Document Detail


Synthesis, penetrability and intracellular targeting of fluorescein-tagged peptoids and peptide-peptoid hybrids.
MedLine Citation:
PMID:  18343124     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Asier Unciti-Broceta; Franziska Diezmann; Chiung Ying Ou-Yang; Mario Antonio Fara; Mark Bradley
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-02-26
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  17     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2009-02-03     Completed Date:  2009-04-15     Revised Date:  2014-02-19    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  959-66     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amino Acid Sequence
Animals
Biological Transport
Cell Line, Tumor
Cell Membrane Permeability
Cell Nucleus / chemistry
Flow Cytometry
Fluorescein / chemistry*
Fluorescent Dyes / chemistry*
HeLa Cells
Humans
Mice
Peptides / chemical synthesis*,  chemistry,  metabolism*
Peptoids / chemical synthesis*,  chemistry,  metabolism*
Grant Support
ID/Acronym/Agency:
G0401194//Medical Research Council
Chemical
Reg. No./Substance:
0/Fluorescent Dyes; 0/Peptides; 0/Peptoids; 2321-07-5/Fluorescein

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