Synthesis, characterization and drug delivery behaviors of new PCP polymeric micelles

Der Zen Liu, Jui Hsiang Hsieh, Xian Chan Fan, Jean Dean Yang, Tze Wen Chung

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A new PCP tri-block copolymer consisting of poly (ε-caprolactone)-b-chitooligosaccharide-b-poly(ethylene glycol) (PCL-b-COS-b-PEG, PCP) was synthesized and characterized. The potential for delivering doxorubicin (DOX), a model drug, with or without genipin crosslinking was evaluated. The PCP copolymers were analyzed by Fourier-transform infrared spectrometry (FT-IR) to confirm the amine and ester groups of the COS and the PCL of the copolymer, respectively. 1H nuclear magnetic resonance (1H NMR) was performed to determine the structure of the PCP copolymer for demonstrating both PCL and PEG blocks grafted onto the COS block. Moreover, gel permeation chromatography (GPC) was applied to determine the number average molecular weight of the tri-block copolymer (Mn), which was 11,340 Da/mole. The PCP form polymeric micelles at the critical micelle concentration (CMC) of 0.0107 wt% (or 1.0 μM) with the mean diameter 90 nm, as determined by a dynamic light-scattering (DLS) analyzer. Since PCP micelles contain COS, the zeta potentials of the micelles are changed from a neutral (e.g., -3.2 ± 1.3 mV at pH 7.4) to a cationic state (13.9 ± 4.4 mV at pH 3.0) when pH values of the suspension medium are varied. This change is a unique property of the micelles. In addition, drug delivery behavior of the PCP micelles is influenced by genipin crosslinking COS. The DOX release period of crosslinked micelles is significantly longer than that of the non-crosslinked ones (e.g., 8 days vs. 4 days, respectively) while the burst release of DOX of crosslinked ones is significantly reduced compared with that of non-crosslinked ones. In conclusion, a new tri-block COS-containing PCP copolymer/polymeric micelle has been synthesized and characterized. Moreover, the unique properties of COS-containing PCP micelles are demonstrated by varying zeta potentials via changing pH of medium and by influencing DOX delivering behaviors after genipin crosslinking.

Original languageEnglish
Pages (from-to)544-554
Number of pages11
JournalCarbohydrate Polymers
Volume68
Issue number3
DOIs
Publication statusPublished - Apr 5 2007

Fingerprint

Micelles
micelles
Drug delivery
Polyethylene glycols
composite polymers
drugs
synthesis
doxorubicin
Pharmaceutical Preparations
Doxorubicin
crosslinking
Copolymers
Crosslinking
Zeta potential
Block copolymers
chitooligosaccharides
Ethylene Glycol
light scattering
Fourier Analysis
polyethylene glycol

Keywords

  • Chitooligosaccharide (COS)
  • Drug delivery
  • Genipin
  • Poly(ε-caprolactone)
  • Polymeric micelles

ASJC Scopus subject areas

  • Food Science
  • Biochemistry

Cite this

Synthesis, characterization and drug delivery behaviors of new PCP polymeric micelles. / Liu, Der Zen; Hsieh, Jui Hsiang; Fan, Xian Chan; Yang, Jean Dean; Chung, Tze Wen.

In: Carbohydrate Polymers, Vol. 68, No. 3, 05.04.2007, p. 544-554.

Research output: Contribution to journalArticle

Liu, Der Zen ; Hsieh, Jui Hsiang ; Fan, Xian Chan ; Yang, Jean Dean ; Chung, Tze Wen. / Synthesis, characterization and drug delivery behaviors of new PCP polymeric micelles. In: Carbohydrate Polymers. 2007 ; Vol. 68, No. 3. pp. 544-554.
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abstract = "A new PCP tri-block copolymer consisting of poly (ε-caprolactone)-b-chitooligosaccharide-b-poly(ethylene glycol) (PCL-b-COS-b-PEG, PCP) was synthesized and characterized. The potential for delivering doxorubicin (DOX), a model drug, with or without genipin crosslinking was evaluated. The PCP copolymers were analyzed by Fourier-transform infrared spectrometry (FT-IR) to confirm the amine and ester groups of the COS and the PCL of the copolymer, respectively. 1H nuclear magnetic resonance (1H NMR) was performed to determine the structure of the PCP copolymer for demonstrating both PCL and PEG blocks grafted onto the COS block. Moreover, gel permeation chromatography (GPC) was applied to determine the number average molecular weight of the tri-block copolymer (Mn), which was 11,340 Da/mole. The PCP form polymeric micelles at the critical micelle concentration (CMC) of 0.0107 wt{\%} (or 1.0 μM) with the mean diameter 90 nm, as determined by a dynamic light-scattering (DLS) analyzer. Since PCP micelles contain COS, the zeta potentials of the micelles are changed from a neutral (e.g., -3.2 ± 1.3 mV at pH 7.4) to a cationic state (13.9 ± 4.4 mV at pH 3.0) when pH values of the suspension medium are varied. This change is a unique property of the micelles. In addition, drug delivery behavior of the PCP micelles is influenced by genipin crosslinking COS. The DOX release period of crosslinked micelles is significantly longer than that of the non-crosslinked ones (e.g., 8 days vs. 4 days, respectively) while the burst release of DOX of crosslinked ones is significantly reduced compared with that of non-crosslinked ones. In conclusion, a new tri-block COS-containing PCP copolymer/polymeric micelle has been synthesized and characterized. Moreover, the unique properties of COS-containing PCP micelles are demonstrated by varying zeta potentials via changing pH of medium and by influencing DOX delivering behaviors after genipin crosslinking.",
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N2 - A new PCP tri-block copolymer consisting of poly (ε-caprolactone)-b-chitooligosaccharide-b-poly(ethylene glycol) (PCL-b-COS-b-PEG, PCP) was synthesized and characterized. The potential for delivering doxorubicin (DOX), a model drug, with or without genipin crosslinking was evaluated. The PCP copolymers were analyzed by Fourier-transform infrared spectrometry (FT-IR) to confirm the amine and ester groups of the COS and the PCL of the copolymer, respectively. 1H nuclear magnetic resonance (1H NMR) was performed to determine the structure of the PCP copolymer for demonstrating both PCL and PEG blocks grafted onto the COS block. Moreover, gel permeation chromatography (GPC) was applied to determine the number average molecular weight of the tri-block copolymer (Mn), which was 11,340 Da/mole. The PCP form polymeric micelles at the critical micelle concentration (CMC) of 0.0107 wt% (or 1.0 μM) with the mean diameter 90 nm, as determined by a dynamic light-scattering (DLS) analyzer. Since PCP micelles contain COS, the zeta potentials of the micelles are changed from a neutral (e.g., -3.2 ± 1.3 mV at pH 7.4) to a cationic state (13.9 ± 4.4 mV at pH 3.0) when pH values of the suspension medium are varied. This change is a unique property of the micelles. In addition, drug delivery behavior of the PCP micelles is influenced by genipin crosslinking COS. The DOX release period of crosslinked micelles is significantly longer than that of the non-crosslinked ones (e.g., 8 days vs. 4 days, respectively) while the burst release of DOX of crosslinked ones is significantly reduced compared with that of non-crosslinked ones. In conclusion, a new tri-block COS-containing PCP copolymer/polymeric micelle has been synthesized and characterized. Moreover, the unique properties of COS-containing PCP micelles are demonstrated by varying zeta potentials via changing pH of medium and by influencing DOX delivering behaviors after genipin crosslinking.

AB - A new PCP tri-block copolymer consisting of poly (ε-caprolactone)-b-chitooligosaccharide-b-poly(ethylene glycol) (PCL-b-COS-b-PEG, PCP) was synthesized and characterized. The potential for delivering doxorubicin (DOX), a model drug, with or without genipin crosslinking was evaluated. The PCP copolymers were analyzed by Fourier-transform infrared spectrometry (FT-IR) to confirm the amine and ester groups of the COS and the PCL of the copolymer, respectively. 1H nuclear magnetic resonance (1H NMR) was performed to determine the structure of the PCP copolymer for demonstrating both PCL and PEG blocks grafted onto the COS block. Moreover, gel permeation chromatography (GPC) was applied to determine the number average molecular weight of the tri-block copolymer (Mn), which was 11,340 Da/mole. The PCP form polymeric micelles at the critical micelle concentration (CMC) of 0.0107 wt% (or 1.0 μM) with the mean diameter 90 nm, as determined by a dynamic light-scattering (DLS) analyzer. Since PCP micelles contain COS, the zeta potentials of the micelles are changed from a neutral (e.g., -3.2 ± 1.3 mV at pH 7.4) to a cationic state (13.9 ± 4.4 mV at pH 3.0) when pH values of the suspension medium are varied. This change is a unique property of the micelles. In addition, drug delivery behavior of the PCP micelles is influenced by genipin crosslinking COS. The DOX release period of crosslinked micelles is significantly longer than that of the non-crosslinked ones (e.g., 8 days vs. 4 days, respectively) while the burst release of DOX of crosslinked ones is significantly reduced compared with that of non-crosslinked ones. In conclusion, a new tri-block COS-containing PCP copolymer/polymeric micelle has been synthesized and characterized. Moreover, the unique properties of COS-containing PCP micelles are demonstrated by varying zeta potentials via changing pH of medium and by influencing DOX delivering behaviors after genipin crosslinking.

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