ArticleMolecular pharmaceutics2013
Peptide amphiphile containing arginine and fatty acyl chains as molecular transporters.
Article in Molecular pharmaceutics, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Palmitic Acid-Conjugated Radiopharmaceutical for Integrin αPharmaceutics · 2022Article
- Recent advances in peptide-based nanomaterials for targeting hypoxia.Nanoscale advances · 2021Review
- Cytoplasmic synthesis of endogenousProceedings of the National Academy of Sciences of the United States of America · 2021Article
- Cytotoxicity and Immunogenicity Evaluation of Synthetic Cell-penetrating Peptides for Methotrexate Delivery.Iranian journal of pharmaceutical research : IJPR · 2021Article
- Efficient Intracellular Delivery of Cell-Impermeable Cargo Molecules by Peptides Containing Tryptophan and Histidine.Molecules (Basel, Switzerland) · 2018Article
- Article
- Synthesis and in vitro evaluation of amphiphilic peptides and their nanostructured conjugates.Advanced pharmaceutical bulletin · 2015Article
- Cyclic peptide-selenium nanoparticles as drug transporters.Molecular pharmaceutics · 2014Article
- Enhanced cellular entry and efficacy of tat conjugates by rational design of the auxiliary segment.Molecular pharmaceutics · 2014Article
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7 authors.
Funding
Abstract
Peptide amphiphiles (PAs) are promising tools for the intracellular delivery of numerous drugs. PAs are known to be biodegradable systems. Here, four PA derivatives containing arginine and lysine conjugated with fatty acyl groups with different chain lengths, namely, PA1: R-K(C14)-R, PA2: R-K(C16)-R, PA3: K(C14)-R-K(C14), and PA4: K(C16)-R-K(C16), where C16 = palmitic acid and C14 = myristic acid, were synthesized through Fmoc chemistry. Flow cytometry studies showed that, among all synthesized PAs, only K(C16)-R-K(C16), PA4 was able to enhance the cellular uptake of a fluorescence-labeled anti-HIV drug 2',3'-dideoxy-3'-thiacythidine (F'-3TC, F' = fluorescein) and a biologically important phosphopeptide (F'-PEpYLGLD) in human leukemia cells (CCRF-CEM) after 2 h incubation. For example, the cellular uptake of F'-3TC and F'-PEpYLGLD was enhanced approximately 7.1- and 12.6-fold in the presence of the PA4 compared to those of the drugs alone. Confocal microscopy of F'-3TC and F'-PEpYLGLD loaded PA4 in live cells showed significantly higher intracellular localization than the drug alone in human ovarian cells (SK-OV-3) after 2 h incubation. The high-performance liquid chromatography (HPLC) results showed that loading of Dox by the peptide amphiphile was 56% after 24 h. The loaded Dox was released (34%) within 48 h intracellularly. The circular dichrosim (CD) results exhibited that the secondary structure of the peptide was changed upon interactions with Dox. Mechanistic studies revealed that endocytosis is the major pathway of the internalization. These studies suggest that PAs containing the appropriate sequence of amino acids, chain length, charge, and hydrophobicity can be used as cellular delivery tools for transporting drugs and biomolecules.
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