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Drug nanocarrier agents based on starch-g-amino acids.

ABSTRACT: Introduction: In the recent decades, starch has been modified using different methods for the various forms of applications. Some new starch derivatives were prepared through a simple and convenient method in the grafting of amino acids: L-alanine, L-leucine and L-phenyl alanine to starch. Methods: First, the amine groups of amino acids were protected using phthalic anhydride then the acidic side of amino acids were activated with chlorination using thionyl chloride, and the resultant acid chlorides were reacted with starch in aqueous media at room temperature. Results: Performing the various spectroscopy experiments on the obtained compounds showed that the new derivative of starch has been formed. The structure of all synthesized materials was determined and confirmed using common spectroscopy methods and their thermal behavior was examined using DSC experiment. Conclusion: New amino acid derivatives of starch and their nanocarriers successfully prepared through a simple and convenient method. The size of nanocarriers evaluated using DLS and TEM experiments. The spherical shape of particles shows that nanocarriers have been formed and the size of these particles are approximately 92, 137 and 97 nm. Performing the wettability test determined that all the resulted materials are soluble in water. Nanocarriers of the obtained modified starches were prepared using dialysis method and naproxen was utilized as a model drug molecule. The drug release dynamics in buffered solution were studied and investigation of the drug release mechanism showed that in case of L-alanine- and L-phenylalanine-modified starches, drug release followed the Fickian diffusion with a slight deviation.

SUBMITTER: Namazi H

PROVIDER: S-EPMC6026521 | biostudies-other | 2018

REPOSITORIES: biostudies-other

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Drug nanocarrier agents based on starch-g-amino acids.

Namazi Hassan H Abdollahzadeh Elnaz E

BioImpacts : BI 20171128 2

Introduction: In the recent decades, starch has been modified using different methods for the various forms of applications. Some new starch derivatives were prepared through a simple and convenient method in the grafting of amino acids: L-alanine, L-leucine and L-phenyl alanine to starch. Methods: First, the amine groups of amino acids were protected using phthalic anhydride then the acidic side of amino acids were activated with chlorination using thionyl chloride, ...[more]

PMID: 29977831

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Project description:A series of cyclic peptides, [(DipR)(WR)4], [(DipR)2(WR)3], [(DipR)3(WR)2], [(DipR)4(WR)], and [DipR]5, and their linear counterparts containing arginine (R) as positively charged residues and tryptophan (W) or diphenylalanine (Dip) as hydrophobic residues, were synthesized and evaluated for their molecular transporter efficiency. The in vitro cytotoxicity of the synthesized peptides was determined in human epithelial ovary adenocarcinoma cells (SK-OV-3), human lymphoblast peripheral blood cells (CCRF-CEM), human embryonic epithelial kidney healthy cells (HEK-293), human epithelial mammary gland adenocarcinoma cells (MDA-MB-468), pig epithelial kidney normal cells (LLC-PK1), and human epithelial fibroblast uterine sarcoma cells (MES-SA). A concentration of 5-10 µM and 3 h incubation were selected in uptake studies. The cellular uptake of a fluorescent-labeled phosphopeptide, stavudine, lamivudine, emtricitabine, and siRNA was determined in the presence of peptides via flow cytometry. Among the peptides, [DipR]5 (10 µM) was found to be the most efficient transporter and significantly improved the uptake of F'-GpYEEI, i.e., by approximately 130-fold after 3 h incubation in CCRF-CEM cells. Confocal microscopy further confirmed the improved delivery of fluorescent-labeled [DipR]5 (F'-[K(DipR)5]) alone and F'-GpYEEI in the presence of [DipR]5 in MDA-MB-231 cells. The uptake of fluorescent-labeled siRNA (F'-siRNA) in the presence of [DipR]5 with N/P ratios of 10 and 20 was found to be 30- and 50-fold higher, respectively, compared with the cells exposed to F'-siRNA alone. The presence of endocytosis inhibitors, i.e., nystatin, chlorpromazine, chloroquine, and methyl β-cyclodextrin, did not completely inhibit the cellular uptake of F'-[K(DipR)5] alone or F'-GpYEEI in the presence of [DipR]5, suggesting that a combination of mechanisms contributes to uptake. Circular dichroism was utilized to determine the secondary structure, while transmission electron microscopy was used to evaluate the particle sizes and morphology of the peptides. The data suggest the remarkable membrane transporter property of [DipR]5 for improving the delivery of various small molecules and cell-impermeable negatively charged molecules (e.g., siRNA and phosphopeptide).

Dataset Information

Drug nanocarrier agents based on starch-g-amino acids.

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Drug nanocarrier agents based on starch-g-amino acids.

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