Synthesis and characterization of fluorescein isothiocyanate (FITC)-labeled PEO–PCL–PEO triblock copolymers for topical delivery
We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)- block-poly(ɛ-caprolactone)- block-poly(ethylene oxide) (PEO–PCL–PEO) triblock copolymers and their applications for tracking the penetration behavior of FITC-labeled copolymers in the hairless mouse skin. In...
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| Published in | Polymer (Guilford) Vol. 50; no. 11; pp. 2357 - 2364 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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Kidlington
Elsevier Ltd
22.05.2009
Elsevier |
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| Abstract | We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)-
block-poly(ɛ-caprolactone)-
block-poly(ethylene oxide) (PEO–PCL–PEO) triblock copolymers and their applications for tracking the penetration behavior of FITC-labeled copolymers in the hairless mouse skin. In the first step, PEO–PCL diblock copolymers with different ratios of PCL to PEO (i.e., [CL]/[EO]) were prepared by ring opening polymerization of ɛ-caprolactone (CL), where monomethoxy poly(ethylene glycol) (mPEG,
M
n
=
2000
g
mol
−1) was used as a macro-initiator. FITC was successively reacted with octadecylamine, isophorone diisocyanate (IPDI), and then used as a linker to obtain PEO–PCL–PEO triblock copolymers from the PEO–PCL diblock copolymers. In aqueous solution, both FITC-labeled triblock copolymers show two UV absorption peaks at 489 and 455
nm, attributed to the monomeric FITC and H-aggregated FITC moieties, respectively. Due to the strong H-aggregation of FITC in the copolymer of high [CL]/[EO], fluorescent emission intensities considerably decreased at high concentrations of the copolymer. FITC-labeled copolymers exhibited more sharper polarized optical and fluorescence microscopic images compared to the mixtures of FITC and unlabeled copolymer in both solid crystalline and multiple emulsion state. Furthermore, the Frantz diffusion cell test was carried out to demonstrate the penetration behavior of the FITC-labeled copolymers in the hairless mouse skin.
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| AbstractList | We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)-
block-poly(ɛ-caprolactone)-
block-poly(ethylene oxide) (PEO–PCL–PEO) triblock copolymers and their applications for tracking the penetration behavior of FITC-labeled copolymers in the hairless mouse skin. In the first step, PEO–PCL diblock copolymers with different ratios of PCL to PEO (i.e., [CL]/[EO]) were prepared by ring opening polymerization of ɛ-caprolactone (CL), where monomethoxy poly(ethylene glycol) (mPEG,
M
n
=
2000
g
mol
−1) was used as a macro-initiator. FITC was successively reacted with octadecylamine, isophorone diisocyanate (IPDI), and then used as a linker to obtain PEO–PCL–PEO triblock copolymers from the PEO–PCL diblock copolymers. In aqueous solution, both FITC-labeled triblock copolymers show two UV absorption peaks at 489 and 455
nm, attributed to the monomeric FITC and H-aggregated FITC moieties, respectively. Due to the strong H-aggregation of FITC in the copolymer of high [CL]/[EO], fluorescent emission intensities considerably decreased at high concentrations of the copolymer. FITC-labeled copolymers exhibited more sharper polarized optical and fluorescence microscopic images compared to the mixtures of FITC and unlabeled copolymer in both solid crystalline and multiple emulsion state. Furthermore, the Frantz diffusion cell test was carried out to demonstrate the penetration behavior of the FITC-labeled copolymers in the hairless mouse skin.
▪ We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)-block-poly(?-caprolactone)-block-poly(ethylene oxide) (PEO-PCL-PEO) triblock copolymers and their applications for tracking the penetration behavior of FITC-labeled copolymers in the hairless mouse skin. In the first step, PEO-PCL diblock copolymers with different ratios of PCL to PEO (i.e., [CL]/[EO]) were prepared by ring opening polymerization of ?-caprolactone (CL), where monomethoxy poly(ethylene glycol) (mPEG, M@dn=2000gmol@u-@u1) was used as a macro-initiator. FITC was successively reacted with octadecylamine, isophorone diisocyanate (IPDI), and then used as a linker to obtain PEO-PCL-PEO triblock copolymers from the PEO-PCL diblock copolymers. In aqueous solution, both FITC-labeled triblock copolymers show two UV absorption peaks at 489 and 455nm, attributed to the monomeric FITC and H-aggregated FITC moieties, respectively. Due to the strong H-aggregation of FITC in the copolymer of high [CL]/[EO], fluorescent emission intensities considerably decreased at high concentrations of the copolymer. FITC-labeled copolymers exhibited more sharper polarized optical and fluorescence microscopic images compared to the mixtures of FITC and unlabeled copolymer in both solid crystalline and multiple emulsion state. Furthermore, the Frantz diffusion cell test was carried out to demonstrate the penetration behavior of the FITC-labeled copolymers in the hairless mouse skin. |
| Author | Choi, Sung Wook Cheong, In Woo Cho, Heui Kyoung Lone, Saifullah Kim, Dae Duk Kim, Jung Hyun Choi, Joon Ho Cho, Jin Hun |
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| Keywords | Fluorescein isothiocyanate PEO–PCL–PEO Biodegradable Ring opening polymerization Fluorescence spectrum Fluorescent tracer Drug carrier PEO-PCL-PEO Caprolactone copolymer Labelled copolymer Spherulites Water oil water emulsion Molecular aggregation Amphiphilic polymer Transdermal system Control release polymer Rodentia Ethylene oxide copolymer Experimental study Absorption spectrum Monodispersed polymer Vertebrata Triblock copolymer Mammalia Mouse Animal Morphology Preparation Concentration effect Aqueous solution Topical administration |
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| Snippet | We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)-
block-poly(ɛ-caprolactone)-
block-poly(ethylene oxide)... We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)-block-poly(?-caprolactone)-block-poly(ethylene oxide) (PEO-PCL-PEO)... |
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| SubjectTerms | Applied sciences Biodegradable Biological and medical sciences Exact sciences and technology Fluorescein isothiocyanate General pharmacology Medical sciences Organic polymers PEO–PCL–PEO Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Physicochemistry of polymers Polymers with particular properties Preparation, kinetics, thermodynamics, mechanism and catalysts |
| Title | Synthesis and characterization of fluorescein isothiocyanate (FITC)-labeled PEO–PCL–PEO triblock copolymers for topical delivery |
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