Synthesis and characterization of functionalized poly(γ-benzyl-l-glutamate) derivates and corresponding nanoparticles preparation and characterization

Segura‐Sánchez, Freimar; Montembault, Véronique; Fontaine, Laurent; Martínez-Barbosa, María Elisa; Bouchemal, Kawthar; Ponchel, Gilles

doi:10.1016/j.ijpharm.2009.12.016

Cited by 23 publications

(23 citation statements)

References 43 publications

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“…The ROP of amino acid N-carboxy-anhydrides (NCA) is still the most commonly used technique to synthesize polypeptides, because of its simplicity and ease of product purification, 22 although some limitations of this anionic polymerization have been reported, such as the low reaction efficiency and broad molecular weight distribution of the resulting product due to incidental side reactions. 23 To improve the quality of this traditional reaction, several considerations have been taken into account in this experiment, in addition to the special care needed for purifying the solvents and reagents used.…”

Section: Resultsmentioning

confidence: 99%

Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers

Gu¹,

Xu²,

Sui³

et al. 2012

IJN

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Abstract:In this work, racemic hybrid polypeptides poly(ethylene glycol) (PEG)-bpoly(racemic-leucine) (PRL) copolymers with different leucine residues have been synthesized and characterized. Using docetaxel as a model molecule, the high drug-loaded spherical micelles based on PEG-PRL were prepared successfully using dialysis, with a tunable particle size from 170 nm to 250 nm obtained by changing the length of the hydrophobic blocks. Facilitated drugloading behavior (higher drug-loading ability and easier drug-loading process) of PEG-PRL compared with their corresponding levo forms (PEG-b-poly[levo leucine]) was observed and clarified for the first time. With this facilitation, the highest drug-loading content and efficiency of PEG-PRL micelles can achieve 11.2% ± 0.4% and 67.2% ± 2.4%, respectively. All drugloaded PEG-PRL micelles exhibit a similar release behavior with a sustained release up to 72 hours. The PEG-PRL was shown to be nontoxic against MCF-7 and human umbilical vein endothelial cells up to a concentration of 100 μg/mL, displaying a good biocompatibility. Also, the docetaxel-loaded PEG-PRL micelles were more toxic than the free drug against MCF-7 human breast cancer cells -both dose and time dependent. Therefore, these high docetaxel-loaded micelles based on racemic hybrid polypeptides appear to be a novel promising nanomedicine for anticancer therapy.

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Section: Resultsmentioning

confidence: 99%

Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers

Gu¹,

Xu²,

Sui³

et al. 2012

IJN

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“…2,29 To sum up, N millimoles of NCA were weighed under argon atmosphere in a degassed, three-necked, round-bottomed flask equipped with a ); intrinsic viscosity (η) was measured at 25°C. Furthermore, both copolymers (PBLGBnz and PBLG-PEG) were dissolved in deuteriochloroform (CDCl 3 ) in nuclear magnetic resonance (NMR) tubes, and 1 H-NMR spectras were recorded with a Bruker Advance (Bruker, Karlsruhe, Germany) spectrometer operated at 400 MHz.…”

Section: Synthesis Of Pblg Derivativesmentioning

confidence: 99%

“…Such a stability of FITC fluorescence in PBLG nanoparticles has been reported by Segura-Sánchez et al, who have shown that a water suspension of fluorescent nanoparticles has a stable fluorescence after 200-day storage, although free FITC water solutions are not very stable. 29 This suggests that FITC labeling of PBLG multifunctional nanoparticles is of interest for visualization and tracking purposes.…”

mentioning

confidence: 99%

Pegylation of poly(γ-benzyl-L-glutamate) nanoparticles is efficient for avoiding mononuclear phagocyte system capture in rats

Özcan¹,

Segura‐Sánchez²,

Bouchemal³

et al. 2010

IJN

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Poly(γ-benzyl-L-glutamate) (PBLG) derivatives are synthetic polypeptides for preparing nanoparticles with well controlled surface properties. The aim of this paper was to investigate the biodistribution of pegylated PBLG in rats. For this purpose, nanoparticles were prepared by a nanoprecipitation method using mixtures of different PBLG derivates, including a pegylated derivate to avoid mononuclear phagocyte system uptake. The morphology, size distribution, and surface charge of the nanoparticles were investigated as a function of the amount of polymer employed for the preparation. Moderately polydispersed nanoparticles (polydispersity index less than 0.2) were obtained. Their size increased with polymer concentration. The zeta potential values were negative whatever the formulations. The availability of polyethylene glycol chains on the nanoparticles' surface was confirmed by measuring the decrease in bovine serum albumin adsorption. For in vivo distribution studies, pegylated and nonpegylated nanoparticles were prepared with polymer mixtures containing PBLG-fluorescein isothiocyanate and imaged by fluorescence microscopy to measure their accumulation in liver and spleen tissues of rats after intravenous administration. Injection of stealth formulations resulted in negligible fluorescence in liver and spleen compared with nonpegylated formulations, which suggests that these nanoparticles are promising candidates as a stealth-type long-circulating drug carrier system and could be useful for active targeting of drugs while reducing systemic side effects.

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“…Carboxylic acids from PGlu were in the protonated state as evidenced by the band at 1710 cm −1 . PBLG-b-PGlu copolymer presented an α-helix structure, as shown by the amide I amide II and amide III bands at~1655 cm −1 ,~1550 cm −1 and~1260 cm −1 , respectively and the ester C=O band at 1735 cm −1 (see SM) (19)(20)(21).…”

Section: Synthesis and Characterization Of Pblg-b-pglu Copolymermentioning

confidence: 99%

Osteotropic Polypeptide Nanoparticles with Dual hydroxyapatite Binding Properties and Controlled Cisplatin Delivery

et al. 2014

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Synthesis and characterization of functionalized poly(γ-benzyl-l-glutamate) derivates and corresponding nanoparticles preparation and characterization

Cited by 23 publications

References 43 publications

Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers

Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers

Pegylation of poly(γ-benzyl-L-glutamate) nanoparticles is efficient for avoiding mononuclear phagocyte system capture in rats

Osteotropic Polypeptide Nanoparticles with Dual hydroxyapatite Binding Properties and Controlled Cisplatin Delivery

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Synthesis and characterization of functionalized poly(γ-benzyl-l-glutamate) derivates and corresponding nanoparticles preparation and characterization

Cited by 23 publications

References 43 publications

Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers

Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers

Pegylation of poly(&gamma;-benzyl-L-glutamate) nanoparticles is efficient for avoiding mononuclear phagocyte system capture in rats

Osteotropic Polypeptide Nanoparticles with Dual hydroxyapatite Binding Properties and Controlled Cisplatin Delivery

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Pegylation of poly(γ-benzyl-L-glutamate) nanoparticles is efficient for avoiding mononuclear phagocyte system capture in rats