Hydrogen Bond Interaction Driven Procyanidine Assembly into Underwater Adhesive with Antibacterial Activity

doi:10.19894/j.issn.1000-0518.220017

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (10): 1533-1542.DOI: 10.19894/j.issn.1000-0518.220017

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Hydrogen Bond Interaction Driven Procyanidine Assembly into Underwater Adhesive with Antibacterial Activity

Xiao-Ming XIE¹(), Jia-Qi ZHANG²()

^1.Department of Chemistry，Xinzhou Teachers University，Xinzhou 034000，China
^2.College of Physics and Optoelectronics，Taiyuan University of Technology，Taiyuan 030024，China

Received:2022-01-18 Accepted:2022-04-18 Published:2022-10-01 Online:2022-10-05
Contact: Xiao-Ming XIE,Jia-Qi ZHANG
About author:zjq18734238044@163.com
xiexm0910@163.com；
Supported by:
the Natural Science Foundation of Shanxi Province(20210302124339);the Science and Technology Innovation Project of Colleges and Universities in Shanxi Province(2021L452);the Research Fund of Xinzhou Teachers University(2020KY03)

Abstract

Abstract:

The demand of biomimetic underwater adhesives in biomedical and engineering applications is getting larger and larger. However， most of the reported preparation methods of biomimetic adhesives usually require complex chemical coupling or modification， and expensive constructing motifs. In this study， we develop a simple and economical construction strategy for the preparation of underwater adhesives using low-cost procyanidins （PA） extracted from grape seed and commercial polyethylene glycol oligomers （PEG） as building blocks， and realize the formation of biomimetic adhesives initiated by hydrogen bonding interaction. The adhesive can adhere to different substrates in both air and underwater， and can be reused at least three times. In addition， the PA/PEG adhesives are easy to prepare， have good antibacterial activity and biocompatibility. The PA/PEG adhesives could be widely used for pharmaceutical applications due to simple preparation， reusability， broad spectrum adhesion and antibacterial activity.

Key words: Hydrogen bond, Procyanidin, Adhesive, Antibacterial activity

CLC Number:

O648.1

Xiao-Ming XIE, Jia-Qi ZHANG. Hydrogen Bond Interaction Driven Procyanidine Assembly into Underwater Adhesive with Antibacterial Activity[J]. Chinese Journal of Applied Chemistry, 2022, 39(10): 1533-1542.

Figures/Tables 9

Fig.1 Chemical structures of （A） PA and （B） PEG800，（C） the packing model of PA/PEG800 adhesive

Fig.2 Digital images of complex formed from （A） the co-assembly of PA and PEG800，（B） PA/PEG1000，（C） PA/PEG600，（D） CA/PEG800 and （E） TA/PEG800

Fig.3 （A） SEM image of the PA/PEG800 adhesive；（B） Rheological behavior of the PA/PEG800 adhesive；（C） Digital images of PA/PEG800 adhesive on air adhesion for different materials including wood， rubber， PEEK， PE， caenelian， PTFE， glass， SS， Titanium；（D） Underwater adhesion for different materials including PTFE， SS， PP， PEEK and Titanium

Fig.4 Photographs of PA/PEG800 adhesive in aqueous solution with different aging times

Fig.5 （A） Underwater shear adhesion strengths of the PA/PEG800 adhesive bonded to different substrates （PEEK， PP， PC， SS）；（B） underwater shear strengths of PA/PEG800 adhesive along with the attachment/detachment cycles （obtained from SS substrates）；（C） dynamic rheology behavior over time after the adhesive was broken by applying a 200% strain amplitude sweep；（D） FT-IR spectra of PA， PEG800 and PA/PEG800 complex in the range of 4000 ~ 400 cm-1

Fig.6 （A） 1H NMR spectra of PA， PEG800 and PA/PEG800 adhesive；（B） underwater shear strengths of PA/PEG1000， PA/MPEG1000 and PA/MdPEG1000 adhesive （obtained from SS substrates）；（C） digital images of complex formed from the co-assembly of PA and PVA；（D） the bacterial colonies calculated by a colony count method after the E.coli cells are treated with PA， PEG800 and PA/PEG800

Fig.7 The kill ratio of PA/PEG800 with different concentration for （A） E.coli and （B） S.aureus cells， the inhibitory effect of PA/PEG800 adhesive for （C） E.coli and （D） S.aureus cells on agar plates

Fig.8 SEM images of the E.coli and S.aureus cells before （A， C） and after （B， D） being treated with PA/PEG800 adhesive

Fig.9 （A） Histogram of cell survival rates of PA， PEG800， PA/PEG800 on L-929 cells； flow cytometry of the effects of （B） the blank and （C） PA/PEG800 samples on L-929 cells；（D） LSCM images of L-929 cells with PA/PEG800 following different incubation times

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Hydrogen Bond Interaction Driven Procyanidine Assembly into Underwater Adhesive with Antibacterial Activity

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