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Design and synthesis of pH-sensitive polyamino-ester magneto-dendrimers: Surface functional groups effect on viability of human prostate carcinoma cell lines DU145.

European journal of medicinal chemistry (2015-05-30)
Nahid Dayyani, Sepideh Khoee, Ali Ramazani
ABSTRACT

Novel pH-sensitive, biocompatible and biodegradable magneto-dendrimers with OH and/or NH2 functional groups based on poly amino-ester were synthesized for delivery of anti-cancer drugs. Magnetite nanoparticles (MNPs) were synthesized by the co-precipitation method and their surfaces were modified by 3-aminopropyl triethoxysilane. The first and second generations of the magneto-dendrimer with hydroxyl end groups were produced by sequential acrylation and Michael addition reactions using the required amounts of acryloyl chloride and diethanolamine, respectively. The dendrimer containing amino functional surface groups up to second generation was synthesized by the same method using the necessary amounts of acryloyl chloride and ethylenediamine. These dendrimers were fully characterized by the Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), dynamic light scattering (DLS) and zeta potential analysis, vibrating-sample magnetometer (VSM), scanning electron microscope (SEM), transmission electron microscopy (TEM) and selected area electron diffraction (SAED). In-vitro release profiles of the drug-loaded magnetic nanoparticles and their cytotoxicity assay were investigated at two pHs (7.4 and 5.8). The hydrolytic degradation behavior of magneto-dendrimers was evaluated in PBS buffer. Our research suggests that magneto-dendrimers having amine or hydroxyl functional groups could be considered as the suitable nanocarriers for therapy applications.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethylenediamine, BioXtra
Sigma-Aldrich
Ethylenediamine solution, technical, 75-80%
Sigma-Aldrich
(3-Aminopropyl)triethoxysilane, ≥98%
Sigma-Aldrich
Ethylenediamine, purified by redistillation, ≥99.5%
Sigma-Aldrich
(3-Aminopropyl)triethoxysilane, packaged for use in deposition systems, ≥98%
Sigma-Aldrich
Methanol-12C, 99.95 atom % 12C
Sigma-Aldrich
Ethylenediamine, ReagentPlus®, ≥99%
Sigma-Aldrich
Ethylenediamine, meets USP testing specifications
Sigma-Aldrich
Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer
Sigma-Aldrich
(3-Aminopropyl)triethoxysilane, 99%
Sigma-Aldrich
Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer
Supelco
Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 5 mm × 8 in.
Sigma-Aldrich
Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 3 mm × 8 in.
Sigma-Aldrich
(3-Aminopropyl)triethoxysilane, ≥98.0%
Sigma-Aldrich
Diethanolamine, reagent grade, ≥98.0%
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Triethylamine, for amino acid analysis, ≥99.5% (GC)
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Triethylamine, for protein sequence analysis, ampule, ≥99.5% (GC)
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Diethanolamine, BioUltra, ≥99.5% (GC)
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Triethylamine, BioUltra, ≥99.5% (GC)
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Triethylamine, puriss. p.a., ≥99.5% (GC)
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N,N-Diethylaniline, ≥99%
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Acetone, ≥99%, meets FCC analytical specifications
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Diethanolamine, ACS reagent, ≥98.5%
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Triethylamine, ≥99.5%
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Diethanolamine, puriss. p.a., ACS reagent, ≥99.0% (GC)
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Methanol, anhydrous, 99.8%
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Acetone, suitable for HPLC, ≥99.9%
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Triethylamine, ≥99%
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Ammonia-14N, 99.99 atom % 14N
Sigma-Aldrich
Acetone, natural, ≥97%