Chemical immobilization of retinoic acid within poly(ε-caprolactone) nanoparticles based on drug-polymer bioconjugates

Yoon Sung Nam; Kil Joong Kim; Hyung Seok Kang; Tae Gwan Park; Sang Hoon Han; Ih Seop Chang

doi:10.1002/app.12366

Chemical immobilization of retinoic acid within poly(ε-caprolactone) nanoparticles based on drug-polymer bioconjugates

Yoon Sung Nam, Kil Joong Kim, Hyung Seok Kang, Tae Gwan Park, Sang Hoon Han, Ih Seop Chang

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

All-trans-retinoic acid (RA) was chemically conjugated to biodegradable poly(ε-caprolactone) (PCL₁₀; number-average M_w ≈ 1250) via an ester linkage. The conjugation was carried out using N,N-dicyclohexylcarbodiimide and 4-dimethyl aminopyridine as a coupling agent. The molar ratio of the drug to the polymer was 1.11 as determined by ¹H-NMR analysis. DSC and WAXD results showed that the formation of crystalline structures of RA was effectively suppressed by conjugation with PCL. The RA-PCL conjugates were formulated into nanoparticles by a spontaneous phase-inversion technique. Morphological characteristics of the resultant nanoparticles and drug-loading efficiencies were compared with those of free RA-loaded nanoparticles. The drug-loading efficiency of RA-PCL conjugates was almost 100%, while that of free RA was only ∼12%. The majority of unconjugated RA was found to form undesirable free-drug crystals out of nanoparticles, as observed by TEM analysis. This study demonstrates that the conjugation approach of RA to PCL can be an effective means to Immobilize and encapsulate RA within nanoparticles for pharmaceutical applications.

Original language	English
Pages (from-to)	1631-1637
Number of pages	7
Journal	Journal of Applied Polymer Science
Volume	89
Issue number	6
DOIs	https://doi.org/10.1002/app.12366
State	Published - Aug 8 2003
Externally published	Yes

Keywords

Biodegradable
Biological applications of polymers
Conjugated polymers
Nanotechnology
Polyesters

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title = "Chemical immobilization of retinoic acid within poly(ε-caprolactone) nanoparticles based on drug-polymer bioconjugates",

abstract = "All-trans-retinoic acid (RA) was chemically conjugated to biodegradable poly(ε-caprolactone) (PCL10; number-average Mw ≈ 1250) via an ester linkage. The conjugation was carried out using N,N-dicyclohexylcarbodiimide and 4-dimethyl aminopyridine as a coupling agent. The molar ratio of the drug to the polymer was 1.11 as determined by 1H-NMR analysis. DSC and WAXD results showed that the formation of crystalline structures of RA was effectively suppressed by conjugation with PCL. The RA-PCL conjugates were formulated into nanoparticles by a spontaneous phase-inversion technique. Morphological characteristics of the resultant nanoparticles and drug-loading efficiencies were compared with those of free RA-loaded nanoparticles. The drug-loading efficiency of RA-PCL conjugates was almost 100%, while that of free RA was only ∼12%. The majority of unconjugated RA was found to form undesirable free-drug crystals out of nanoparticles, as observed by TEM analysis. This study demonstrates that the conjugation approach of RA to PCL can be an effective means to Immobilize and encapsulate RA within nanoparticles for pharmaceutical applications.",

keywords = "Biodegradable, Biological applications of polymers, Conjugated polymers, Nanotechnology, Polyesters",

author = "Nam, {Yoon Sung} and Kim, {Kil Joong} and Kang, {Hyung Seok} and Park, {Tae Gwan} and Han, {Sang Hoon} and Chang, {Ih Seop}",

year = "2003",

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doi = "10.1002/app.12366",

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AU - Nam, Yoon Sung

AU - Kim, Kil Joong

AU - Kang, Hyung Seok

AU - Park, Tae Gwan

AU - Han, Sang Hoon

AU - Chang, Ih Seop

PY - 2003/8/8

Y1 - 2003/8/8

N2 - All-trans-retinoic acid (RA) was chemically conjugated to biodegradable poly(ε-caprolactone) (PCL10; number-average Mw ≈ 1250) via an ester linkage. The conjugation was carried out using N,N-dicyclohexylcarbodiimide and 4-dimethyl aminopyridine as a coupling agent. The molar ratio of the drug to the polymer was 1.11 as determined by 1H-NMR analysis. DSC and WAXD results showed that the formation of crystalline structures of RA was effectively suppressed by conjugation with PCL. The RA-PCL conjugates were formulated into nanoparticles by a spontaneous phase-inversion technique. Morphological characteristics of the resultant nanoparticles and drug-loading efficiencies were compared with those of free RA-loaded nanoparticles. The drug-loading efficiency of RA-PCL conjugates was almost 100%, while that of free RA was only ∼12%. The majority of unconjugated RA was found to form undesirable free-drug crystals out of nanoparticles, as observed by TEM analysis. This study demonstrates that the conjugation approach of RA to PCL can be an effective means to Immobilize and encapsulate RA within nanoparticles for pharmaceutical applications.

AB - All-trans-retinoic acid (RA) was chemically conjugated to biodegradable poly(ε-caprolactone) (PCL10; number-average Mw ≈ 1250) via an ester linkage. The conjugation was carried out using N,N-dicyclohexylcarbodiimide and 4-dimethyl aminopyridine as a coupling agent. The molar ratio of the drug to the polymer was 1.11 as determined by 1H-NMR analysis. DSC and WAXD results showed that the formation of crystalline structures of RA was effectively suppressed by conjugation with PCL. The RA-PCL conjugates were formulated into nanoparticles by a spontaneous phase-inversion technique. Morphological characteristics of the resultant nanoparticles and drug-loading efficiencies were compared with those of free RA-loaded nanoparticles. The drug-loading efficiency of RA-PCL conjugates was almost 100%, while that of free RA was only ∼12%. The majority of unconjugated RA was found to form undesirable free-drug crystals out of nanoparticles, as observed by TEM analysis. This study demonstrates that the conjugation approach of RA to PCL can be an effective means to Immobilize and encapsulate RA within nanoparticles for pharmaceutical applications.

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KW - Biological applications of polymers

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KW - Nanotechnology

KW - Polyesters

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Chemical immobilization of retinoic acid within poly(ε-caprolactone) nanoparticles based on drug-polymer bioconjugates

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