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Cited by 315Hydrogels: synthesis, properties, applicationsPhotopolymerization techniques and applicationsClick Chemistry and Applications

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Photoreversible Patterning of Biomolecules within Click‐Based Hydrogels

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DeForest, Cole A., Anseth, Kristi S.·2012·Angewandte Chemie International Edition
DOI 10.1002/anie.201106463PMC PMC3430005
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Abstract

Lighting the way: Biochemical cues have been reversibly patterned into hydrogels with full spatiotemporal control by using two photochemical reactions. The hydrogel is conjugated with a peptide by a thiol-ene photoaddition reaction that is initiated by visible light. Subsequent, selective photocleavage of an o-nitrobenzyl ether with UV light enables dynamic presentation of the peptide to cells with control in three dimensions.

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Figures

Figure 1 a) Hydrogels were formed from PEG tetracyclooctyne (Mn=ca. 10 000 Da, (2)) and N3-RGK(alloc)GRK(N3)-NH2 (3). The alloc groups were functionalized with the fluorescent peptide Ac-C-(PL)-RGDSK(AF488)-NH2 (1) through thiol-ene photoreaction and unfunctionalized through o-nitrobenzyl ether photocleavage. b) Representation of the thiol-ene conjugation reaction (top), the o-nitrobenzyl ether cleavage reaction (middle), and the overall hydrogel structure and reversible patterning approach (bottom). c) Concentrations of peptide 1 patterned by thiol-ene reaction as a function of the initiator concentration (▴=2.5 μm, □=5 μm, •=10 μm) and visible light exposure time. d) Experimentally-determined and predicted concentrations (lines) of 1 based on the photocleavage kinetics from Eq. (1) as a function of UV light intensity (•=5 mW cm−2, □=10 mW cm−2, ▴=20 mW cm−2) and exposure time.
Figure 1 a) Hydrogels were formed from PEG tetracyclooctyne (Mn=ca. 10 000 Da, (2)) and N3-RGK(alloc)GRK(N3)-NH2 (3). The alloc groups were functionalized with the fluorescent peptide Ac-C-(PL)-RGDSK(AF488)-NH2 (1) through thiol-ene photoreaction and unfunctionalized through o-nitrobenzyl ether photocleavage. b) Representation of the thiol-ene conjugation reaction (top), the o-nitrobenzyl ether cleavage reaction (middle), and the overall hydrogel structure and reversible patterning approach (bottom). c) Concentrations of peptide 1 patterned by thiol-ene reaction as a function of the initiator concentration (▴=2.5 μm, □=5 μm, •=10 μm) and visible light exposure time. d) Experimentally-determined and predicted concentrations (lines) of 1 based on the photocleavage kinetics from Eq. (1) as a function of UV light intensity (•=5 mW cm−2, □=10 mW cm−2, ▴=20 mW cm−2) and exposure time.CC BY · PubMed Central
Figure 2 Thiol-ene patterning of the fluorescent peptide Ac-C-(PL)-RGDSK(AF488)-NH2 (1) into the hydrogel a) in 2D throughout the gel after exposure to masked visible light and b) in 3D after exposure to focused pulsed laser light. False coloring is used for enhanced visualization. c) and d) Subsets of the pre-patterned cues were removed by exposure to UV light to modify the original chemical pattern and yield new 2D and 3D patterns. Scale bars=200 μm.
Figure 2 Thiol-ene patterning of the fluorescent peptide Ac-C-(PL)-RGDSK(AF488)-NH2 (1) into the hydrogel a) in 2D throughout the gel after exposure to masked visible light and b) in 3D after exposure to focused pulsed laser light. False coloring is used for enhanced visualization. c) and d) Subsets of the pre-patterned cues were removed by exposure to UV light to modify the original chemical pattern and yield new 2D and 3D patterns. Scale bars=200 μm.CC BY · PubMed Central
Figure 3 Ac-C-(PL)-RGDSK(AF488)-NH2 (1) was patterned into hydrogels by using unmasked light (panels (a), (b), and (d)) or a mask that contains 200 μm slits spaced 200 μm apart (panels (c), (e)). The prepatterned samples were subsequently exposed to gradients of UV light that were generated by a moving opaque photomask (1.6, 0.8, or 0.4 mm min−1 for (a); 0.4 mm min−1 for (b–e)) to induce photodegradation of the PL moiety and to create exponentially decaying peptide gradients. By shuttering the light (panel (b)) or releasing pre-patterned lines (panels (c), (e)), unique gradients in the peptide concentration were generated across the network. Solid gray lines are predicted concentrations based on predetermined photocleavage kinetics from Eq (1). Scale bars=400 μm.
Figure 3 Ac-C-(PL)-RGDSK(AF488)-NH2 (1) was patterned into hydrogels by using unmasked light (panels (a), (b), and (d)) or a mask that contains 200 μm slits spaced 200 μm apart (panels (c), (e)). The prepatterned samples were subsequently exposed to gradients of UV light that were generated by a moving opaque photomask (1.6, 0.8, or 0.4 mm min−1 for (a); 0.4 mm min−1 for (b–e)) to induce photodegradation of the PL moiety and to create exponentially decaying peptide gradients. By shuttering the light (panel (b)) or releasing pre-patterned lines (panels (c), (e)), unique gradients in the peptide concentration were generated across the network. Solid gray lines are predicted concentrations based on predetermined photocleavage kinetics from Eq (1). Scale bars=400 μm.CC BY · PubMed Central
Figure 4 a) Parallel lines (200 μm wide) of Ac-C-(PL)-RGDSK(AF488)-NH2 (1) were patterned into the hydrogel at 1.0 mm by visible thiol-ene photocoupling. Seeded NIH 3T3 cells only adhered to regions of the hydrogel surface that were functionalized with 1. b) Localized cell-detachment was observed upon spatial removal (24 hours post-seeding) of RGD through masked UV light exposure. Green=RGD (1), red=F-actin, blue=nuclei. Scale bar=200 μm.
Figure 4 a) Parallel lines (200 μm wide) of Ac-C-(PL)-RGDSK(AF488)-NH2 (1) were patterned into the hydrogel at 1.0 mm by visible thiol-ene photocoupling. Seeded NIH 3T3 cells only adhered to regions of the hydrogel surface that were functionalized with 1. b) Localized cell-detachment was observed upon spatial removal (24 hours post-seeding) of RGD through masked UV light exposure. Green=RGD (1), red=F-actin, blue=nuclei. Scale bar=200 μm.CC BY · PubMed Central

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Metadata

Authors
DeForest, C. A., & Anseth, K. S.
Affiliations
Howard Hughes Medical Institute (US)
Corresponding author
Anseth, Kristi S.
ORCID
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2011-12-08
Volume
51
Issue
8
Pages
1816-1819
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
DOI
10.1002/anie.201106463
PMC
PMC3430005
OpenAlex
W2109351872
Cited by
315
References
24
Citations by year
2026: 9 · 2025: 7 · 2024: 12 · 2023: 11 · 2022: 21 · 2021: 23 · 2020: 20 · 2019: 18 · 2018: 38 · 2017: 27 · 2016: 18 · 2015: 22 · 2014: 33 · 2013: 35 · 2012: 21
FWCI
12.99
Type
journal article
Language
en
Open access
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations
  • Angewandte Chemie International Edition (publishedVersion)
  • Europe PMC (PubMed Central) (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
Funders
  • National Science Foundation (1006711)
  • Howard Hughes Medical Institute
Topics
  • Physical Sciences › Materials Science › Biomaterials › Hydrogels: synthesis, properties, applications
  • Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
  • Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
Keywords
hydrogels, click chemistry, peptide conjugation, photocleavage, spatiotemporal control, 3D cell culture
MeSH terms
Oligopeptides, Peptides, Molecular Structure, Hydrogels, Photochemical Processes, Click Chemistry

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