A mild, large-scale synthesis of 1,3-cyclooctanedione: expanding access to difluorinated cyclooctyne for copper-free click chemistry

Sims, Evan A.; DeForest, Cole A.; Anseth, Kristi S.

doi:10.1016/j.tetlet.2011.02.029

Cited by 11 publications

(10 citation statements)

References 31 publications

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“…DIFO3 19 , 39 (121 mg, 0.6 mmol, See Supplementary Fig. S12 ) and 2-(1H-7-Azabenzotriazol-1-yl)--1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium (HATU, 225 mg, 0.6 mmol, Anaspec) were dissolved in minimal dimethylformamide (DMF, 5 mL) with N , N -diisopropylethylamine (DIEA, 210μL, 1.2 mmol) and reacted for 5 min at RT.…”

Section: Methodsmentioning

confidence: 99%

Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions

2011

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To provide insight as to how cells receive information from their external surroundings, synthetic hydrogels have emerged as systems for assaying cell function in well-defined microenvironments where single cues can be introduced and subsequent effects individually elucidated. However, as the field seeks to answer more complex biological questions, advanced material systems are needed that allow dynamic alteration of the 3D cellular environment with orthogonal reactions that enable multiple levels of control of biochemical and biomechanical signals. Here, we sought to synthesize one such 3D culture system using cytocompatible and wavelength-specific photochemical reactions to create hydrogels that allow orthogonal and dynamic control of the material properties through independent spatiotemporally-regulated photocleavage of crosslinks and photoconjugation of pendant functionalities. Results demonstrate the versatile nature of the chemistry to create programmable niches to study and direct cell function by modifying the local hydrogel environment.

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Section: Methodsmentioning

confidence: 99%

Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions

2011

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“…18 In contrast, the second-generation DIFO molecule that we previously used (i.e., DIFO3) was synthesized in 12–13 steps and obtained in approximately 8% yield. 19,20 …”

Section: Introductionmentioning

confidence: 99%

Synthetically Tractable Click Hydrogels for Three-Dimensional Cell Culture Formed Using Tetrazine–Norbornene Chemistry

et al. 2013

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The implementation of bio-orthogonal click chemistries is a topic of growing importance in the field of biomaterials, as it is enabling the development of increasingly complex hydrogel materials capable of providing dynamic, cell-instructive microenvironments. Here, we introduce the tetrazine–norbornene inverse electron demand Diels–Alder reaction as a new cross-linking chemistry for the formation of cell laden hydrogels. The fast reaction rate and irreversible nature of this click reaction allowed for hydrogel formation within minutes when a multifunctional PEG-tetrazine macromer was reacted with a dinorbornene peptide. In addition, the cytocompatibility of the polymerization led to high postencapsulation viability of human mesenchymal stem cells, and the specificity of the tetrazine–norbornene reaction was exploited for sequential modification of the network via thiol–ene photochemistry. These advantages, combined with the synthetic accessibility of the tetrazine molecule compared to other bio-orthogonal click reagents, make this cross-linking chemistry an interesting and powerful new tool for the development of cell-instructive hydrogels for tissue engineering applications.

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“…The hydrogel was formed by the copper-free, strain-promoted, azide–alkyne cyclooaddition (SPAAC) click reaction between poly(ethylene glycol) (PEG), tetracyclooctyne 17 , 18 ( 2 ), and bis(azido), allyloxycarbonyl (alloc)-protected polypeptide N 3 -RGK(alloc)GRK-N 3 ( 3 ) in an aqueous medium (Figure 1 a ). 7 , 11 , 19 The resulting idealized SPAAC-based network is homogenously populated with alloc functionalities that contain photoreactive alkenes.…”

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Photoreversible Patterning of Biomolecules within Click‐Based Hydrogels

2011

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A mild, large-scale synthesis of 1,3-cyclooctanedione: expanding access to difluorinated cyclooctyne for copper-free click chemistry

Cited by 11 publications

References 31 publications

Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions

Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions

Synthetically Tractable Click Hydrogels for Three-Dimensional Cell Culture Formed Using Tetrazine–Norbornene Chemistry

Photoreversible Patterning of Biomolecules within Click‐Based Hydrogels

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