Inverse Electron-Demand Diels–Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles

Agramunt, Jordi; Ginesi, Rebecca E; Pedroso, Enrique; Grandas, Anna

doi:10.1021/acs.joc.0c00583

Cited by 14 publications

(5 citation statements)

References 33 publications

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“…CI is prepared following a previously reported procedure 47 with minor modifications. To a solution of 4-(aminomethyl)benzonitrile hydrochloride (10.00 g, 59.3 mmol) in dichloromethane (250 mL), triethylamine (20.7 mL, 148.5 mmol) and Boc 2 O (14.23 g, 65.2 mmol) are gently added.…”

Section: Methodsmentioning

confidence: 99%

Voxelated bioprinting of modular double-network bio-ink droplets

Zhu,

He,

Wang

et al. 2024

Nat Commun

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Analogous of pixels to two-dimensional pictures, voxels—in the form of either small cubes or spheres—are the basic building blocks of three-dimensional objects. However, precise manipulation of viscoelastic bio-ink voxels in three-dimensional space represents a grand challenge in both soft matter science and biomanufacturing. Here, we present a voxelated bioprinting technology that enables the digital assembly of interpenetrating double-network hydrogel droplets made of polyacrylamide/alginate-based or hyaluronic acid/alginate-based polymers. The hydrogels are crosslinked via additive-free and biofriendly click reaction between a pair of stoichiometrically matched polymers carrying norbornene and tetrazine groups, respectively. We develop theoretical frameworks to describe the crosslinking kinetics and stiffness of the hydrogels, and construct a diagram-of-state to delineate their mechanical properties. Multi-channel print nozzles are developed to allow on-demand mixing of highly viscoelastic bio-inks without significantly impairing cell viability. Further, we showcase the distinctive capability of voxelated bioprinting by creating highly complex three-dimensional structures such as a hollow sphere composed of interconnected yet distinguishable hydrogel particles. Finally, we validate the cytocompatibility and in vivo stability of the printed double-network scaffolds through cell encapsulation and animal transplantation.

show abstract

Section: Methodsmentioning

confidence: 99%

Voxelated bioprinting of modular double-network bio-ink droplets

Zhu,

He,

Wang

et al. 2024

Nat Commun

View full text Add to dashboard Cite

show abstract

“…CI is prepared following a previously reported procedure 37 with minor modifications. To a solution of 4-(aminomethyl)benzonitrile hydrochloride (10.00 g, 59.3 mmol) in dichloromethane (250 mL), triethylamine (20.7 mL, 148.25 mmol) and Boc 2 O (14.23 g, 65.2 mmol) are gently added.…”

Section: Methodsmentioning

confidence: 99%

“…CII is prepared following a previously reported procedure 37 with modifications during post- processing. CI (2.00 g, 8.6 mmol), acetonitrile (4.5 mL, 86.0 mmol), Ni(OTf) 2 (1.53 g, 4.3 mmol), and hydrazine (13.8 mL, 430.0 mmol) are added to a 60 mL high pressure tube (ACE GLASS, Sigma-Aldrich, Cat.…”

Section: Methodsmentioning

confidence: 99%

Voxelated bioprinting of modular double-network bio-ink droplets

Zhu,

He,

Wang

et al. 2023

Preprint

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Analogous of pixels to two-dimensional pictures, voxels -- in the form of either small cubes or spheres -- are the basic building blocks of three-dimensional (3D) objects. However, precise manipulation of viscoelastic bio-ink voxels in 3D space represents a grand challenge in both soft matter science and biomanufacturing. Here, we present a voxelated bioprinting technology that enables the digital assembly of interpenetrating alginate and polyacrylamide (PAM) double-network (DN) hydrogel droplets. The hydrogel is crosslinked via additive-free bioorthogonal chemistry involving a pair of stoichiometrically matched polymers. We develop theoretical frameworks to describe the crosslinking kinetics and stiffness of the hydrogels, and construct a diagram-of-state to delineate their mechanical properties. Multi-channel print nozzles are developed to allow on-demand mixing of highly viscoelastic bio-inks without significantly impairing cell viability. Further, we showcase the distinctive capability of voxelated bioprinting by creating highly complex 3D structures such as a hollow sphere composed of interconnected yet distinguishable hydrogel particles. Finally, we validate the cytocompatibility and in vivo stability of the printed DN scaffolds through cell encapsulation and animal transplantation.

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“…Recently, inverse electron-demand Diels-Alder reaction has been applied for the preparation of POCs [ 314 ]. The authors used 7-oxanorbornene as a dienophile and tetrazine as a diene.…”

Section: Post-synthetic Conjugation Approachesmentioning

confidence: 99%

Chemistry of Peptide-Oligonucleotide Conjugates: A Review

2021

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Peptide-oligonucleotide conjugates (POCs) represent one of the increasingly successful albeit costly approaches to increasing the cellular uptake, tissue delivery, bioavailability, and, thus, overall efficiency of therapeutic nucleic acids, such as, antisense oligonucleotides and small interfering RNAs. This review puts the subject of chemical synthesis of POCs into the wider context of therapeutic oligonucleotides and the problem of nucleic acid drug delivery, cell-penetrating peptide structural types, the mechanisms of their intracellular transport, and the ways of application, which include the formation of non-covalent complexes with oligonucleotides (peptide additives) or covalent conjugation. The main strategies for the synthesis of POCs are viewed in detail, which are conceptually divided into (a) the stepwise solid-phase synthesis approach and (b) post-synthetic conjugation either in solution or on the solid phase, especially by means of various click chemistries. The relative advantages and disadvantages of both strategies are discussed and compared.

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Inverse Electron-Demand Diels–Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles

Cited by 14 publications

References 33 publications

Voxelated bioprinting of modular double-network bio-ink droplets

Voxelated bioprinting of modular double-network bio-ink droplets

Voxelated bioprinting of modular double-network bio-ink droplets

Chemistry of Peptide-Oligonucleotide Conjugates: A Review

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