pH-Tolerant Wet Adhesion of Catechol Analogs

被引：0

作者：

Degen, George D. ^{[1
]}

Ahmed, Syeda Tajin ^{[2
]}

Stow, Parker R. ^{[3
]}

Butler, Alison ^{[3
]}

Eguiluz, Roberto C. Andresen ^{[2
,4
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem Engn, Santa Barbara, CA 93106 USA

[2] Univ Calif Merced, Dept Mat Sci & Engn, Merced, CA 95344 USA

[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[4] Univ Calif Merced, Hlth Sci Res Inst, Merced, CA 95344 USA

来源：

ACS APPLIED MATERIALS & INTERFACES | 2024年 / 16卷 / 17期

基金：

美国国家科学基金会;

关键词：

wet adhesion; DOPA; HOPO; pH tolerantadhesive; mussel-inspired; surface forces apparatus; surface primers; CROSS-LINKING; MUSSEL; MECHANICS; OXIDATION; HYDROGELS; SYNERGY; MICA;

D O I：

10.1021/acsami.4c01740

中图分类号：

TB3 [工程材料学];

学科分类号：

0805 ; 080502 ;

摘要：

The need for improved wet adhesives has driven research on mussel-inspired materials incorporating dihydroxyphenylalanine (DOPA) and related analogs of the parent catechol, but their susceptibility to oxidation limits practical application of these functionalities. Here, we investigate the molecular-level adhesion of the catechol analogs dihydroxybenzamide (DHB) and hydroxypyridinone (HOPO) as a function of pH. We find that the molecular structure of the catechol analogs influences their susceptibility to oxidation in alkaline conditions, with HOPO emerging as a particularly promising candidate for pH-tolerant adhesives for diverse environmental conditions.

引用

页码：22689 / 22695

页数：7

共 44 条

[1] Biomimetic Adhesive Micropatterned Hydrogel Patches for Drug Release [J].

Amaral, Katia R. ;

Silva, A. Sofia ;

Santos, Lucia F. ;

Castanheira, Edgar J. ;

Mendes, Maria C. ;

Costa, Dora C. S. ;

Rodrigues, Joao M. M. ;

Marto, Joana ;

Mano, Joao F. .

ADVANCED HEALTHCARE MATERIALS, 2023, 12 (28)

[2] Influence of Electronegative Substituents on the Binding Affinity of Catechol-Derived Anchors to Fe3O4 Nanoparticles [J].

Amstad, Esther ;

Gehring, Andreas U. ;

Fischer, Hakon ;

Nagaiyanallur, Venkatamaran V. ;

Haehner, Georg ;

Textor, Marcus ;

Reimhult, Erik .

JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (03) :683-691

[3] Ultrastable Iron Oxide Nanoparticle Colloidal Suspensions Using Dispersants with Catechol-Derived Anchor Groups [J].

Amstad, Esther ;

Gillich, Torben ;

Bilecka, Idalia ;

Textor, Marcus ;

Reimhult, Erik .

NANO LETTERS, 2009, 9 (12) :4042-4048

[4] Mussel-Inspired Self-Healing Double-Cross-Linked Hydrogels by Controlled Combination of Metal Coordination and Covalent Cross-Linking [J].

Andersen, Amanda ;

Krogsgaard, Marie ;

Birkedal, Henrik .

BIOMACROMOLECULES, 2018, 19 (05) :1402-1409

[5]

[Anonymous], 1985, CONTACT MECH

[6] Marine-inspired polymers in medical adhesion [J].

Balkenende, Diederik W. R. ;

Winkler, Sally M. ;

Messersmith, Phillip B. .

EUROPEAN POLYMER JOURNAL, 2019, 116 :134-143

[7] Synthesis and evaluation of the bis-nor-anachelin chromophore as potential cyanobacterial ligand [J].

Bethuel, Y ;

Gademann, K .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6258-6264

[8] Effect of Nitro-Functionalization on the Cross-Linking and Bioadhesion of Biomimetic Adhesive Moiety [J].

Cencer, Morgan ;

Murley, Meridith ;

Liu, Yuan ;

Lee, Bruce P. .

BIOMACROMOLECULES, 2015, 16 (01) :404-410

[9] Dopamine-Based Coatings and Hydrogels: Toward Substitution-Related Structure-Property Relationships [J].

Cui, Jiaxi ;

Iturri, Jagoba ;

Paez, Julieta ;

Shafiq, Zahid ;

Serrano, Cristina ;

d'Ischia, Marco ;

del Campo, Arynzazu .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 2014, 215 (24) :2403-2413

[10] Hydroxypyridinone Chelators: From Iron Scavenging to Radiopharmaceuticals for PET Imaging with Gallium-68 [J].

Cusnir, Ruslan ;

Imberti, Cinzia ;

Hider, Robert C. ;

Blower, Philip J. ;

Ma, Michelle T. .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2017, 18 (01)

← 1 2 3 4 5 →