Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification
The structural characteristic of oxidized poly (2-hydroxyethyl acrylate) (OP) was confirmed by high-performance liquid chromatography, gel permeation chromatography and hydroxylamine hydrochloride titration. The results demonstrated that OP prepared through 2,2,6,6-tetramethylpiperidine-1-oxyl-media...
Main Authors: | , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
The Royal Society
2021-02-01
|
Series: | Royal Society Open Science |
Subjects: | |
Online Access: | https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.201892 |
id |
doaj-da87a7b5d11e4eb089579733e341e5cd |
---|---|
record_format |
Article |
spelling |
doaj-da87a7b5d11e4eb089579733e341e5cd2021-03-15T15:27:04ZengThe Royal SocietyRoyal Society Open Science2054-57032021-02-018210.1098/rsos.201892201892Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modificationBaohua LiuJian WangLili JiTing BaiYin ZhangDayu LiuThe structural characteristic of oxidized poly (2-hydroxyethyl acrylate) (OP) was confirmed by high-performance liquid chromatography, gel permeation chromatography and hydroxylamine hydrochloride titration. The results demonstrated that OP prepared through 2,2,6,6-tetramethylpiperidine-1-oxyl-mediated oxidation of poly (2-hydroxyethyl acrylate) was featured by multiple aldehyde groups on its side chain, with no free formaldehyde produced during the oxidation process. The computational simulation for the electrophilic reactivity of OP molecule showed that the reactivity of the aldehyde groups in OP with the amino groups of collagen was comparable to that of glutaraldehyde. In this study, OP was chosen as a collagen modifier to investigate the modification effects on the secondary structure, aggregation behaviour and thermal stability of collagen. The covalent cross-linking occurred between the aldehyde groups of OP and the amino groups of collagen under alkaline condition. The covalent binding between OP and collagen was strengthened with the increasing reaction pH and OP dosage, and the triple helix of collagen was altered to some degree. Furthermore, OP promoted the intense aggregation of collagen and enhanced the thermal stability of collagen. This work provides guidance for preparing novel collagen modifier with multiple aldehyde groups.https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.201892poly (2-hydroxyethyl acrylate)hydroxyl oxidationaldehyde groupcollagencross-linkingmodification |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Baohua Liu Jian Wang Lili Ji Ting Bai Yin Zhang Dayu Liu |
spellingShingle |
Baohua Liu Jian Wang Lili Ji Ting Bai Yin Zhang Dayu Liu Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification Royal Society Open Science poly (2-hydroxyethyl acrylate) hydroxyl oxidation aldehyde group collagen cross-linking modification |
author_facet |
Baohua Liu Jian Wang Lili Ji Ting Bai Yin Zhang Dayu Liu |
author_sort |
Baohua Liu |
title |
Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification |
title_short |
Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification |
title_full |
Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification |
title_fullStr |
Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification |
title_full_unstemmed |
Structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification |
title_sort |
structure validation of oxidized poly (2-hydroxyethyl acrylate) with multiple aldehyde groups and its application for collagen modification |
publisher |
The Royal Society |
series |
Royal Society Open Science |
issn |
2054-5703 |
publishDate |
2021-02-01 |
description |
The structural characteristic of oxidized poly (2-hydroxyethyl acrylate) (OP) was confirmed by high-performance liquid chromatography, gel permeation chromatography and hydroxylamine hydrochloride titration. The results demonstrated that OP prepared through 2,2,6,6-tetramethylpiperidine-1-oxyl-mediated oxidation of poly (2-hydroxyethyl acrylate) was featured by multiple aldehyde groups on its side chain, with no free formaldehyde produced during the oxidation process. The computational simulation for the electrophilic reactivity of OP molecule showed that the reactivity of the aldehyde groups in OP with the amino groups of collagen was comparable to that of glutaraldehyde. In this study, OP was chosen as a collagen modifier to investigate the modification effects on the secondary structure, aggregation behaviour and thermal stability of collagen. The covalent cross-linking occurred between the aldehyde groups of OP and the amino groups of collagen under alkaline condition. The covalent binding between OP and collagen was strengthened with the increasing reaction pH and OP dosage, and the triple helix of collagen was altered to some degree. Furthermore, OP promoted the intense aggregation of collagen and enhanced the thermal stability of collagen. This work provides guidance for preparing novel collagen modifier with multiple aldehyde groups. |
topic |
poly (2-hydroxyethyl acrylate) hydroxyl oxidation aldehyde group collagen cross-linking modification |
url |
https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.201892 |
work_keys_str_mv |
AT baohualiu structurevalidationofoxidizedpoly2hydroxyethylacrylatewithmultiplealdehydegroupsanditsapplicationforcollagenmodification AT jianwang structurevalidationofoxidizedpoly2hydroxyethylacrylatewithmultiplealdehydegroupsanditsapplicationforcollagenmodification AT liliji structurevalidationofoxidizedpoly2hydroxyethylacrylatewithmultiplealdehydegroupsanditsapplicationforcollagenmodification AT tingbai structurevalidationofoxidizedpoly2hydroxyethylacrylatewithmultiplealdehydegroupsanditsapplicationforcollagenmodification AT yinzhang structurevalidationofoxidizedpoly2hydroxyethylacrylatewithmultiplealdehydegroupsanditsapplicationforcollagenmodification AT dayuliu structurevalidationofoxidizedpoly2hydroxyethylacrylatewithmultiplealdehydegroupsanditsapplicationforcollagenmodification |
_version_ |
1724220567759880192 |