Bioorthogonal Click Chemistry: An Indispensable Tool to Create Multifaceted Cell Culture Scaffolds

Over the past decade, bioorthogonal click chemistry has led the field of biomaterial science into a new era of diversity and complexity by its extremely selective, versatile, and biocompatible nature. In this viewpoint, we seek to emphasize recent endeavors of exploiting this versatile chemistry toward the development of poly(ethylene glycol) hydrogels as cell culture scaffolds. In these cell-laden materials, the orthogonality of these reactions has played an effective role in allowing the creation of diverse biochemical patterns in complex biological environments that provide new found opportunities for researchers to delineate and control cellular phenotypes more precisely than ever.

[1]  R. Marchant,et al.  Design properties of hydrogel tissue-engineering scaffolds , 2011, Expert review of medical devices.

[2]  K. Anseth,et al.  Thiol–Ene Photopolymerizations Provide a Facile Method To Encapsulate Proteins and Maintain Their Bioactivity , 2012, Biomacromolecules.

[3]  Krishnendu Roy,et al.  Biomimetic three-dimensional cultures significantly increase hematopoietic differentiation efficacy of embryonic stem cells. , 2005, Tissue engineering.

[4]  C. Bertozzi,et al.  From Mechanism to Mouse: A Tale of Two Bioorthogonal Reactions , 2011, Accounts of chemical research.

[5]  Johnathan N. Brantley,et al.  Polymer Mechanochemistry: Force Enabled Transformations. , 2012, ACS macro letters.

[6]  Johnathan N. Brantley,et al.  Unclicking the Click: Mechanically Facilitated 1,3-Dipolar Cycloreversions , 2011, Science.

[7]  K. Anseth,et al.  Sequential Click Reactions for Synthesizing and Patterning 3D Cell Microenvironments , 2009, Nature materials.

[8]  Craig J. Hawker,et al.  A versatile approach to high-throughput microarrays using thiol-ene chemistry , 2010 .

[9]  Chien-Chi Lin,et al.  PEG hydrogels formed by thiol-ene photo-click chemistry and their effect on the formation and recovery of insulin-secreting cell spheroids. , 2011, Biomaterials.

[10]  M. G. Finn,et al.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions. , 2001, Angewandte Chemie.

[11]  Carolyn R. Bertozzi,et al.  Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry , 2008, Journal of the American Chemical Society.

[12]  A. Khademhosseini,et al.  Hydrogels in Biology and Medicine: From Molecular Principles to Bionanotechnology , 2006 .

[13]  A. Metters,et al.  Synthetic matrix metalloproteinase-sensitive hydrogels for the conduction of tissue regeneration: Engineering cell-invasion characteristics , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[14]  H. Kolb,et al.  The growing impact of click chemistry on drug discovery. , 2003, Drug discovery today.

[15]  Kristi S. Anseth,et al.  Photodegradable Hydrogels for Dynamic Tuning of Physical and Chemical Properties , 2009, Science.

[16]  M. Théry,et al.  Micropatterning as a tool to decipher cell morphogenesis and functions , 2010, Journal of Cell Science.

[17]  J. Hubbell,et al.  Molecularly engineered PEG hydrogels: a novel model system for proteolytically mediated cell migration. , 2005, Biophysical journal.

[18]  J. Moses,et al.  The growing applications of click chemistry. , 2007, Chemical Society reviews.

[19]  J. Hubbell,et al.  Synthesis and physicochemical characterization of end-linked poly(ethylene glycol)-co-peptide hydrogels formed by Michael-type addition. , 2003, Biomacromolecules.

[20]  R Y Tsien,et al.  Specific covalent labeling of recombinant protein molecules inside live cells. , 1998, Science.

[21]  Michael T. Taylor,et al.  Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans-cyclooctenes. , 2012, Journal of the American Chemical Society.

[22]  Carolyn R Bertozzi,et al.  Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. , 2009, Angewandte Chemie.

[23]  Kristi S Anseth,et al.  Mechanical Properties of Cellularly Responsive Hydrogels and Their Experimental Determination , 2010, Advanced materials.

[24]  Julie Glowacki,et al.  Collagen scaffolds for tissue engineering. , 2008, Biopolymers.

[25]  R. Misra,et al.  Biomaterials , 2008 .

[26]  C. Hawker,et al.  "Clicking" polymers or just efficient linking: what is the difference? , 2011, Angewandte Chemie.

[27]  Junmin Zhu,et al.  Bioactive modification of poly(ethylene glycol) hydrogels for tissue engineering. , 2010, Biomaterials.

[28]  M. Bissell,et al.  Interaction with basement membrane serves to rapidly distinguish growth and differentiation pattern of normal and malignant human breast epithelial cells. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[29]  Kristi S. Anseth,et al.  Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction. , 2011, Nature chemistry.

[30]  C. Bowman,et al.  Thiol-yne click chemistry: A powerful and versatile methodology for materials synthesis , 2010 .

[31]  M. Shoichet,et al.  Regenerative biomaterials that "click": simple, aqueous-based protocols for hydrogel synthesis, surface immobilization, and 3D patterning. , 2011, Bioconjugate chemistry.

[32]  A. Dondoni.  The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry. , 2008, Angewandte Chemie.

[33]  Achim Goepferich,et al.  Rational design of hydrogels for tissue engineering: impact of physical factors on cell behavior. , 2007, Biomaterials.

[34]  Cindi M Morshead,et al.  Spatially controlled simultaneous patterning of multiple growth factors in three-dimensional hydrogels. , 2011, Nature materials.

[35]  M. Shoichet,et al.  Diels-Alder Click cross-linked hyaluronic acid hydrogels for tissue engineering. , 2011, Biomacromolecules.

[36]  Kristi S Anseth,et al.  Macromolecular Monomers for the Synthesis of Hydrogel Niches and Their Application in Cell Encapsulation and Tissue Engineering. , 2008, Progress in polymer science.

[37]  R. Weissleder,et al.  Tetrazine-based cycloadditions: application to pretargeted live cell imaging. , 2008, Bioconjugate chemistry.

[38]  Jennifer L. West,et al.  Three‐Dimensional Biochemical and Biomechanical Patterning of Hydrogels for Guiding Cell Behavior , 2006 .

[39]  Jay C. Sy,et al.  Maleimide Cross‐Linked Bioactive PEG Hydrogel Exhibits Improved Reaction Kinetics and Cross‐Linking for Cell Encapsulation and In Situ Delivery , 2012, Advanced materials.

[40]  J. Snyder,et al.  Ultrasound-promoted Diels-Alder reactions: syntheses of tanshinone IIA, nortanshinone, and (.+-.)-tanshindiol B , 1989 .

[41]  Mark W. Tibbitt,et al.  Hydrogels as extracellular matrix mimics for 3D cell culture. , 2009, Biotechnology and bioengineering.

[42]  Timothy E. Long,et al.  Michael addition reactions in macromolecular design for emerging technologies , 2006 .

[43]  L. Shea,et al.  Hydrogel network design using multifunctional macromers to coordinate tissue maturation in ovarian follicle culture. , 2011, Biomaterials.

[44]  Carolyn R. Bertozzi,et al.  Copper-free click chemistry for dynamic in vivo imaging , 2007, Proceedings of the National Academy of Sciences.

[45]  C. Bowman,et al.  Thiol−Yne Photopolymerizations: Novel Mechanism, Kinetics, and Step-Growth Formation of Highly Cross-Linked Networks , 2008, Macromolecules.

[46]  Jennifer A. Prescher,et al.  A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. , 2004, Journal of the American Chemical Society.

[47]  J. Hubbell,et al.  Protein delivery from materials formed by self-selective conjugate addition reactions. , 2001, Journal of controlled release : official journal of the Controlled Release Society.

[48]  Beat Ernst,et al.  Drug discovery today. , 2003, Current topics in medicinal chemistry.

[49]  Krzysztof Matyjaszewski,et al.  Marrying click chemistry with polymerization: expanding the scope of polymeric materials. , 2010, Chemical Society reviews.

[50]  Ralph Müller,et al.  Synthetic extracellular matrices for in situ tissue engineering , 2004, Biotechnology and bioengineering.

[51]  J C M van Hest,et al.  Elastin as a biomaterial for tissue engineering. , 2007, Biomaterials.

[52]  Kristi S. Anseth,et al.  Peptide-Functionalized Click Hydrogels with Independently Tunable Mechanics and Chemical Functionality for 3D Cell Culture , 2010, Chemistry of materials : a publication of the American Chemical Society.

[53]  Kristi S Anseth,et al.  Advances in bioactive hydrogels to probe and direct cell fate. , 2012, Annual review of chemical and biomolecular engineering.

[54]  Jason A Burdick,et al.  Patterning network structure to spatially control cellular remodeling and stem cell fate within 3-dimensional hydrogels. , 2010, Biomaterials.

[55]  宁北芳,et al.  疟原虫var基因转换速率变化导致抗原变异[英]／Paul H, Robert P, Christodoulou Z, et al//Proc Natl Acad Sci U S A , 2005 .

[56]  M. Best,et al.  Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules. , 2009, Biochemistry.

[57]  A James Link,et al.  Non-canonical amino acids in protein engineering. , 2003, Current opinion in biotechnology.

[58]  Joseph M. Fox,et al.  Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity. , 2008, Journal of the American Chemical Society.

[59]  Y. Bae,et al.  Thermosensitive sol-gel reversible hydrogels. , 2002, Advanced drug delivery reviews.

[60]  K. Kiick,et al.  Tunable degradation of maleimide-thiol adducts in reducing environments. , 2011, Bioconjugate chemistry.

[61]  J. Vacanti,et al.  Tissue engineering : Frontiers in biotechnology , 1993 .

[62]  Carolyn R Bertozzi,et al.  Cu-free click cycloaddition reactions in chemical biology. , 2010, Chemical Society reviews.

[63]  Kristi S. Anseth,et al.  A Versatile Synthetic Extracellular Matrix Mimic via Thiol‐Norbornene Photopolymerization , 2009, Advanced materials.

[64]  K. Anseth,et al.  Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol-ene/thiol-yne photoreactions. , 2010, Chemical communications.

[65]  D. Mooney,et al.  Hydrogels for tissue engineering. , 2001, Chemical Reviews.

[66]  C. Tanford.  Macromolecules , 1994, Nature.