Document Detail


An efficient biodelivery system for antisense polyamide nucleic acid (PNA).
MedLine Citation:
PMID:  18707540     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
With the aim of developing a general and straightforward procedure for the intracellular delivery of naked peptide nucleic acids (PNAs), we designed an intracellularly biodegradable triphenylphosphonium (TPP) cation based transporter system. In this system, TPP is linked, via a biolabile disulfide bridge, to an activated mercaptoethoxycarbonyl moiety, allowing its direct coupling to the N-terminal extremity of a free PNA through a carbamate bond. We found that such TPP-PNA-carbamate conjugates were highly stable in a cell culture medium containing fetal calf serum. In a glutathione-containing medium mimicking the cytosol, the conjugates were rapidly degraded into an unstable intermediate, which spontaneously decomposed, releasing the free PNA. Using a fluorescence-labeled PNA-TPP conjugate, we demonstrated that conjugates were taken up by cells. Efficient cellular uptake and release of the PNA into the cytosol was further confirmed by the anti-HIV activity measured for the TPP-conjugate of a 16-mer PNA targeting the TAR region of the HIV-1 genome. This conjugate exhibited an IC(50) value of 1 microM, while the free 16-mer PNA did not inhibit replication of HIV in the same cellular test.
Authors:
Mohamed Mehiri; Gregory Upert; Snehlata Tripathi; Audrey Di Giorgio; Roger Condom; Virendra N Pandey; Nadia Patino
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Oligonucleotides     Volume:  18     ISSN:  1557-8526     ISO Abbreviation:  Oligonucleotides     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-09-15     Completed Date:  2009-04-13     Revised Date:  2011-06-06    
Medline Journal Info:
Nlm Unique ID:  101188415     Medline TA:  Oligonucleotides     Country:  United States    
Other Details:
Languages:  eng     Pagination:  245-56     Citation Subset:  IM    
Affiliation:
Laboratoire de Chimie des Molécules Bioactives et des Arômes, Université de Nice-Sophia Antipolis-CNRS, Institut de Chimie de Nice, Nice, France.
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MeSH Terms
Descriptor/Qualifier:
Anti-HIV Agents / metabolism,  pharmacology
Antisense Elements (Genetics)*
Cell Line
Culture Media
Drug Delivery Systems*
HIV Long Terminal Repeat / drug effects
HIV-1 / drug effects,  genetics,  physiology
Humans
Nylons / chemistry,  metabolism*
Peptide Nucleic Acids / chemical synthesis,  metabolism*,  pharmacology
Virus Replication / drug effects
Grant Support
ID/Acronym/Agency:
AI42520/AI/NIAID NIH HHS
Chemical
Reg. No./Substance:
0/Anti-HIV Agents; 0/Antisense Elements (Genetics); 0/Culture Media; 0/Nylons; 0/Peptide Nucleic Acids

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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