Evidence map›Paper›PMID 32037819›Full record

ArticleJournal of the American Chemical Society2020

Photolabile Linkers: Exploiting Labile Bond Chemistry to Control Mode and Rate of Hydrogel Degradation and Protein Release.

Paige J LeValley, Raghupathi Neelarapu, Bryan P Sutherland, Srimoyee Dasgupta, Christopher J Kloxin, April M Kloxin

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.

0numbers the graph read from it
0cells of the map it votes in
32citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

32 citing papers in PubMed.

  1. Review
  2. Article
  3. Article
  4. Journal of the American Chemical Society · 2025
    Article
  5. Review
  6. Photo-Triggered Hyaluronic Acid Hydrogel for 3D Culture and Cell Recovery.Chembiochem : a European journal of chemical biology · 2025
    Article
  7. Article
  8. Recent Developments in Nanoparticle-Hydrogel Hybrid Materials for Controlled Release.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Review
  9. Review
  10. Article
  11. Review
  12. Article
  13. Article
  14. Review
  15. Article
  16. Review
  17. Article
  18. Article
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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors.

Paige J LeValleyDepartment of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States.
Raghupathi NeelarapuDepartment of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Bryan P SutherlandDepartment of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States.ORCID 0000-0002-1583-4601
Srimoyee DasguptaDepartment of Material Science and Engineering, University of Delaware, Newark, Delaware 19716, United States.
Christopher J KloxinDepartment of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States.ORCID 0000-0002-1679-0022
April M KloxinDepartment of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States.ORCID 0000-0002-4594-2953

Funding

This renovation project will create over 1455 sq. ft. of state- of-the-art reseaP20GM104316 · NIGMS · UNIVERSITY OF DELAWARE · PI FOX, JOSEPH M · 2014 to 2024
$26.8M
Pilot Research Subproject ProgramP30GM110758 · NIGMS · UNIVERSITY OF DELAWARE · PI BEEBE, THOMAS PAUL · 2014 to 2018
$5.8M
NIGMS NIH HHS P20 GM104316NIGMS NIH HHS P30 GM110758
6 · The paper itself

Abstract

Photolabile moieties have been utilized in applications ranging from peptide synthesis and controlled protein activation to tunable and dynamic materials. The photochromic properties of nitrobenzyl (NB) based linkers are readily tuned to respond to cytocompatible light doses and are widely utilized in cell culture and other biological applications. While widely utilized, little is known about how the microenvironment, particularly confined aqueous environments (e.g., hydrogels), affects both the mode and rate of cleavage of NB moieties, leading to unpredictable limitations in control over system properties (e.g., rapid hydrolysis or slow photolysis). To address these challenges, we synthesized and characterized the photolysis and hydrolysis of NB moieties containing different labile bonds (i.e., ester, amide, carbonate, or carbamate) that served as labile crosslinks within step-growth hydrogels. We observed that NB ester bond exhibited significant rates of both photolysis and hydrolysis, whereas, importantly, the NB carbamate bond had superior light responsiveness and resistance to hydrolysis within the hydrogel microenvironment. Exploiting this synergy and orthogonality of photolytic and hydrolytic degradation, we designed concentric cylinder hydrogels loaded with different cargoes (e.g., model protein with different fluorophores) for either combinatorial or sequential release, respectively. Overall, this work provides new facile chemical approaches for tuning the degradability of NB linkers and an innovative strategy for the construction of multimodal degradable hydrogels, which can be utilized to guide the design of not only tunable materials platforms but also controlled synthetic protocols or surface modification strategies.

Indexed as

AnimalsCarbamatesCattleDrug Delivery SystemsDrug LiberationFluorescent DyesHydrogelsHydrolysisNitrobenzenesPhotolysisProof of Concept StudySerum Albumin, BovineUltraviolet RaysCarbamatesFluorescent DyesHydrogelsNitrobenzenesSerum Albumin, Bovine

Identifiers

PMID32037819
PMCPMC7267699

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.