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A Combinatorial
Approach to the Design of Boronate
Ester Hydrogels Reveals the Remarkable Binding Properties of a Bicyclic
Diol
Léa Terriac (19017333)
Khaled Alsabil (11153964)
Garance Saint-Pé (24902530)
Guillaume Viault (5536127)
Yves Maugars (11612960)
Catherine Garnier (3686524)
Jean-Jacques Helesbeux (2130412)
Vianney Delplace (1356408)
Biophysics
Biochemistry
Space Science
Physical Sciences not elsewhere classified
Genetics
Pharmacology
Biotechnology
Chemical Sciences not elsewhere classified
Biological Sciences not elsewhere classified
Cancer
Computational Biology
using hyaluronic acid
two hydroxyl groups
relaxing viscoelastic liquids
dynamic covalent reactions
behave like fast
3d cell culture
rigid bicyclic structure
optimal diol structure
viscoelastic hydrogel design
various biomedical applications
physiological ph due
</ sub >)
remarkable binding properties
crosslinking pairs based
remarkable properties
bridged bicyclic
biomedical field
binding strength
applications ranging
>< sub
>- diol
k </
cis </
unique ability
study revealed
specific three
relative bioorthogonality
reach values
previous systems
fold greater
drug delivery
dimensional orientation
deeper understanding
combinatorial screening
combinatorial approach
boronate ester
base polymer
Viscoelastic hydrogels are increasingly being used in
the biomedical
field, with applications ranging from 3D cell culture to drug delivery.
Boronate ester (BE) formation is one of the dynamic covalent reactions
that can be used for viscoelastic hydrogel design. BE formation stands
out for the stability and relative bioorthogonality of its precursors,
i.e., phenylboronic acids and diols. However, BE hydrogels usually
lack stability, are soft, and behave like fast-relaxing viscoelastic
liquids at physiological pH due to low BE binding strength. To address
these limitations, we performed a combinatorial screening of BE crosslinking
pairs based on PBAs and cyclic <i>cis</i>-diols, using hyaluronic
acid as a base polymer. Our study revealed the unique ability of norbodiol,
a bridged bicyclic <i>cis</i>-diol, to form BE hydrogels
with all the PBAs tested. We demonstrated that this is due to norbodiol’s
exceptional association constants (<i>K</i><sub>a</sub>)
with PBAs, which can reach values of up to 6600 M<sup>–1</sup>. Compared to a list of other diols, we further showed that the remarkable
properties of norbodiol could be explained by its rigid bicyclic structure
and the specific three-dimensional orientation of its two hydroxyl
groups. These findings provide initial insights toward a deeper understanding
of the optimal diol structure for BE formation and stability. Norbodiol-based
BE crosslinking produced hydrogels whose relaxation properties were
20- to 200-fold greater than those of previous systems. We further
optimized two hydrogel formulations with single or dual BE crosslinking
for use in various biomedical applications, highlighting the potential
of our discovery.
2026-09-14T00:00:00Z
Dataset
Media
10.1021/acs.chemmater.6c01255.s001
https://figshare.com/articles/media/A_Combinatorial_Approach_to_the_Design_of_Boronate_Ester_Hydrogels_Reveals_the_Remarkable_Binding_Properties_of_a_Bicyclic_Diol/33759271
CC BY-NC 4.0