Synthesis of PEG hydrogel with dityrosine for multi-functionality and pH-dependent fluorescence

Jee Yun Choi, Dong Ik Lee, Chan Jin Kim, Chang-Ha Lee, Ik Sung Ahn

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A poly(ethylene glycol) (PEG)-based hydrogel was synthesized by the copolymerization of PEG diacrylate (PEGDA) and PEG methacrylate (PEGMA) linked with N,. N'-di(tert-butoxycarbonyl)-dityrosine (DBDY). Owing to the presence of the dityrosine derivative DBDY, the resulting hydrogel exhibited pH-dependent fluorescence and contained multi-functional groups (1 carboxylic acid group and 2 amine groups protected by tert-butoxycarbonyl groups). A high molecular mass chemical can be bound to DBDY in the hydrogel through one of these functional groups (i.e. the formation of amide bonding). Then the porosity of the resulting hydrogel is increased by the action of an enzyme such as proteinase. Also, if a drug is bound directly to DBDY, the enzyme can control its detachment. Hence, the PEGMA-DBDY hydrogel could be useful for drug release near the site of the disease where the expression level of a certain enzyme is especially high (e.g. matrix metalloproteinases in cancers). Binding of a UV-absorbing compound to DBDY was monitored by measuring the change in fluorescence intensity, which is known as the phenomenon of fluorescence resonance energy transfer (FRET).

Original languageEnglish
Pages (from-to)611-616
Number of pages6
JournalJournal of Industrial and Engineering Chemistry
Volume18
Issue number2
DOIs
Publication statusPublished - 2012 Mar 25

Fingerprint

Hydrogel
Hydrogels
Polyethylene glycols
Fluorescence
Enzymes
Functional groups
Methacrylates
Molecular mass
Carboxylic acids
Amides
Copolymerization
Amines
Porosity
Carboxylic Acids
dityrosine
Matrix Metalloproteinases
Pharmaceutical Preparations
Derivatives
Peptide Hydrolases

All Science Journal Classification (ASJC) codes

  • Chemical Engineering(all)

Cite this

@article{d5875482b81a4b46bbdf8729c975f380,
title = "Synthesis of PEG hydrogel with dityrosine for multi-functionality and pH-dependent fluorescence",
abstract = "A poly(ethylene glycol) (PEG)-based hydrogel was synthesized by the copolymerization of PEG diacrylate (PEGDA) and PEG methacrylate (PEGMA) linked with N,. N'-di(tert-butoxycarbonyl)-dityrosine (DBDY). Owing to the presence of the dityrosine derivative DBDY, the resulting hydrogel exhibited pH-dependent fluorescence and contained multi-functional groups (1 carboxylic acid group and 2 amine groups protected by tert-butoxycarbonyl groups). A high molecular mass chemical can be bound to DBDY in the hydrogel through one of these functional groups (i.e. the formation of amide bonding). Then the porosity of the resulting hydrogel is increased by the action of an enzyme such as proteinase. Also, if a drug is bound directly to DBDY, the enzyme can control its detachment. Hence, the PEGMA-DBDY hydrogel could be useful for drug release near the site of the disease where the expression level of a certain enzyme is especially high (e.g. matrix metalloproteinases in cancers). Binding of a UV-absorbing compound to DBDY was monitored by measuring the change in fluorescence intensity, which is known as the phenomenon of fluorescence resonance energy transfer (FRET).",
author = "Choi, {Jee Yun} and Lee, {Dong Ik} and Kim, {Chan Jin} and Chang-Ha Lee and Ahn, {Ik Sung}",
year = "2012",
month = "3",
day = "25",
doi = "10.1016/j.jiec.2011.11.052",
language = "English",
volume = "18",
pages = "611--616",
journal = "Journal of Industrial and Engineering Chemistry",
issn = "1226-086X",
publisher = "Korean Society of Industrial Engineering Chemistry",
number = "2",

}

Synthesis of PEG hydrogel with dityrosine for multi-functionality and pH-dependent fluorescence. / Choi, Jee Yun; Lee, Dong Ik; Kim, Chan Jin; Lee, Chang-Ha; Ahn, Ik Sung.

In: Journal of Industrial and Engineering Chemistry, Vol. 18, No. 2, 25.03.2012, p. 611-616.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of PEG hydrogel with dityrosine for multi-functionality and pH-dependent fluorescence

AU - Choi, Jee Yun

AU - Lee, Dong Ik

AU - Kim, Chan Jin

AU - Lee, Chang-Ha

AU - Ahn, Ik Sung

PY - 2012/3/25

Y1 - 2012/3/25

N2 - A poly(ethylene glycol) (PEG)-based hydrogel was synthesized by the copolymerization of PEG diacrylate (PEGDA) and PEG methacrylate (PEGMA) linked with N,. N'-di(tert-butoxycarbonyl)-dityrosine (DBDY). Owing to the presence of the dityrosine derivative DBDY, the resulting hydrogel exhibited pH-dependent fluorescence and contained multi-functional groups (1 carboxylic acid group and 2 amine groups protected by tert-butoxycarbonyl groups). A high molecular mass chemical can be bound to DBDY in the hydrogel through one of these functional groups (i.e. the formation of amide bonding). Then the porosity of the resulting hydrogel is increased by the action of an enzyme such as proteinase. Also, if a drug is bound directly to DBDY, the enzyme can control its detachment. Hence, the PEGMA-DBDY hydrogel could be useful for drug release near the site of the disease where the expression level of a certain enzyme is especially high (e.g. matrix metalloproteinases in cancers). Binding of a UV-absorbing compound to DBDY was monitored by measuring the change in fluorescence intensity, which is known as the phenomenon of fluorescence resonance energy transfer (FRET).

AB - A poly(ethylene glycol) (PEG)-based hydrogel was synthesized by the copolymerization of PEG diacrylate (PEGDA) and PEG methacrylate (PEGMA) linked with N,. N'-di(tert-butoxycarbonyl)-dityrosine (DBDY). Owing to the presence of the dityrosine derivative DBDY, the resulting hydrogel exhibited pH-dependent fluorescence and contained multi-functional groups (1 carboxylic acid group and 2 amine groups protected by tert-butoxycarbonyl groups). A high molecular mass chemical can be bound to DBDY in the hydrogel through one of these functional groups (i.e. the formation of amide bonding). Then the porosity of the resulting hydrogel is increased by the action of an enzyme such as proteinase. Also, if a drug is bound directly to DBDY, the enzyme can control its detachment. Hence, the PEGMA-DBDY hydrogel could be useful for drug release near the site of the disease where the expression level of a certain enzyme is especially high (e.g. matrix metalloproteinases in cancers). Binding of a UV-absorbing compound to DBDY was monitored by measuring the change in fluorescence intensity, which is known as the phenomenon of fluorescence resonance energy transfer (FRET).

UR - http://www.scopus.com/inward/record.url?scp=84862832478&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862832478&partnerID=8YFLogxK

U2 - 10.1016/j.jiec.2011.11.052

DO - 10.1016/j.jiec.2011.11.052

M3 - Article

AN - SCOPUS:84862832478

VL - 18

SP - 611

EP - 616

JO - Journal of Industrial and Engineering Chemistry

JF - Journal of Industrial and Engineering Chemistry

SN - 1226-086X

IS - 2

ER -