Synthesis and characterization of star poly(ε-caprolactone)-b- poly(ethylene glycol) and poly(L-lactide)-b-poly(ethylene glycol) copolymers

Evaluation as drug delivery carriers

Fei Wang, Tatiana K Bronich, Alexander V. Kabanov, R. David Rauh, Jacques Roovers

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

Two types of 32 arm star polymers incorporating amphiphilic block copolymer arms have been synthesized and characterized. The first type, stPCL-PEG 32, is composed of a polyamidoamine (PAMAM) dendrimer as the core with radiating arms having poly(ε-caprolactone) (PCL) as an inner lipophilic block in the arm and poly(ethylene glycol) (PEG) as an outer hydrophilic block. The second type, StPLA-PEG32, is similar but with poly(L-lactide) (PLA) as the inner lipophilic block. Characterization with SEC, 1H NMR, FTIR, and DSC confirmed the structure of the polymers. Micelle formation by both star copolymers was studied by fluorescence spectroscopy. The stPCL-PEG32 polymer exhibited unimolecular micelle behavior. It was capable of solubilizing hydrophobic molecules, such as pyrene, in aqueous solution, while not displaying a critical micelle concentration. In contrast, the association behavior of stPLA-PEG32 in aqueous solution was characterized by an apparent critical micelle concentration of ca. 0.01 mg/mL. The hydrophobic anticancer drug etoposide can be encapsulated in the micelles formed from both polymers. Overall, the stPCL-PEG32 polymer exhibited a higher etoposide loading capacity (up to 7.8 w/w % versus 4.3 w/w % for StPLA-PEG32) as well as facile release kinetics and is more suitable as a potential drug delivery carrier.

Original languageEnglish (US)
Pages (from-to)1423-1429
Number of pages7
JournalBioconjugate Chemistry
Volume19
Issue number7
DOIs
StatePublished - Jul 1 2008

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Drug Carriers
Ethylene Glycol
Micelles
Drug delivery
Polyethylene glycols
Stars
Polymers
Copolymers
Critical micelle concentration
Etoposide
Dendrimers
Fluorescence Spectrometry
Pyrene
Fluorescence spectroscopy
Fourier Transform Infrared Spectroscopy
Block copolymers
Nuclear magnetic resonance
polycaprolactone
poly(lactide)
Association reactions

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Synthesis and characterization of star poly(ε-caprolactone)-b- poly(ethylene glycol) and poly(L-lactide)-b-poly(ethylene glycol) copolymers : Evaluation as drug delivery carriers. / Wang, Fei; Bronich, Tatiana K; Kabanov, Alexander V.; Rauh, R. David; Roovers, Jacques.

In: Bioconjugate Chemistry, Vol. 19, No. 7, 01.07.2008, p. 1423-1429.

Research output: Contribution to journalArticle

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abstract = "Two types of 32 arm star polymers incorporating amphiphilic block copolymer arms have been synthesized and characterized. The first type, stPCL-PEG 32, is composed of a polyamidoamine (PAMAM) dendrimer as the core with radiating arms having poly(ε-caprolactone) (PCL) as an inner lipophilic block in the arm and poly(ethylene glycol) (PEG) as an outer hydrophilic block. The second type, StPLA-PEG32, is similar but with poly(L-lactide) (PLA) as the inner lipophilic block. Characterization with SEC, 1H NMR, FTIR, and DSC confirmed the structure of the polymers. Micelle formation by both star copolymers was studied by fluorescence spectroscopy. The stPCL-PEG32 polymer exhibited unimolecular micelle behavior. It was capable of solubilizing hydrophobic molecules, such as pyrene, in aqueous solution, while not displaying a critical micelle concentration. In contrast, the association behavior of stPLA-PEG32 in aqueous solution was characterized by an apparent critical micelle concentration of ca. 0.01 mg/mL. The hydrophobic anticancer drug etoposide can be encapsulated in the micelles formed from both polymers. Overall, the stPCL-PEG32 polymer exhibited a higher etoposide loading capacity (up to 7.8 w/w {\%} versus 4.3 w/w {\%} for StPLA-PEG32) as well as facile release kinetics and is more suitable as a potential drug delivery carrier.",
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