Modified hyaluronic acid with enhanced resistance to degradation

Modified hyaluronic acid with enhanced resistance to degradation

A mild and efficient reduction of negatively charged glucuronate units of hyaluronic acid (HA) into less polar glucose units has not been reported yet. However, this modification could significantly affect physical and chemical properties. Here we show a one-pot procedure where HA is converted into...

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Bibliographic Details
Published in:Carbohydrate polymers Vol. 320; p. 121241
Main Authors: Buffa, Radovan, Klejch, Tomáš, Hermannová, Martina, Hejlová, Lenka, Svozil, Vít, Vágnerová, Hana, Škubalová, Hana, Nešporová, Kristina, Velebný, Vladimír
Format: Journal Article
Language:English
Published: Elsevier Ltd 15-11-2023
Subjects:
Biocompatibility
Degradation
Hyaluronan
Polarity
Reduction
Stability
AcOH
PRG
TCT
DMSO
EDC
Mw
COSY
DS
Degradation
Hyaluronan
Reduction
V
DMA
Polarity
Biocompatibility
BOH
GlcNAc
dHA2
tR
GlcA
Stability
MS
h
DMTMM
DIO
SEC-MALLS
m
NMM
NMR
t
δ
ETG
HA
FA
IPA
HSQC
GLC
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Summary:A mild and efficient reduction of negatively charged glucuronate units of hyaluronic acid (HA) into less polar glucose units has not been reported yet. However, this modification could significantly affect physical and chemical properties. Here we show a one-pot procedure where HA is converted into its derivate with carboxyl groups reduced to primary alcohols (HA-Red) without severe polymer degradation. Optimized synthesis aimed at aqueous solutions allowed the preparation of polysaccharides with molecular weights up to 1000 kDa. The chemical structure of HA-Red was proved by 2-dimensional NMR methodologies, FT-IR, LC-MS and SECMALLS. The final materials were exposed to a higher temperature or digested with bovine testicular hyaluronidase (BTH). Obtained data proved higher stability of HA-Red compared to HA, and significant dependence of stability on the degree of modification was observed in most cases. Preliminary in vitro studies showed no negative effects of HA-Red on the growth of 3T3 fibroblasts, which may be promising for applications requiring biodegradable and biocompatible HA derivatives with increased resistance to degradation. [Display omitted]
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ISSN:0144-8617
1879-1344
DOI:10.1016/j.carbpol.2023.121241