2014
DOI: 10.1002/chem.201405381
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Design of Aromatic‐Containing Cell‐Penetrating Peptide Mimics with Structurally Modified π Electronics

Abstract: Cell penetrating peptides (CPPs) and their synthetic mimics (CPPMs) represent a class of molecules that facilitate the intracellular delivery of various cargo. Previous studies indicated that the presence of aromatic functionalities improved CPPM activity. Given that aromatic functionalities play prominent roles in membrane biology and participate in various π-interactions, we explored whether these interactions could be optimized for improved CPPM activity. CPPMs were synthesized by ring-opening metathesis po… Show more

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Cited by 34 publications
(42 citation statements)
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References 61 publications
(46 reference statements)
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“…Using R8 as inspiration and a benchmark, a 28,3136 set of four homopolymers and one block copolymer (Figure 1) were chosen to investigate the impact of polymer structure and backbone on internalization efficiency in HeLa cells.…”
Section: Introductionmentioning
confidence: 99%
“…Using R8 as inspiration and a benchmark, a 28,3136 set of four homopolymers and one block copolymer (Figure 1) were chosen to investigate the impact of polymer structure and backbone on internalization efficiency in HeLa cells.…”
Section: Introductionmentioning
confidence: 99%
“…To this end, our research group has devoted an extensive amount of research into understanding how the structures of ring-opening metathesis (ROMP) based protein mimics influence their membrane interactions 29,40,4448 , cellular uptake efficiencies 29,49 , and siRNA delivery. 30,32 We have demonstrated the utility of the platform for the successful internalization of siRNA and for the knockdown of active biological genes in T cells.…”
Section: Introductionmentioning
confidence: 99%
“…19,49,50 Initial studies aimed to understand the effects of PTDM length 51 , hydrophobicity 52 , aromaticity 53 , aromatic π-electronics 54 , and sequence segregation of cationic/hydrophobic components 55 on membrane interactions and cellular uptake. 43 In early 2013, we extended this platform to include siRNA delivery.…”
Section: Introductionmentioning
confidence: 99%