-growth hydrogels formed by thiol-ene photoclick chemistry.
Han M. Shih (2012)
10.1002/(SICI)1097-4636(199911)47:2<152::AID-JBM5>3.0.CO;2-I
New strategy for chemical modification of hyaluronic acid: preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels.
P. Bulpitt (1999)
10.1021/bm400637s
In situ forming hydrogels via catalyst-free and bioorthogonal "tetrazole-alkene" photo-click chemistry.
Yaping Fan (2013)
10.1016/j.ijpharm.2009.05.051
Influence of dialkyne structure on the properties of new click-gels based on hyaluronic acid.
Gabriella Testa (2009)
10.1016/j.ijpharm.2008.01.057
In situ gelling hydrogels for pharmaceutical and biomedical applications.
Sophie R. Van Tomme (2008)
10.1016/j.biomaterials.2013.02.020
A Diels-Alder modulated approach to control and sustain the release of dexamethasone and induce osteogenic differentiation of human mesenchymal stem cells.
K. C. Koehler (2013)
10.1021/mz300585q
Bioorthogonal Click Chemistry: An Indispensable Tool to Create Multifaceted Cell Culture Scaffolds
Malar A. Azagarsamy (2013)
The in fl uence of matrix properties on growth and morphogenesis of human pancreatic ductal epithelial cells in 3 D
A Raza (2013)
10.1002/ADMA.200304621
Cell-responsive synthetic hydrogels
M. Lutolf (2003)
10.1016/j.biomaterials.2010.06.061
Enhanced proteolytic degradation of molecularly engineered PEG hydrogels in response to MMP-1 and MMP-2.
J. Patterson (2010)
10.1016/J.JCONREL.2004.09.025
Hyaluronic acid hydrogel as Nogo-66 receptor antibody delivery system for the repairing of injured rat brain: in vitro.
W. Tian (2005)
10.1038/NMAT1092
A photolabile hydrogel for guided three-dimensional cell growth and migration
Y. Luo (2004)
10.1038/nmat3101
Spatially controlled simultaneous patterning of multiple growth factors in three-dimensional hydrogels.
R. Wylie (2011)
Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments
C. DeForest (2009)
10.1002/asia.201100411
Cytocompatible poly(ethylene glycol)-co-polycarbonate hydrogels cross-linked by copper-free, strain-promoted click chemistry.
J. Xu (2011)
New approaches in hydrogel synthesis -- Click chemistry: A review
A. Uliniuc (2012)
10.1021/am302690t
Interfacial thiol-ene photoclick reactions for forming multilayer hydrogels.
Han M. Shih (2013)
10.1021/bm100137q
Hydrolytically degradable poly(ethylene glycol) hydrogel scaffolds with tunable degradation and mechanical properties.
S. Zustiak (2010)
Synthetically simple, highly resilient hydrogels. Biomacromolecules 2012;13:584e8
J Cui (2012)
Rapidly in situforming degradable hydrogels from dextran thiols through Michael addition. Biomacromolecules 2007;8:1548e56
C Hiemstra (2007)
10.1039/C0PY00100G
Investigation into thiol-(meth)acrylate Michael addition reactions using amine and phosphine catalysts
Guang-Zhao Li (2010)
10.1002/anie.201101019
Reliable and efficient procedures for the conjugation of biomolecules through Huisgen azide-alkyne cycloadditions.
E. Lallana (2011)
Poly(vinyl alcohol)-based hydrogels formed by click chemistry. Macromolecules 2006;39:1709e18
DA Ossipov (2006)
10.1002/JBM.A.31278
Synthesis and characterization of in situ chitosan-based hydrogel via grafting of carboxyethyl acrylate.
M. Kim (2007)
10.1002/ANIE.200490100
Cover Picture: Efficiency and Fidelity in a Click‐Chemistry Route to Triazole Dendrimers by the Copper(I)‐Catalyzed Ligation of Azides and Alkynes (Angew. Chem. Int. Ed. 30/2004)
P. Wu (2004)
10.1016/J.JCONREL.2007.04.019
Production of heparin-functionalized hydrogels for the development of responsive and controlled growth factor delivery systems.
T. Nie (2007)
10.1002/jbm.a.34107
Student award for outstanding research winner in the Ph.D. category for the 9th World Biomaterials Congress, Chengdu, China, June 1-5, 2012: synthesis and application of photodegradable microspheres for spatiotemporal control of protein delivery.
Mark W. Tibbitt (2012)
10.1016/j.biomaterials.2010.05.064
Cartilage repair using hyaluronan hydrogel-encapsulated human embryonic stem cell-derived chondrogenic cells.
W. Toh (2010)
10.1073/pnas.0737381100
Synthetic matrix metalloproteinase-sensitive hydrogels for the conduction of tissue regeneration: Engineering cell-invasion characteristics
M. Lutolf (2003)
10.1021/bm101446k
Diels-Alder Click cross-linked hyaluronic acid hydrogels for tissue engineering.
Chelsea M Nimmo (2011)
10.1016/J.POLYMER.2005.07.089
Synthesis and characterization of new injectable and degradable dextran-based hydrogels
J. Maia (2005)
10.1021/bm1007986
Functionalization of hyaluronic acid with chemoselective groups via a disulfide-based protection strategy for in situ formation of mechanically stable hydrogels.
D. Ossipov (2010)
10.1016/J.POLYMER.2013.01.001
Preparation and swelling properties of “click” hydrogel from polyaspartamide derivatives using tri-arm PEG and PEG-co-poly(amino urethane) azides as crosslinking agents
N. Huynh (2013)
10.1016/J.PROGPOLYMSCI.2012.04.002
The furan/maleimide Diels–Alder reaction: A versatile click–unclick tool in macromolecular synthesis
A. Gandini (2013)
10.1021/ja902857b
In situ cross-linkable high molecular weight hyaluronan-bisphosphonate conjugate for localized delivery and cell-specific targeting: a hydrogel linked prodrug approach.
Oommen P Varghese (2009)
10.1039/C2PY20826A
Relative reactivity and selectivity of vinyl sulfones and acrylates towards the thiol–Michael addition reaction and polymerization
S. Chatani (2013)
10.1016/j.addr.2008.02.004
Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry.
J. Lutz (2008)
10.1021/MA400543U
Orthogonal Chemoselective Assembly of Hyaluronic Acid Networks and Nanogels for Drug Delivery
D. Ossipov (2013)
10.1021/BM049614C
Recombinant protein-co-PEG networks as cell-adhesive and proteolytically degradable hydrogel matrixes. Part I: Development and physicochemical characteristics.
S. Rizzi (2005)
10.1016/j.actbio.2012.01.028
An in situ cross-linking hybrid hydrogel for controlled release of proteins.
Hila Epstein-Barash (2012)
10.1039/b901979k
Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis.
Charles E. Hoyle (2010)
10.1021/cr200157d
Hydrogels for protein delivery.
T. Vermonden (2012)
10.1016/j.biomaterials.2011.08.083
PEG hydrogels formed by thiol-ene photo-click chemistry and their effect on the formation and recovery of insulin-secreting cell spheroids.
Chien-Chi Lin (2011)
10.1021/bc900087a
Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies.
M. V. van Dijk (2009)
10.1016/j.biomaterials.2008.09.027
DNA delivery from matrix metalloproteinase degradable poly(ethylene glycol) hydrogels to mouse cloned mesenchymal stem cells.
Yuguo Lei (2009)
10.1021/bm9004639
Synthesis by AGET ATRP of degradable nanogel precursors for in situ formation of nanostructured hyaluronic acid hydrogel.
S. Bencherif (2009)
10.1016/j.actbio.2010.12.005
Biological hydrogel synthesized from hyaluronic acid, gelatin and chondroitin sulfate by click chemistry.
X. Hu (2011)
10.1016/S0142-9612(02)00100-X
Glycosaminoglycan hydrogel films as bio-interactive dressings for wound healing.
K. R. Kirker (2002)
10.1016/j.biomaterials.2008.08.018
The effect of immobilized platelet derived growth factor AA on neural stem/progenitor cell differentiation on cell-adhesive hydrogels.
Yukie Aizawa (2008)
10.1021/MA801630N
Development of Thermal and Photochemical Strategies for Thiol−Ene Click Polymer Functionalization
L. Campos (2008)
10.1038/nchem.1174
Cytocompatible Click-based Hydrogels with Dynamically-Tunable Properties Through Orthogonal Photoconjugation and Photocleavage Reactions
C. DeForest (2011)
10.1038/nature02791
Chemical remodelling of cell surfaces in living animals
Jennifer A. Prescher (2004)
10.1016/J.BIOMATERIALS.2006.12.012
Anti-inflammatory function of an in situ cross-linkable conjugate hydrogel of hyaluronic acid and dexamethasone.
Taichi Ito (2007)
10.1039/C3TB20831A
Investigation of the Diels-Alder reaction as a cross-linking mechanism for degradable poly(ethylene glycol) based hydrogels.
S. Kirchhof (2013)
10.1126/science.1214804
Designing Cell-Compatible Hydrogels for Biomedical Applications
D. Seliktar (2012)
10.1016/j.actbio.2011.11.024
Hydrazone self-crosslinking of multiphase elastin-like block copolymer networks.
U. Krishna (2012)
Synthesis and characterization of enzymatically biodegradable PEG and peptidebased hydrogels prepared by click chemistry. Biomacromolecules 2010;11: 1608e14
M van Dijk (2010)
10.1021/bm201802w
Photoinitiated alkyne-azide click and radical cross-linking reactions for the patterning of PEG hydrogels.
Rodney T. Chen (2012)
10.1016/J.BIOMATERIALS.2006.04.043
In situ cross-linkable hyaluronic acid hydrogels prevent post-operative abdominal adhesions in a rabbit model.
Y. Yeo (2006)
10.1002/JBM.A.30831
Synthesis and evaluation of injectable, in situ crosslinkable synthetic extracellular matrices for tissue engineering.
X. Z. Shu (2006)
10.1016/j.biomaterials.2010.07.035
Patterning network structure to spatially control cellular remodeling and stem cell fate within 3-dimensional hydrogels.
Sudhir Khetan (2010)
10.1039/C3BM00166K
Synthetic hydrogel platform for three-dimensional culture of embryonic stem cell-derived motor neurons.
D. McKinnon (2013)
10.1021/bm4000162
Microfluidic synthesis of cell-type-specific artificial extracellular matrix hydrogels.
S. Allazetta (2013)
10.1002/ANIE.200454078
Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes.
P. Wu (2004)
10.1016/j.biomaterials.2011.01.064
The performance of human mesenchymal stem cells encapsulated in cell-degradable polymer-peptide hydrogels.
Sarah E B Anderson (2011)
Synthesis and characterization of new injectable and degradable dextran-based hydrogels. Polymer 2005;46:9604e14
J Maia (2005)
10.1002/CHIN.201003232
Cu(I)-Catalyzed Huisgen Azide—Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry
F. Amblard (2010)
10.1002/marc.201100125
Direct synthesis of biodegradable polysaccharide derivative hydrogels through aqueous Diels-Alder chemistry.
H. Tan (2011)
10.1039/c2ib20212c
Responsive culture platform to examine the influence of microenvironmental geometry on cell function in 3D.
April M Kloxin (2012)
10.1002/jbm.a.33199
Novel injectable biodegradable glycol chitosan-based hydrogels crosslinked by Michael-type addition reaction with oligo(acryloyl carbonate)-b-poly(ethylene glycol)-b-oligo(acryloyl carbonate) copolymers.
Yuexin Yu (2011)
10.1088/1748-6041/7/2/024106
Degradable, click poly(vinyl alcohol) hydrogels: characterization of degradation and cellular compatibility.
M. Alves (2012)
10.1021/bm2013982
Injectable, mixed natural-synthetic polymer hydrogels with modular properties.
M. Patenaude (2012)
10.1016/j.biomaterials.2010.10.020
Hydrogels with time-dependent material properties enhance cardiomyocyte differentiation in vitro.
J. Young (2011)
10.1021/MA062468D
Novel in situ forming, degradable dextran hydrogels by Michael addition chemistry : Synthesis, rheology, and degradation
C. Hiemstra (2007)
10.1002/POLA.24015
Synthesis of thermosensitive guar‐based hydrogels with tunable physico‐chemical properties by click chemistry
M. Tizzotti (2010)
10.1021/cr0783479
Cu-catalyzed azide-alkyne cycloaddition.
M. Meldal (2008)
10.1021/JA072113P
Rapidly in situ forming biodegradable robust hydrogels by combining stereocomplexation and photopolymerization.
C. Hiemstra (2007)
10.1002/adma.201103574
Maleimide cross-linked bioactive PEG hydrogel exhibits improved reaction kinetics and cross-linking for cell encapsulation and in situ delivery.
Edward A. Phelps (2012)
10.1016/j.actbio.2013.01.026
Three-dimensional hMSC motility within peptide-functionalized PEG-based hydrogels of varying adhesivity and crosslinking density.
K. A. Kyburz (2013)
10.1038/nmat2784
Nanogel antigenic protein-delivery system for adjuvant-free intranasal vaccines.
T. Nochi (2010)
10.1038/nature08602
Designing materials to direct stem-cell fate
M. Lutolf (2009)
10.1016/j.biomaterials.2009.08.031
Characterization of valvular interstitial cell function in three dimensional matrix metalloproteinase degradable PEG hydrogels.
J. Benton (2009)
10.1002/adma.201202881
Modular 'click-in-emulsion' bone-targeted nanogels.
D. Heller (2013)
10.1021/cm101391y
Peptide-Functionalized Click Hydrogels with Independently Tunable Mechanics and Chemical Functionality for 3D Cell Culture
C. DeForest (2010)
10.1002/ADFM.201201698
Smart Design of Stable Extracellular Matrix Mimetic Hydrogel: Synthesis, Characterization, and In Vitro and In Vivo Evaluation for Tissue Engineering
Oommen P. Oommen (2013)
10.1021/BM061191M
Rapidly in situ-forming degradable hydrogels from dextran thiols through Michael addition.
C. Hiemstra (2007)
10.1021/MA300593G
Mechanical Properties of End-Linked PEG/PDMS Hydrogels
J. Cui (2012)
10.1016/J.PROGPOLYMSCI.2006.03.001
Michael addition reactions in macromolecular design for emerging technologies
B. D. Mather (2006)
10.1021/MA052545P
Poly(vinyl alcohol)-Based Hydrogels Formed by “Click Chemistry”
D. Ossipov (2006)
Recombinant protein-co-PEG networks as cell-adhesive and proteolytically degradable hydrogel matrixes. Part 1: development and physicochemical characteristics. Biomacromolecules 2005;6:1226e38
SC Rizzi (2005)
Micro fl uidic Synthesis of Cell-Type-Speci fi c Arti fi cial Extracellular Matrix Hydrogels
S. Allazetta (2013)
In situ crosslinkable hyaluronic acid hydrogels prevent post-operative abdominal adhesions in a rabbit model. Biomaterials 2006;27:4698e705
Y Yeo (2006)
Preparation and swelling properties of “click” hydrogel from polyaspartamide derivatives using tri-arm PEG and PEG-co-poly(amino urethane) azides as crosslinking agents. Polymer 2013;54:1341e9
Huynh N-T (2013)
10.1016/j.biomaterials.2008.11.023
Biodegradable poly(ethylene glycol)-peptide hydrogels with well-defined structure and properties for cell delivery.
Shao Qiong Liu (2009)
10.1016/j.actbio.2008.12.004
Production of heparin-containing hydrogels for modulating cell responses.
T. Nie (2009)
10.1021/bm3012924
Hydrophilic and amphiphilic polyethylene glycol-based hydrogels with tunable degradability prepared by "click" chemistry.
V. Truong (2012)
AeschlimannD.New strategy for chemicalmodification of hyaluronic acid: preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels
P Bulpitt (1999)
10.1021/CM071158M
Three-dimensional Chemical Patterning of Transparent Hydrogels
J. Wosnick (2008)
10.1002/POLA.22857
“Click” chemistry for in situ formation of thermoresponsive P(NIPAAm‐co‐HEMA)‐based hydrogels
Xiao-Ding Xu (2008)
10.1002/CHIN.200925260
Thermoresponsive Microgel-Based Materials
L. Lyon (2009)
10.1016/J.BIOMATERIALS.2003.08.014
In situ crosslinkable hyaluronan hydrogels for tissue engineering.
Xiao Zheng Shu (2004)
10.1016/j.jconrel.2012.08.002
Cell-mediated delivery of glucocorticoids from thiol-ene hydrogels.
C. Yang (2012)
10.1002/anie.201308005
A microgel construction kit for bioorthogonal encapsulation and pH-controlled release of living cells.
D. Steinhilber (2013)
10.1021/bm300671s
Thiol–Ene Photopolymerizations Provide a Facile Method To Encapsulate Proteins and Maintain Their Bioactivity
Joshua D. McCall (2012)
10.1016/J.JCONREL.2007.06.011
Release of model proteins and basic fibroblast growth factor from in situ forming degradable dextran hydrogels.
C. Hiemstra (2007)
10.1021/BM0700800
Novel hydrogels via click chemistry: synthesis and potential biomedical applications.
V. Crescenzi (2007)
Synthetically tractable click hydrogels for three-dimensional cell culture formed using tetrazinenorbornene chemistry. Biomacromolecules 2013;14:949e53
DL Alge (2013)
10.1039/b715522k
Thermoresponsive microgel-based materials.
L. A. Lyon (2009)
10.1016/j.actbio.2013.06.021
Thiol-ene Michael-type formation of gelatin/poly(ethylene glycol) biomatrices for three-dimensional mesenchymal stromal/stem cell administration to cutaneous wounds.
K. Xu (2013)
10.1021/BM049607O
Network formation and degradation behavior of hydrogels formed by Michael-type addition reactions.
A. Metters (2005)
10.1016/j.biomaterials.2012.10.008
Fully defined in situ cross-linkable alginate and hyaluronic acid hydrogels for myocardial tissue engineering.
J. Dahlmann (2013)
10.1016/j.biomaterials.2009.07.043
Poly(ethylene glycol) hydrogels formed by thiol-ene photopolymerization for enzyme-responsive protein delivery.
A. A. Aimetti (2009)
10.1089/TEN.2006.12.601
Fibronectin functional domains coupled to hyaluronan stimulate adult human dermal fibroblast responses critical for wound healing.
K. Ghosh (2006)
10.1021/BM025744E
Synthesis and physicochemical characterization of end-linked poly(ethylene glycol)-co-peptide hydrogels formed by Michael-type addition.
M. Lutolf (2003)
10.1002/bit.22911
Characterization of protein release from hydrolytically degradable poly(ethylene glycol) hydrogels
S. Zustiak (2011)
10.1038/nchem.980
Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction.
Brian J. Adzima (2011)
10.1016/j.biomaterials.2010.08.106
An injectable thiol-acrylate poly(ethylene glycol) hydrogel for sustained release of methylprednisolone sodium succinate.
Christopher D. Pritchard (2011)
10.1039/B820385G
Sequential crosslinking to control cellular spreading in 3-dimensional hydrogels
Sudhir Khetan (2009)
10.1016/S0168-3659(01)00398-4
Protein delivery from materials formed by self-selective conjugate addition reactions.
D. Elbert (2001)
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
V. Rostovtsev (2002)
10.1021/bm7012636
Three-dimensional biochemical patterning of click-based composite hydrogels via thiolene photopolymerization.
B. D. Polizzotti (2008)
10.1002/adma.201001855
Endothelial cell guidance in 3D patterned scaffolds.
Yukie Aizawa (2010)
10.1016/J.CARBPOL.2009.01.023
Synthesis of thermosensitive P(NIPAAm-co-HEMA)/cellulose hydrogels via “click” chemistry
J. Zhang (2009)
Synthesis and physicochemical characterization of end-linked poly(ethylene glycol)-co-peptide hydrogels formed by Michaeltype addition. Biomacromolecules 2003;4:713e22
MP Lutolf (2003)
10.1021/bm301034a
Biointerface properties of core-shell poly(vinyl alcohol)-hyaluronic acid microgels based on chemoselective chemistry.
S. Kupal (2012)
10.1039/b809167f
Metal free thiol-maleimide 'Click' reaction as a mild functionalisation strategy for degradable polymers.
Ryan J. Pounder (2008)
10.1021/bm300015s
Synthetically simple, highly resilient hydrogels.
J. Cui (2012)
10.1039/C2PY20576A
Reversible maleimide-thiol adducts yield glutathione-sensitive poly(ethylene glycol)-heparin hydrogels.
Aaron D Baldwin (2013)
10.1021/bm4009606
In situ cross-linkable hydrogel of hyaluronan produced via copper-free click chemistry.
A. Takahashi (2013)
10.1021/la305000w
Hyaluronic acid click hydrogels emulate the extracellular matrix.
S. Owen (2013)
10.1021/BC015519E
Systematic modulation of Michael-type reactivity of thiols through the use of charged amino acids.
M. Lutolf (2001)
10.1016/J.BIOMATERIALS.2003.12.012
Prolongation of sciatic nerve blockade by in situ cross-linked hyaluronic acid.
X. Jia (2004)
10.1039/B603438A
Synthesis of well-defined hydrogel networks using click chemistry.
M. Malkoch (2006)
10.1021/bm301346e
Biocompatible hydrogels by oxime Click chemistry.
G. Grover (2012)
10.1016/j.actbio.2012.05.009
Small peptide functionalized thiol-ene hydrogels as culture substrates for understanding valvular interstitial cell activation and de novo tissue deposition.
Sarah T Gould (2012)
10.1016/J.PROGPOLYMSCI.2009.08.001
Biopolymer-based microgels/nanogels for drug delivery applications
J. Oh (2009)
10.1016/J.CARBPOL.2011.04.031
A “click-chemistry” approach to cellulose-based hydrogels
A. Koschella (2011)
10.1002/marc.201200605
Visible-light-mediated thiol-ene hydrogelation using eosin-Y as the only photoinitiator.
Han M. Shih (2013)
10.1016/j.actbio.2009.12.024
Synthesis and characterization of hyaluronic acid-poly(ethylene glycol) hydrogels via Michael addition: An injectable biomaterial for cartilage repair.
R. Jin (2010)
10.1002/CHIN.200728264
′Click′ Chemistry in Polymer and Materials Science
W. Binder (2007)
10.1001/archfacial.2010.37
Repair of a calvarial defect with biofactor and stem cell-embedded polyethylene glycol scaffold.
A. Terella (2010)
10.1002/marc.201200337
Preparation of fluorescent organometallic porphyrin complex nanogels of controlled molecular structure via reverse-emulsion click chemistry.
Guodong Fu (2012)
10.1016/j.biomaterials.2013.03.086
The influence of matrix properties on growth and morphogenesis of human pancreatic ductal epithelial cells in 3D.
A. Raza (2013)
10.1016/j.jconrel.2008.01.005
In situ gelling stimuli-sensitive block copolymer hydrogels for drug delivery.
Chaoliang He (2008)
10.1007/s11095-012-0683-y
Click Chemistry with Polymers, Dendrimers, and Hydrogels for Drug Delivery
E. Lallana (2012)
10.1126/science.1155106
In Vivo Imaging of Membrane-Associated Glycans in Developing Zebrafish
Scott T Laughlin (2008)
10.1016/j.jconrel.2012.12.008
Surfactant free preparation of biodegradable dendritic polyglycerol nanogels by inverse nanoprecipitation for encapsulation and release of pharmaceutical biomacromolecules.
D. Steinhilber (2013)
10.1016/J.PROGPOLYMSCI.2008.01.002
The development of microgels/nanogels for drug delivery applications
J. Oh (2008)
10.1021/BM0701189
Formation of a novel heparin-based hydrogel in the presence of heparin-binding biomolecules.
Giyoong Tae (2007)
10.1016/J.CARBPOL.2011.02.014
Detailed characterization of an injectable hyaluronic acid-polyaspartylhydrazide hydrogel for protein delivery
R. Zhang (2011)
10.1021/bm1002637
Synthesis and characterization of enzymatically biodegradable PEG and peptide-based hydrogels prepared by click chemistry.
M. V. van Dijk (2010)
10.1021/ja300460p
Controlled synthesis of cell-laden microgels by radical-free gelation in droplet microfluidics.
Torsten Rossow (2012)
10.1021/bm301789d
Diels-Alder mediated controlled release from a poly(ethylene glycol) based hydrogel.
K. C. Koehler (2013)
10.1016/j.carbpol.2012.07.054
Reductive alkylation of hyaluronic acid for the synthesis of biocompatible hydrogels by click chemistry.
Gloria Huerta-Ángeles (2012)
10.1002/marc.200800671
Modular Synthesis of Thermosensitive P(NIPAAm-co-HEMA)/β-CD Based Hydrogels via Click Chemistry.
Xiao-Ding Xu (2009)
10.1039/b713009k
Injectable hydrogels as unique biomedical materials.
Lin Yu (2008)
10.1021/BM060504A
Recombinant protein-co-PEG networks as cell-adhesive and proteolytically degradable hydrogel matrixes. Part II: biofunctional characteristics.
S. Rizzi (2006)
10.1002/anie.201106463
Photoreversible Patterning of Biomolecules within Click-Based Hydrogels**
C. DeForest (2012)
Poly(ethylene glycol) hydrogels formed by thiol-ene photopolymerization for enzyme-responsive protein delivery. Biomaterials 2009;30:6048e54
AA Aimetti (2009)
10.1021/BM061059M
Rapid cross-linking of elastin-like polypeptides with (hydroxymethyl)phosphines in aqueous solution.
D. W. Lim (2007)
10.1021/bm100514p
Photopolymerized thermosensitive poly(HPMAlactate)-PEG-based hydrogels: effect of network design on mechanical properties, degradation, and release behavior.
R. Censi (2010)
10.1016/j.jconrel.2011.02.003
Bone reservoir: Injectable hyaluronic acid hydrogel for minimal invasive bone augmentation.
E. Martínez-Sanz (2011)
10.1016/J.POLYMER.2009.04.032
Thermosensitive hydrogels synthesized by fast Diels–Alder reaction in water
Hong-liang Wei (2009)
10.1002/adma.200901808
A Versatile Synthetic Extracellular Matrix Mimic via Thiol-Norbornene Photopolymerization.
B. Fairbanks (2009)
10.1021/bm4000508
Synthetically Tractable Click Hydrogels for Three-Dimensional Cell Culture Formed Using Tetrazine–Norbornene Chemistry
D. Alge (2013)
10.1016/J.POLYMER.2008.01.027
HYDROGELS IN DRUG DELIVERY: PROGRESS AND CHALLENGES
T. Hoare (2008)
10.1021/bc200281k
Regenerative biomaterials that "click": simple, aqueous-based protocols for hydrogel synthesis, surface immobilization, and 3D patterning.
Chelsea M Nimmo (2011)
10.1039/c0cc03055d
Modular approach to functional hyaluronic acid hydrogels using orthogonal chemical reactions.
D. Ossipov (2010)
10.1016/S0142-9612(02)00227-2
A hydrogel prepared by in situ cross-linking of a thiol-containing poly(ethylene glycol)-based copolymer: a new biomaterial for protein drug delivery.
B. Qiu (2003)
10.1016/j.jcis.2012.07.096
Tuning drug release from smart microgel-hydrogel composites via cross-linking.
Daryl N. Sivakumaran (2013)
10.1021/bm2015834
Development of a hybrid dextrin hydrogel encapsulating dextrin nanogel as protein delivery system.
Maria Molinos (2012)
10.1016/S0142-9612(00)00116-2
Novel injectable neutral solutions of chitosan form biodegradable gels in situ.
A. Chenite (2000)
10.1016/J.BIOMATERIALS.2007.02.032
Enzyme-mediated fast in situ formation of hydrogels from dextran-tyramine conjugates.
R. Jin (2007)
10.1021/JO011148J
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
C. W. Tornøe (2002)
Photoinitiated alkyneeazide click and radical cross-linking reactions for the patterning of PEG hydrogels. Biomacromolecules 2012;13:889e95
RT Chen (2012)
10.1002/POLA.20366
Thiol–enes: Chemistry of the past with promise for the future
C. Hoyle (2004)



This paper is referenced by
10.3390/pharmaceutics11080407
Strategies for Hyaluronic Acid-Based Hydrogel Design in Drug Delivery
S. Trombino (2019)
10.1016/J.EURPOLYMJ.2015.08.032
The past, present and future of hydrogels
T. Vermonden (2015)
10.1002/adhm.201500757
Click-Crosslinked Injectable Gelatin Hydrogels.
Sandeep T. Koshy (2016)
10.3390/gels4030067
Concepts for Developing Physical Gels of Chitosan and of Chitosan Derivatives
Pasquale Sacco (2018)
10.1002/chem.201904446
Cell-Encapsulating Hydrogel Puzzle: Polyrotaxane-Based Self-Healing Hydrogels.
Ik Sung Cho (2019)
10.1016/j.biomaterials.2017.09.004
AIEgens for biological process monitoring and disease theranostics.
X. Gu (2017)
10.1039/C6TB02019D
Functional biomedical hydrogels for in vivo imaging.
Kewen Lei (2016)
10.1039/C7NH00062F
Fully degradable protein nanocarriers by orthogonal photoclick tetrazole-ene chemistry for the encapsulation and release.
Keti Piradashvili (2017)
10.1021/acs.molpharmaceut.7b00067
Bio-Orthogonal Cross-Linking Chemistry Enables In Situ Protein Encapsulation and Provides Sustained Release from Hyaluronic Acid Based Hydrogels.
A. Famili (2017)
10.1039/c8sm01510d
Do the properties of gels constructed by interlinking triply-responsive microgels follow from those of the building blocks?
Dongdong Lu (2019)
10.1021/acsami.6b05775
Redox-Sensitive and Intrinsically Fluorescent Photoclick Hyaluronic Acid Nanogels for Traceable and Targeted Delivery of Cytochrome c to Breast Tumor in Mice.
S. Li (2016)
10.1007/978-3-319-76573-0_41-1
Cellulose-Based Hydrogels in Topical Drug Delivery : A Challenge in Medical Devices
A. Ribeiro (2018)
10.1038/s41598-020-63228-9
Poly(N-isopropylacrylamide) based thin microgel films for use in cell culture applications
I. Sanzari (2020)
10.1002/ADFM.201800011
pH‐Responsive, Light‐Triggered on‐Demand Antibiotic Release from Functional Metal–Organic Framework for Bacterial Infection Combination Therapy
Zhiyong Song (2018)
Development of orthogonally crosslinked thiol-ene hydrogels for encapsulation of pancreatic beta-cells
H. Shih (2016)
10.1021/MA501386V
“Click”-Inspired Chemistry in Macromolecular Science: Matching Recent Progress and User Expectations
Pieter Espeel (2015)
10.1016/j.jconrel.2019.10.048
Cationic Synthetic Long Peptides-Loaded Nanogels: An Efficient Therapeutic Vaccine formulation for induction of T-cell Responses.
Neda Kordalivand (2019)
10.1016/j.msec.2020.111357
Novel multi-responsive and sugarcane bagasse cellulose-based nanogels for controllable release of doxorubicin hydrochloride
Y. Pan (2021)
10.1039/c9cc09473c
Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications.
D. A. Bilodeau (2020)
SPECIFIC DNA SEQUENCE RESPONISIVE DNA CROSSLINKED HYDROGEL AND ITS APPLICATIONS
Qi Zhang Huang (2017)
10.1039/C7TB00721C
Three-Dimensional Hyaluronic Acid Hydrogel-Based Models for In Vitro Human iPSC-Derived NPC Culture and Differentiation.
S. Wu (2017)
10.1007/978-3-319-61288-1_4
Innovative Systems from Clickable Biopolymer-Based Hydrogels for Drug Delivery
C. García-Astrain (2017)
10.1002/mabi.201900099
Rational Design and Development of Anisotropic and Mechanically Strong Gelatin-Based Stress Relaxing Hydrogels for Osteogenic/Chondrogenic Differentiation.
K. Dey (2019)
10.20381/RUOR-24402
Collagen Hydrogels for Regenerative Medicine
Justina Pupkaite (2020)
10.1016/J.POLYMER.2018.07.020
Mechanical response of double-network gels with dynamic bonds under multi-cycle deformation
A. Drozdov (2018)
10.1155/2019/6508094
Biological Influence of Nonswelling Microgels on Cartilage Induction of Mouse Adipose-Derived Stem Cells
Z. Liu (2019)
10.1109/JMEMS.2015.2477217
3-D Non-UV Digital Printing of Hydrogel Microstructures by Optically Controlled Digital Electropolymerization
N. Liu (2015)
10.1016/j.ijbiomac.2015.11.050
Fabrication of PEG-carboxymethylcellulose hydrogel by thiol-norbornene photo-click chemistry.
Sora Lee (2016)
10.1016/J.REACTFUNCTPOLYM.2017.12.019
Soft hydrazone crosslinked hyaluronan- and alginate-based hydrogels as 3D supportive matrices for human pluripotent stem cell-derived neuronal cells
Jennika Karvinen (2018)
10.1002/mabi.201700127
In Vitro Evaluation of Anti-Aggregation and Degradation Behavior of PEGylated Polymeric Nanogels under In Vivo Like Conditions.
Y. Chen (2018)
10.1021/ACSBIOMATERIALS.7B00397
Injectable and Degradable Poly(Oligoethylene glycol methacrylate) Hydrogels with Tunable Charge Densities as Adhesive Peptide-Free Cell Scaffolds
Emilia Bakaic (2017)
10.1080/00914037.2020.1716225
Tailoring size and release kinetics of κ/ι-hybrid carrageenan microgels via a surfactant-assisted technique
S. Rodríguez (2020)
See more
Semantic Scholar Logo Some data provided by SemanticScholar