A self-destroying polycationic polymer: Biodegradable poly(4-hydroxy-L- proline ester)

Yong-beom Lim, Young Hun Choi, Jong Sang Park

Research output: Contribution to journalArticle

168 Citations (Scopus)

Abstract

A self-destroying, biodegradable, and polycationic polyester, poly(trans-4-hydroxy-L-proline ester) (PHP ester), was synthesized, and the interaction of the polymer with polyanion DNA was investigated. Degradation of the polymer in aqueous solution was investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and by measuring the pH change as carboxylic acids are formed as products of the degradation of the polymer backbone ester bond. It was shown from MALDI-MS data that the polymer degraded to less than half of the intact polymer molecular weight in less than 2 h. But a slower degradation rate after initial rapid degradation (within 1 day) was apparent. A self-destroying mechanism at the initial stage is proposed. The polymer was gradually degraded to near completion in 3 months in an aqueous solution to monomer, hydroxyproline, a major constituent of collagen, which could easily be detected by using MALDI-MS. Although the polymer degraded very quickly in an aqueous solution, it formed stable PHP ester/DNA complexes by electrostatic interaction when the polymer was mixed with the polyanionic DNA solution. The condensation behavior of DNA with the polymer to form self-assembled PHP ester/DNA complexes was characterized by electrophoretic mobility shift assay, dynamic light scattering, ζ potential, and nuclease resistance assay. These results show that PHP ester forms a strong complex with DNA by means of electrostatic interaction. Transfection of β-galactosidase gene into mammalian cell using PHP ester/DNA complexes was successful, showing the possibility of using PHP ester as a biodegradable gene delivery carrier.

Original languageEnglish
Pages (from-to)5633-5639
Number of pages7
JournalJournal of the American Chemical Society
Volume121
Issue number24
DOIs
Publication statusPublished - 1999 Jun 23

Fingerprint

Biodegradable polymers
Proline
Hydroxyproline
Esters
Polymers
DNA
Degradation
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Coulomb interactions
Static Electricity
Assays
Genes
Galactosidases
Electrophoretic mobility
Polyesters
Electrophoretic Mobility Shift Assay
Dynamic light scattering
Carboxylic Acids
Carboxylic acids
Collagen

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

@article{f2fdf0b97076409da50355fa2299918c,
title = "A self-destroying polycationic polymer: Biodegradable poly(4-hydroxy-L- proline ester)",
abstract = "A self-destroying, biodegradable, and polycationic polyester, poly(trans-4-hydroxy-L-proline ester) (PHP ester), was synthesized, and the interaction of the polymer with polyanion DNA was investigated. Degradation of the polymer in aqueous solution was investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and by measuring the pH change as carboxylic acids are formed as products of the degradation of the polymer backbone ester bond. It was shown from MALDI-MS data that the polymer degraded to less than half of the intact polymer molecular weight in less than 2 h. But a slower degradation rate after initial rapid degradation (within 1 day) was apparent. A self-destroying mechanism at the initial stage is proposed. The polymer was gradually degraded to near completion in 3 months in an aqueous solution to monomer, hydroxyproline, a major constituent of collagen, which could easily be detected by using MALDI-MS. Although the polymer degraded very quickly in an aqueous solution, it formed stable PHP ester/DNA complexes by electrostatic interaction when the polymer was mixed with the polyanionic DNA solution. The condensation behavior of DNA with the polymer to form self-assembled PHP ester/DNA complexes was characterized by electrophoretic mobility shift assay, dynamic light scattering, ζ potential, and nuclease resistance assay. These results show that PHP ester forms a strong complex with DNA by means of electrostatic interaction. Transfection of β-galactosidase gene into mammalian cell using PHP ester/DNA complexes was successful, showing the possibility of using PHP ester as a biodegradable gene delivery carrier.",
author = "Yong-beom Lim and Choi, {Young Hun} and Park, {Jong Sang}",
year = "1999",
month = "6",
day = "23",
doi = "10.1021/ja984012k",
language = "English",
volume = "121",
pages = "5633--5639",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "24",

}

A self-destroying polycationic polymer : Biodegradable poly(4-hydroxy-L- proline ester). / Lim, Yong-beom; Choi, Young Hun; Park, Jong Sang.

In: Journal of the American Chemical Society, Vol. 121, No. 24, 23.06.1999, p. 5633-5639.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A self-destroying polycationic polymer

T2 - Biodegradable poly(4-hydroxy-L- proline ester)

AU - Lim, Yong-beom

AU - Choi, Young Hun

AU - Park, Jong Sang

PY - 1999/6/23

Y1 - 1999/6/23

N2 - A self-destroying, biodegradable, and polycationic polyester, poly(trans-4-hydroxy-L-proline ester) (PHP ester), was synthesized, and the interaction of the polymer with polyanion DNA was investigated. Degradation of the polymer in aqueous solution was investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and by measuring the pH change as carboxylic acids are formed as products of the degradation of the polymer backbone ester bond. It was shown from MALDI-MS data that the polymer degraded to less than half of the intact polymer molecular weight in less than 2 h. But a slower degradation rate after initial rapid degradation (within 1 day) was apparent. A self-destroying mechanism at the initial stage is proposed. The polymer was gradually degraded to near completion in 3 months in an aqueous solution to monomer, hydroxyproline, a major constituent of collagen, which could easily be detected by using MALDI-MS. Although the polymer degraded very quickly in an aqueous solution, it formed stable PHP ester/DNA complexes by electrostatic interaction when the polymer was mixed with the polyanionic DNA solution. The condensation behavior of DNA with the polymer to form self-assembled PHP ester/DNA complexes was characterized by electrophoretic mobility shift assay, dynamic light scattering, ζ potential, and nuclease resistance assay. These results show that PHP ester forms a strong complex with DNA by means of electrostatic interaction. Transfection of β-galactosidase gene into mammalian cell using PHP ester/DNA complexes was successful, showing the possibility of using PHP ester as a biodegradable gene delivery carrier.

AB - A self-destroying, biodegradable, and polycationic polyester, poly(trans-4-hydroxy-L-proline ester) (PHP ester), was synthesized, and the interaction of the polymer with polyanion DNA was investigated. Degradation of the polymer in aqueous solution was investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and by measuring the pH change as carboxylic acids are formed as products of the degradation of the polymer backbone ester bond. It was shown from MALDI-MS data that the polymer degraded to less than half of the intact polymer molecular weight in less than 2 h. But a slower degradation rate after initial rapid degradation (within 1 day) was apparent. A self-destroying mechanism at the initial stage is proposed. The polymer was gradually degraded to near completion in 3 months in an aqueous solution to monomer, hydroxyproline, a major constituent of collagen, which could easily be detected by using MALDI-MS. Although the polymer degraded very quickly in an aqueous solution, it formed stable PHP ester/DNA complexes by electrostatic interaction when the polymer was mixed with the polyanionic DNA solution. The condensation behavior of DNA with the polymer to form self-assembled PHP ester/DNA complexes was characterized by electrophoretic mobility shift assay, dynamic light scattering, ζ potential, and nuclease resistance assay. These results show that PHP ester forms a strong complex with DNA by means of electrostatic interaction. Transfection of β-galactosidase gene into mammalian cell using PHP ester/DNA complexes was successful, showing the possibility of using PHP ester as a biodegradable gene delivery carrier.

UR - http://www.scopus.com/inward/record.url?scp=0042416911&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042416911&partnerID=8YFLogxK

U2 - 10.1021/ja984012k

DO - 10.1021/ja984012k

M3 - Article

AN - SCOPUS:0042416911

VL - 121

SP - 5633

EP - 5639

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 24

ER -