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Title: Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences

Journal Article · · ACS Central Science

Cell penetrating peptides (CPPs) are intriguing molecules that have received much attention, both in terms of mechanistic analysis and as transporters for intracellular therapeutic delivery. Most CPPs contain an abundance of cationic charged residues, typically arginine, where the amino acid compositions, rather than specific sequences, tend to determine their ability to enter cells. Hydrophobic residues are often added to cationic sequences to create efficient CPPs, but typically at the penalty of increased cytotoxicity. Here, we examined polypeptides containing glycosylated, cationic derivatives of methionine, where we found these hydrophilic polypeptides to be surprisingly effective as CPPs and to also possess low cytotoxicity. X-ray analysis of how these new polypeptides interact with lipid membranes revealed that the incorporation of sterically demanding hydrophilic cationic groups in polypeptides is an unprecedented new concept for design of potent CPPs.

Research Organization:
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
AC02-76SF00515; 1308081
OSTI ID:
1215430
Journal Information:
ACS Central Science, Vol. 1, Issue 2; ISSN 2374-7943
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 23 works
Citation information provided by
Web of Science

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Cited By (7)

Cellular uptake: lessons from supramolecular organic chemistry journal January 2015
Design of therapeutically improved analogue of the antimicrobial peptide, indolicidin, using a glycosylation strategy journal September 2019
Homoallylglycine residues are superior precursors to orthogonally modified thioether containing polypeptides journal January 2018
Methionine-based cationic polypeptide/polypeptide block copolymer with triple-stimuli responsiveness: DNA polyplexation and phototriggered release journal January 2018
Cell-Translocation Mechanisms of CPPs book June 2019
Cell-penetrating peptides with intracellular organelle targeting journal August 2016
The importance of the glycosylation of antimicrobial peptides: natural and synthetic approaches journal June 2017

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