ArticleBiomacromolecules2015
Effect of nitro-functionalization on the cross-linking and bioadhesion of biomimetic adhesive moiety.
Article in Biomacromolecules, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 76 citations in OpenAlex.
- Lighting up Polynitrodopamine: from Electropolymerization to Photopatterning of Ultrathin Films.ACS applied materials & interfaces · 2026Article
- Autoxidation-Induced Curing of 6-Hydroxycatechol-Containing Adhesive.Macromolecular chemistry and physics · 2025Article
- Biocompatible Cobalt Oxide Nanoparticles for X-ray Fluorescence Microscopy.Research square · 2024Article
- pH-Tolerant Wet Adhesion of Catechol Analogs.ACS applied materials & interfaces · 2024Article
- Strongly Metal-Adhesive and Self-Healing Gelatin@Polydopamine-Based Hydrogels with Long-Term Antioxidant Activity.Antioxidants (Basel, Switzerland) · 2023Article
- Utilizing Robust Design to Optimize Composite Bioadhesive for Promoting Dermal Wound Repair.Polymers · 2023Article
- Mussel-inspired biomaterials: From chemistry to clinic.Bioengineering & translational medicine · 2022Review
- Optimization of the Elasticity and Adhesion of Catechol- or Dopamine-Loaded Gelatin Gels under Oxidative Conditions.Gels (Basel, Switzerland) · 2022Article
- Mapping out the Aqueous Surface Chemistry of Metal Oxide Nanocrystals: Carboxylate, Phosphonate, and Catecholate Ligands.JACS Au · 2022Article
- Tannic acid: a crosslinker leading to versatile functional polymeric networks: a review.RSC advances · 2022Review
- Oxidation Chemistry of Catechol Utilized in Designing Stimuli-Responsive Adhesives and Antipathogenic Biomaterials.ACS omega · 2021Review
- In Situ Deactivation of Catechol-Containing Adhesive Using Electrochemistry.Journal of the American Chemical Society · 2020Article
- Correlating the mass and mechanical property changes during the degradation of PEG-based adhesive.Journal of applied polymer science · 2020Article
- Mussel-inspired bioadhesives in healthcare: design parameters, current trends, and future perspectives.Biomaterials science · 2020Review
- Catechol-functionalized hydrogels: biomimetic design, adhesion mechanism, and biomedical applications.Chemical Society reviews · 2020Article
- Multifunctional Biomedical Adhesives.Advanced healthcare materials · 2019Review
- Article
- Biodegradable Nanoparticles Enhanced Adhesiveness of Mussel-Like Hydrogels at Tissue Interface.Advanced healthcare materials · 2018Article
- Effect of incorporating clustered silica nanoparticles on the performance and biocompatibility of catechol-containing PEG-based bioadhesive.Biomedical materials (Bristol, England) · 2018Article
- Scarless Wound Closure by a Mussel-Inspired Poly(amidoamine) Tissue Adhesive with Tunable Degradability.ACS omega · 2017Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Dopamine mimics the exceptional moisture-resistant adhesive properties of the amino acid, DOPA, found in adhesive proteins secreted by marine mussels. The catechol side chain of dopamine was functionalized with a nitro-group, and the effect of the electron withdrawing group modification on the cross-linking chemistry and bioadhesive properties of the adhesive moiety was evaluated. Both nitrodopamine and dopamine were covalently attached as a terminal group onto an inert, 4-armed poly(ethylene glygol) (PEG-ND and PEG-D, respectively). PEG-ND and PEG-D exhibited different dependence on the concentration of NaIO4 and pH, which affected the curing rate, mechanical properties, and adhesive performance of these biomimetic adhesives differently. PEG-ND cured instantly and its bioadhesive properties were minimally affected by the change in pH (5.7-8) within the physiological range. Under mildly acidic conditions (pH 5.7 and 6.7), PEG-ND outperformed PEG-D in lap shear adhesion testing using wetted pericardium tissues. However, nitrodopamine only formed dimers, which resulted in the formation of loosely cross-linked network and adhesive with reduced cohesive properties. UV-vis spectroscopy further confirmed nitrodopamine's ability for rapid dimer formation. The ability for nitrodopamine to rapidly cure and adhere to biological substrates in an acidic pH make it suitable for designing adhesive biomaterials targeted at tissues that are more acidic (i.e., subcutaneous, dysoxic, or tumor tissues).
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Registered trials
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.