Synthesis, penetrability and intracellular targeting of fluorescein-tagged peptoids and peptide–peptoid hybrids
| Autor: | Mark Bradley, Mario Antonio Fara, Asier Unciti-Broceta, Franziska Diezmann, Chiung Ying Ou-Yang |
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| Rok vydání: | 2009 |
| Předmět: |
Cell Membrane Permeability
Peptidomimetic Clinical Biochemistry Pharmaceutical Science Biochemistry Flow cytometry law.invention HeLa Mice Peptoids chemistry.chemical_compound Solid-phase synthesis Confocal microscopy law Cell Line Tumor Drug Discovery medicine Animals Humans Amino Acid Sequence Fluorescein Molecular Biology Fluorescent Dyes Cell Nucleus medicine.diagnostic_test biology Chemistry Organic Chemistry Biological Transport Peptoid Flow Cytometry biology.organism_classification Cell culture Molecular Medicine Peptides HeLa Cells |
| Zdroj: | Bioorganic & Medicinal Chemistry. 17:959-966 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2008.02.068 |
| Popis: | The search for novel, generally applicable and highly efficient delivery tools is a major activity in the biotechnology arena. Using highly optimized microwave based solid-phase chemistry a series of fluorescein-labelled cationic peptoid conjugates were synthesized within 24h and cellular uptake into HeLa, L929 and K562 cells examined via flow cytometry. As expected, analysis revealed that longer oligomers achieved greater cellular penetration (7e (9 mer)>7d (7 mer)>7c (5 mer)>7b (3 mer)>7a (1 mer)) with the nonamer 7e proving to be a remarkable vehicle for all the cell lines, showing excellent penetrability into K562 and L929 cells and extraordinary cell delivery into HeLa cells. Confocal microscopy showed that the hybrid peptoid-nuclear localizing sequence (PKKKRKV from the simian virus 40 large T antigen) resulted in very high levels of nuclei delivery after 3h, opening up a range of applications such as nuclei staining of living cells with non-DNA-intercalating fluorescent probes. |
| Databáze: | OpenAIRE |
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