Tough and On‐Demand Detachable Wet Tissue Adhesive Hydrogel Made from Catechol Derivatives with a Long Aliphatic Side Chain

Wet adhesion is critical in cases of wound closure, but it is usually deterred by the hydration layer on tissues. Inspired by dopamine-mediated underwater adhesion in mussel foot proteins, wet tissue adhesives containing catechol with 2-3 carbons side chains are reported mostly. To make wet adhesion of this type of adhesives much tougher, catechol derivatives with a long aliphatic side chain (≈10 atoms length) are synthesized. Then, a series of strong wet tissue adhesive hydrogels are prepared through photoinduced copolymerization of acrylic acid with synthetic monomers. The adhesive hydrogel has a high cohesion strength, that is, tensile strength and strain, and toughness of ≈1800 kPa, ≈540%, and ≈4100 kJ m-3 , respectively. Its interfacial toughness on wet and underwater porcine skin is respectively ≈1300 and ≈1100 J m-2 , and its adhesion strength to wet porcine skin is ≈153 kPa. These values are much higher than those of dopamine-based adhesives in the same conditions, demonstrating that the long aliphatic side chain on catechol can greatly improve the wet tissue-adhesion. Additionally, the tough interfacial adhesion can be broken on demand with 5 wt.% aqueous urea solution. This adhesive hydrogel is highly promising in safe wound closure.

[1]  Haiqing Liu,et al.  Mussel Foot Protein Inspired Tape‐Type Adhesive with Water‐Responsive, High Conformal, Tough, and On‐Demand Detachable Adhesion to Wet Tissue , 2023, Advanced healthcare materials.

[2]  Shutao Wang,et al.  Bioinspired chemical design to control interfacial wet adhesion , 2023, Chem.

[3]  T. Guo,et al.  Tuning Water-Resistant Networks in Mussel-Inspired Hydrogels for Robust Wet Tissue and Bioelectronic Adhesion. , 2023, ACS nano.

[4]  Seung‐Woo Cho,et al.  pH-Universal Catechol-Amine Chemistry for Versatile Hyaluronic Acid Bioadhesives. , 2022, Small.

[5]  Yongyuan Ren,et al.  Tough Hydrogels with Isotropic and Unprecedented Crack Propagation Resistance , 2022, Advanced Functional Materials.

[6]  Yaxin Guo,et al.  Tough Wet Adhesion of Hydrogen-Bond-Based Hydrogel with On-Demand Debonding and Efficient Hemostasis. , 2022, ACS applied materials & interfaces.

[7]  D. Mooney,et al.  Rapid Ultratough Topological Tissue Adhesives , 2022, Advanced materials.

[8]  Haiqing Liu,et al.  Water-driven noninvasively detachable wet tissue adhesives for wound closure , 2022, Materials today. Bio.

[9]  Chun-peng Wang,et al.  Lignin-containing hydrogel matrices with enhanced adhesion and toughness for all-hydrogel supercapacitors , 2022, Chemical Engineering Journal.

[10]  Bruce P. Lee,et al.  pH Responsive Antibacterial Hydrogel Utilizing Catechol-Boronate Complexation Chemistry. , 2022, Chemical engineering journal.

[11]  M. Ye,et al.  A Skin‐Like Pressure‐ and Vibration‐Sensitive Tactile Sensor Based on Polyacrylamide/Silk Fibroin Elastomer , 2022, Advanced Functional Materials.

[12]  X. Chen,et al.  Tough Hydrogel Bioadhesives for Sutureless Wound Sealing, Hemostasis and Biointerfaces , 2021, Advanced Functional Materials.

[13]  Z. Suo,et al.  Fracture, fatigue, and friction of polymers in which entanglements greatly outnumber cross-links , 2021, Science.

[14]  Lan Li,et al.  Hydrogel tapes for fault-tolerant strong wet adhesion , 2021, Nature Communications.

[15]  Guangyu Bao,et al.  Multifaceted Design and Emerging Applications of Tissue Adhesives , 2021, Advanced materials.

[16]  Bo Li,et al.  Genetically Engineered Polypeptide Adhesive Coacervates for Surgical Applications , 2021, Angewandte Chemie.

[17]  Lei Jiang,et al.  A Spider‐Silk‐Inspired Wet Adhesive with Supercold Tolerance , 2021, Advanced materials.

[18]  Haeshin Lee,et al.  Coagulopathy-independent, bioinspired hemostatic materials: A full research story from preclinical models to a human clinical trial , 2021, Science Advances.

[19]  Yi-Chen Li,et al.  Tissue Adhesives: From Research to Clinical Translation. , 2021, Nano today.

[20]  D. Mooney,et al.  Polymeric Tissue Adhesives. , 2021, Chemical reviews.

[21]  Jiayi Liu,et al.  Tough Underwater Super-tape Composed of Semi-interpenetrating Polymer Networks with a Water-Repelling Liquid Surface. , 2020, ACS applied materials & interfaces.

[22]  Lu Lai,et al.  Dual Physically Cross‐Linked Hydrogels Incorporating Hydrophobic Interactions with Promising Repairability and Ultrahigh Elongation , 2020, Advanced Functional Materials.

[23]  Zhong Lin Wang,et al.  Bioinspired Self‐Healing Human–Machine Interactive Touch Pad with Pressure‐Sensitive Adhesiveness on Targeted Substrates , 2020, Advanced materials.

[24]  Yong Han,et al.  Degradable Gelatin-Based IPN Cryogel Hemostat for Rapidly Stopping Deep Noncompressible Hemorrhage and Simultaneously Improving Wound Healing , 2020 .

[25]  Xuanhe Zhao,et al.  Instant tough bioadhesive with triggerable benign detachment , 2020, Proceedings of the National Academy of Sciences.

[26]  Weikang Zhou,et al.  An Anti-Freezing/Anti-Heating Hydrogel Containing Catechol Derivative Urushiol for Strong Wet Adhesion to Various Substrates. , 2020, ACS applied materials & interfaces.

[27]  P. Wieringa,et al.  Bioprinting: From Tissue and Organ Development to in Vitro Models , 2020, Chemical reviews.

[28]  Xiong Lu,et al.  Mussel‐Inspired Hydrogels for Self‐Adhesive Bioelectronics , 2020, Advanced Functional Materials.

[29]  Weilin Xu,et al.  Dopamine-modified Hyaluronic Acid Hydrogels Adhesives with Fast-forming and High Tissue Adhesion. , 2020, ACS applied materials & interfaces.

[30]  Natalie Artzi,et al.  Overcoming the translational barriers of tissue adhesives , 2020, Nature Reviews Materials.

[31]  Jiandu Lei,et al.  Autonomic Self-Healing Silk Fibroin Injectable Hydrogels Formed via Surfactant-Free Hydrophobic Association. , 2019, ACS applied materials & interfaces.

[32]  Wenguang Liu,et al.  Water‐Triggered Hyperbranched Polymer Universal Adhesives: From Strong Underwater Adhesion to Rapid Sealing Hemostasis , 2019, Advanced materials.

[33]  H. Ouyang,et al.  A strongly adhesive hemostatic hydrogel for the repair of arterial and heart bleeds , 2019, Nature Communications.

[34]  Z. Suo,et al.  Hydrogel Adhesion: A Supramolecular Synergy of Chemistry, Topology, and Mechanics , 2019, Advanced Functional Materials.

[35]  Bruce P. Lee,et al.  Multifunctional Biomedical Adhesives , 2019, Advanced healthcare materials.

[36]  A. E. Ehret,et al.  Tear resistance of soft collagenous tissues , 2019, Nature Communications.

[37]  D. Collins,et al.  Systematic review of fibrin glue in burn wound reconstruction , 2019, The British journal of surgery.

[38]  F. Busqué,et al.  The Chemistry behind Catechol-Based Adhesion. , 2018, Angewandte Chemie.

[39]  Qianhui Liu,et al.  Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive , 2018, ACS central science.

[40]  Marleen Kamperman,et al.  Bioinspired Underwater Adhesives by Using the Supramolecular Toolbox , 2018, Advanced materials.

[41]  Shifang Zhao,et al.  Mechanically Reinforced Catechol-Containing Hydrogels with Improved Tissue Gluing Performance , 2017, Biomimetics.

[42]  Yonglan Liu,et al.  Super Bulk and Interfacial Toughness of Physically Crosslinked Double‐Network Hydrogels , 2017 .

[43]  Ali Khademhosseini,et al.  Engineering a highly elastic human protein–based sealant for surgical applications , 2017, Science Translational Medicine.

[44]  D J Mooney,et al.  Tough adhesives for diverse wet surfaces , 2017, Science.

[45]  Qin Zhang,et al.  Bioinspired Adhesive Hydrogel Driven by Adenine and Thymine. , 2017, ACS applied materials & interfaces.

[46]  J. Israelachvili,et al.  Microphase Behavior and Enhanced Wet-Cohesion of Synthetic Copolyampholytes Inspired by a Mussel Foot Protein. , 2015, Journal of the American Chemical Society.

[47]  Soong Ho Um,et al.  Tissue Adhesive Catechol‐Modified Hyaluronic Acid Hydrogel for Effective, Minimally Invasive Cell Therapy , 2015 .

[48]  Hongbo Zeng,et al.  Novel Mussel‐Inspired Injectable Self‐Healing Hydrogel with Anti‐Biofouling Property , 2015, Advanced materials.

[49]  T. Lu,et al.  Self-Assembling Multi-Component Nanofibers for Strong Bioinspired Underwater Adhesives , 2014, Nature nanotechnology.

[50]  J. Herbert Waite,et al.  Hydrophobic enhancement of Dopa-mediated adhesion in a mussel foot protein. , 2013, Journal of the American Chemical Society.

[51]  P. Messersmith,et al.  Biological performance of mussel-inspired adhesive in extrahepatic islet transplantation. , 2010, Biomaterials.