Synthesis of biomembrane-mimic polymers with various phospholipid head groups

Heejin Kim, Wonmin Choi, Seonju Lee, Sooyeol Kim, Jiyeon Ham, Ji-Hun Seo, Sangmok Jang, Yan Lee

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2- methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3-[4,5-dimethylthiazol-2-yl]-2,5- diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants.

Original languageEnglish
Pages (from-to)517-524
Number of pages8
JournalPolymer
Volume55
Issue number2
DOIs
Publication statusPublished - 2014 Jan 30
Externally publishedYes

Fingerprint

Phosphatidic Acids
Phosphatidylserines
Phospholipids
Phosphoserine
Polymers
Monomers
Phosphoric acid
Acids
Tissue
Ethanolamines
Ethanolamine
Lipid bilayers
Atom transfer radical polymerization
Gel permeation chromatography
Molecular weight distribution
Cytotoxicity
Phosphatidylcholines
L-Lactate Dehydrogenase
Tissue engineering
Serine

Keywords

  • Biomembrane-mimic polymers
  • Cytocompatibility
  • Phospholipid head groups

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Synthesis of biomembrane-mimic polymers with various phospholipid head groups. / Kim, Heejin; Choi, Wonmin; Lee, Seonju; Kim, Sooyeol; Ham, Jiyeon; Seo, Ji-Hun; Jang, Sangmok; Lee, Yan.

In: Polymer, Vol. 55, No. 2, 30.01.2014, p. 517-524.

Research output: Contribution to journalArticle

Kim, H, Choi, W, Lee, S, Kim, S, Ham, J, Seo, J-H, Jang, S & Lee, Y 2014, 'Synthesis of biomembrane-mimic polymers with various phospholipid head groups', Polymer, vol. 55, no. 2, pp. 517-524. https://doi.org/10.1016/j.polymer.2013.12.020
Kim, Heejin ; Choi, Wonmin ; Lee, Seonju ; Kim, Sooyeol ; Ham, Jiyeon ; Seo, Ji-Hun ; Jang, Sangmok ; Lee, Yan. / Synthesis of biomembrane-mimic polymers with various phospholipid head groups. In: Polymer. 2014 ; Vol. 55, No. 2. pp. 517-524.
@article{d4328908188041f39f76f6e64568a389,
title = "Synthesis of biomembrane-mimic polymers with various phospholipid head groups",
abstract = "Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2- methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3-[4,5-dimethylthiazol-2-yl]-2,5- diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants.",
keywords = "Biomembrane-mimic polymers, Cytocompatibility, Phospholipid head groups",
author = "Heejin Kim and Wonmin Choi and Seonju Lee and Sooyeol Kim and Jiyeon Ham and Ji-Hun Seo and Sangmok Jang and Yan Lee",
year = "2014",
month = "1",
day = "30",
doi = "10.1016/j.polymer.2013.12.020",
language = "English",
volume = "55",
pages = "517--524",
journal = "Polymer (United Kingdom)",
issn = "0032-3861",
publisher = "Elsevier BV",
number = "2",

}

TY - JOUR

T1 - Synthesis of biomembrane-mimic polymers with various phospholipid head groups

AU - Kim, Heejin

AU - Choi, Wonmin

AU - Lee, Seonju

AU - Kim, Sooyeol

AU - Ham, Jiyeon

AU - Seo, Ji-Hun

AU - Jang, Sangmok

AU - Lee, Yan

PY - 2014/1/30

Y1 - 2014/1/30

N2 - Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2- methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3-[4,5-dimethylthiazol-2-yl]-2,5- diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants.

AB - Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2- methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3-[4,5-dimethylthiazol-2-yl]-2,5- diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants.

KW - Biomembrane-mimic polymers

KW - Cytocompatibility

KW - Phospholipid head groups

UR - http://www.scopus.com/inward/record.url?scp=84892791941&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84892791941&partnerID=8YFLogxK

U2 - 10.1016/j.polymer.2013.12.020

DO - 10.1016/j.polymer.2013.12.020

M3 - Article

AN - SCOPUS:84892791941

VL - 55

SP - 517

EP - 524

JO - Polymer (United Kingdom)

JF - Polymer (United Kingdom)

SN - 0032-3861

IS - 2

ER -