Injectable dynamic covalent hydrogels of boronic acid polymers cross-linked by bioactive plant-derived polyphenols

Huang, Zhuojun; Delparastan, Peyman; Burch, Patrick; Cheng, Jing; Cao, Yi; Messersmith, Phillip B.

doi:10.1039/c8bm00453f

Injectable dynamic covalent hydrogels of boronic acid polymers cross-linked by bioactive plant-derived polyphenols

Journal Article · Thu Aug 02 00:00:00 EDT 2018 · Biomaterials Science

DOI:https://doi.org/10.1039/c8bm00453f· OSTI ID:1624955

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Univ. of California, Berkeley, CA (United States); University of California, Berkeley
Univ. of California, Berkeley, CA (United States)
Nanjing Univ. (China)
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

We report here the development of hydrogels formed at physiological conditions using PEG (polyethylene glycol) based polymers modified with boronic acids (BAs) as backbones and the plant derived polyphenols ellagic acid (EA), epigallocatechin gallate (EGCG), tannic acid (TA), nordihydroguaiaretic acid (NDGA), rutin trihydrate (RT), rosmarinic acid (RA) and carminic acid (CA) as linkers. Rheological frequency sweep and single molecule force spectroscopy (SMFS) experiments show that hydrogels linked with EGCG and TA are mechanically stiff, arising from the dynamic covalent bond formed by the polyphenol linker and boronic acid functionalized polymer. Stability tests of the hydrogels in physiological conditions revealed that gels linked with EA, EGCG, and TA are stable. We furthermore showed that EA- and EGCG-linked hydrogels can be formed via in situ gelation in pH 7.4 buffer, and provide long-term steady state release of bioactive EA. In vitro experiments showed that EA-linked hydrogel significantly reduced the viability of CAL-27 human oral cancer cells via gradual release of EA.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Lab (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: National Institutes of Health (NIH); National Natural Science Foundation of China (NNSFC); Swiss National Science Foundation (SNSF); USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1624955

Journal Information:: Biomaterials Science, Journal Name: Biomaterials Science Journal Issue: 9 Vol. 6; ISSN 2047-4830

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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