The effect of DOPA hydroxyl groups on wet adhesion to polystyrene surface: An experimental and theoretical study

Mussels wet adhesive performance has been arousing curiosity for a long time. It is found that 3,4-dihydroxyphenylalanine (DOPA) is responsible for adhesive properties of mussels. Despite a large body of research characterizing the interactions DOPA with hydrophilic surfaces, relatively few works ha...

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Bibliographic Details
Published in:Materials chemistry and physics 2020-03, Vol.243, p.122606, Article 122606
Main Authors: Yildiz, Remziye, Ozen, Sercan, Sahin, Hasan, Akdogan, Yasar
Format: Article
Language:English
Subjects:
Adhesion
Adhesives
Amino acids
Benzene
Catechol
Density functional theory
DFT calculations
Dihydroxyphenylalanine
DOPA
Electron paramagnetic resonance
Electron spin
EPR spectroscopy
Hydrophobicity
Hydroxyl groups
Molecular dynamics
Mussel adhesion
Mussels
Phenylalanine
Polystyrene resins
Surface coverage
Tyrosine
Water chemistry
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Summary:Mussels wet adhesive performance has been arousing curiosity for a long time. It is found that 3,4-dihydroxyphenylalanine (DOPA) is responsible for adhesive properties of mussels. Despite a large body of research characterizing the interactions DOPA with hydrophilic surfaces, relatively few works have addressed the mechanism of interactions with hydrophobic surfaces. The benzene ring of DOPA is the main attributor to the adhesion on hydrophobic polystyrene (PS) surface. However, here we showed that two hydroxyl groups of catechol have also effects on wet adhesion. We studied wet adhesive properties of DOPA, tyrosine and phenylalanine functionalized PEG polymers, PEG-(N-Boc-l-DOPA)4, PEG-(N-Boc-l-Tyrosine)4, PEG-(N-Boc-l-Phenylalanine)4, on spin labeled PS nanobeads (SL-PS) by electron paramagnetic resonance (EPR) spectroscopy. Surface coverage ratio of SL-PS upon additions of PEG-(N-Boc-l-DOPA)4, PEG-(N-Boc-l-Tyrosine)4 and PEG-(N-Boc-l-Phenylalanine)4 showed that SL-PS was covered with 70%, 50% and 0%, respectively. This showed that spontaneous wet adhesion on PS increases with the number of amino acids hydroxyl groups. This is also supported with the density functional theory (DFT) energy calculations and ab-initio molecular dynamics (AIMD) simulations. In water, interactions between water molecules and hydroxyl groups on the catechol induce catechol adhesion via π-π stacking between the catechol and double styrene rings which were already tilted out with water. [Display omitted] •Hydroxyl groups in DOPA play a crucial role on the adhesion to wet styrene surface.•DOPA or tyrosine ended PEG covered the styrene surface but not with phenylalanine.•Without water, catechol has the lowest adhesion ability to the styrene surface.•EPR spectroscopy provides the degree of surface coverage of nanoparticles in water.•AIMD simulations with and without water support the EPR results.
ISSN:0254-0584
1879-3312
DOI:10.1016/j.matchemphys.2019.122606