Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences

Kramer, Jessica R.; Schmidt, Nathan W.; Mayle, Kristine M.; Kamei, Daniel T.; Wong, Gerard C.L.; Deming, Timothy J.

doi:10.1021/acscentsci.5b00054

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

Abstract

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.

Authors:

Kramer, Jessica R. ^[1]; Schmidt, Nathan W. ^[1]; Mayle, Kristine M. ^[1]; Kamei, Daniel T. ^[1]; Wong, Gerard C.L. ^[1]; Deming, Timothy J. ^[1]

Univ. of California, Los Angeles, CA (United States)

Publication Date:: Wed Apr 15 00:00:00 EDT 2015

Research Org.:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1215430

Grant/Contract Number:: AC02-76SF00515; 1308081

Resource Type:: Accepted Manuscript

Journal Name:: ACS Central Science

Additional Journal Information:: Journal Volume: 1; Journal Issue: 2; Journal ID: ISSN 2374-7943

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES

Citation Formats


                    Kramer, Jessica R., Schmidt, Nathan W., Mayle, Kristine M., Kamei, Daniel T., Wong, Gerard C.L., and Deming, Timothy J. Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences.  United States: N. p., 2015. 
Web.  doi:10.1021/acscentsci.5b00054.

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                    Kramer, Jessica R., Schmidt, Nathan W., Mayle, Kristine M., Kamei, Daniel T., Wong, Gerard C.L., & Deming, Timothy J. Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences.  United States.  https://doi.org/10.1021/acscentsci.5b00054

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                    Kramer, Jessica R., Schmidt, Nathan W., Mayle, Kristine M., Kamei, Daniel T., Wong, Gerard C.L., and Deming, Timothy J. Wed .  
"Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences".  United States.  https://doi.org/10.1021/acscentsci.5b00054.  https://www.osti.gov/servlets/purl/1215430.

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@article{osti_1215430,

  title        = {Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences},

  author       = {Kramer, Jessica R. and Schmidt, Nathan W. and Mayle, Kristine M. and Kamei, Daniel T. and Wong, Gerard C.L. and Deming, Timothy J.},

  abstractNote = {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.},

  doi          = {10.1021/acscentsci.5b00054},

  journal      = {ACS Central Science},

  number       = 2,

  volume       = 1,

  place        = {United States},

  year         = {Wed Apr 15 00:00:00 EDT 2015},

  month        = {Wed Apr 15 00:00:00 EDT 2015}

}

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Futaki, S.
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journal, November 2009

Schmidt, Nathan; Mishra, Abhijit; Lai, Ghee Hwee
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Hemp, Sean T.; Allen, Michael H.; Green, Matthew D.
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Criterion for Amino Acid Composition of Defensins and Antimicrobial Peptides Based on Geometry of Membrane Destabilization
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Journal of the American Chemical Society, Vol. 133, Issue 17
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Ornelas-Megiatto, Cátia; Wich, Peter R.; Fréchet, Jean M. J.
Journal of the American Chemical Society, Vol. 134, Issue 4
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journal, January 2013

Tang, Haoyu; Yin, Lichen; Kim, Kyung Hoon
Chemical Science, Vol. 4, Issue 10
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Translocation of HIV TAT peptide and analogues induced by multiplexed membrane and cytoskeletal interactions
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Mishra, A.; Lai, G. H.; Schmidt, N. W.
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Cellular uptake: lessons from supramolecular organic chemistry
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Cerrato, Carmine Pasquale; Künnapuu, Kadri; Langel, Ülo
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Title: Reinventing cell penetrating peptides using glycosylated methionine sulfonium ion sequences

Abstract

Citation Formats

The design of guanidinium-rich transporters and their internalization mechanisms journal, March 2008

Membrane-permeable arginine-rich peptides and the translocation mechanisms journal, February 2005

Tat peptide-mediated cellular delivery: back to basics journal, February 2005

Polyarginine enters cells more efficiently than other polycationic homopolymers: Cellular uptake of polyarginine journal, November 2000

Translocation of HIV TAT peptide and analogues induced by multiplexed membrane and cytoskeletal interactions journal, October 2011

Molecular Basis for Nanoscopic Membrane Curvature Generation from Quantum Mechanical Models and Synthetic Transporter Sequences journal, November 2012

HIV TAT Forms Pores in Membranes by Inducing Saddle-Splay Curvature: Potential Role of Bidentate Hydrogen Bonding journal, April 2008

Arginine-rich cell-penetrating peptides journal, November 2009

Criterion for Amino Acid Composition of Defensins and Antimicrobial Peptides Based on Geometry of Membrane Destabilization journal, May 2011

Helical poly(arginine) mimics with superior cell-penetrating and molecular transporting properties journal, January 2013

Polyphosphonium Polymers for siRNA Delivery: An Efficient and Nontoxic Alternative to Polyammonium Carriers journal, January 2012

Phosphonium-Containing Polyelectrolytes for Nonviral Gene Delivery journal, December 2011

Synthesis and Properties of Sulfonium Polyelectrolytes for Biological Applications journal, July 2013

Ternary Nylon-3 Copolymers as Host-Defense Peptide Mimics: Beyond Hydrophobic and Cationic Subunits journal, October 2014

Preparation of Multifunctional and Multireactive Polypeptides via Methionine Alkylation journal, May 2012

Reversible chemoselective tagging and functionalization of methionine containing peptides journal, January 2013

General Method for Purification of α-Amino acid- N -carboxyanhydrides Using Flash Chromatography journal, December 2010

How proteins produce cellular membrane curvature journal, November 2005

Generation and sensing of membrane curvature: Where materials science and biophysics meet journal, August 2013

Membrane bending by protein–protein crowding journal, August 2012

Hydrophobic moments and protein structure journal, January 1982

Cobalt and Iron Initiators for the Controlled Polymerization of α-Amino Acid- N -Carboxyanhydrides journal, June 1999

Polypeptide End-Capping Using Functionalized Isocyanates: Preparation of Pentablock Copolymers journal, April 2002

Fine Tuning of Vesicle Assembly and Properties Using Dual Hydrophilic Triblock Copolypeptides journal, April 2012

Fine Tuning of Vesicle Assembly and Properties Using Dual Hydrophilic Triblock Copolypeptides journal, April 2012

Membrane-permeable arginine-rich peptides and the translocation mechanisms journal, February 2005

Arginine-rich cell-penetrating peptides journal, November 2009

Antimicrobial peptides in insects; structure and function journal, June 1999

General Method for Purification of α-Amino acid- N -carboxyanhydrides Using Flash Chromatography journal, December 2010

Phosphonium-Containing Polyelectrolytes for Nonviral Gene Delivery journal, December 2011

Criterion for Amino Acid Composition of Defensins and Antimicrobial Peptides Based on Geometry of Membrane Destabilization journal, May 2011

Polyphosphonium Polymers for siRNA Delivery: An Efficient and Nontoxic Alternative to Polyammonium Carriers journal, January 2012

Molecular Basis for Nanoscopic Membrane Curvature Generation from Quantum Mechanical Models and Synthetic Transporter Sequences journal, November 2012

Bending membranes journal, September 2012

How proteins produce cellular membrane curvature journal, November 2005

Helical poly(arginine) mimics with superior cell-penetrating and molecular transporting properties journal, January 2013

Translocation of HIV TAT peptide and analogues induced by multiplexed membrane and cytoskeletal interactions journal, October 2011

Inverse lyotropic phases of lipids and membrane curvature journal, June 2006

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

The design of guanidinium-rich transporters and their internalization mechanisms
journal, March 2008

Membrane-permeable arginine-rich peptides and the translocation mechanisms
journal, February 2005

Tat peptide-mediated cellular delivery: back to basics
journal, February 2005

Polyarginine enters cells more efficiently than other polycationic homopolymers: Cellular uptake of polyarginine
journal, November 2000

Translocation of HIV TAT peptide and analogues induced by multiplexed membrane and cytoskeletal interactions
journal, October 2011

Molecular Basis for Nanoscopic Membrane Curvature Generation from Quantum Mechanical Models and Synthetic Transporter Sequences
journal, November 2012

HIV TAT Forms Pores in Membranes by Inducing Saddle-Splay Curvature: Potential Role of Bidentate Hydrogen Bonding
journal, April 2008

Arginine-rich cell-penetrating peptides
journal, November 2009

Criterion for Amino Acid Composition of Defensins and Antimicrobial Peptides Based on Geometry of Membrane Destabilization
journal, May 2011

Helical poly(arginine) mimics with superior cell-penetrating and molecular transporting properties
journal, January 2013

Polyphosphonium Polymers for siRNA Delivery: An Efficient and Nontoxic Alternative to Polyammonium Carriers
journal, January 2012

Phosphonium-Containing Polyelectrolytes for Nonviral Gene Delivery
journal, December 2011

Synthesis and Properties of Sulfonium Polyelectrolytes for Biological Applications
journal, July 2013

Ternary Nylon-3 Copolymers as Host-Defense Peptide Mimics: Beyond Hydrophobic and Cationic Subunits
journal, October 2014

Preparation of Multifunctional and Multireactive Polypeptides via Methionine Alkylation
journal, May 2012

Reversible chemoselective tagging and functionalization of methionine containing peptides
journal, January 2013

General Method for Purification of α-Amino acid- N -carboxyanhydrides Using Flash Chromatography
journal, December 2010

How proteins produce cellular membrane curvature
journal, November 2005

Generation and sensing of membrane curvature: Where materials science and biophysics meet
journal, August 2013

Membrane bending by protein–protein crowding
journal, August 2012

Hydrophobic moments and protein structure
journal, January 1982

Cobalt and Iron Initiators for the Controlled Polymerization of α-Amino Acid- N -Carboxyanhydrides
journal, June 1999

Polypeptide End-Capping Using Functionalized Isocyanates: Preparation of Pentablock Copolymers
journal, April 2002

Fine Tuning of Vesicle Assembly and Properties Using Dual Hydrophilic Triblock Copolypeptides
journal, April 2012

Fine Tuning of Vesicle Assembly and Properties Using Dual Hydrophilic Triblock Copolypeptides
journal, April 2012

Membrane-permeable arginine-rich peptides and the translocation mechanisms
journal, February 2005

Arginine-rich cell-penetrating peptides
journal, November 2009

Antimicrobial peptides in insects; structure and function
journal, June 1999

General Method for Purification of α-Amino acid- N -carboxyanhydrides Using Flash Chromatography
journal, December 2010

Phosphonium-Containing Polyelectrolytes for Nonviral Gene Delivery
journal, December 2011

Criterion for Amino Acid Composition of Defensins and Antimicrobial Peptides Based on Geometry of Membrane Destabilization
journal, May 2011

Polyphosphonium Polymers for siRNA Delivery: An Efficient and Nontoxic Alternative to Polyammonium Carriers
journal, January 2012

Molecular Basis for Nanoscopic Membrane Curvature Generation from Quantum Mechanical Models and Synthetic Transporter Sequences
journal, November 2012

Bending membranes
journal, September 2012

How proteins produce cellular membrane curvature
journal, November 2005

Helical poly(arginine) mimics with superior cell-penetrating and molecular transporting properties
journal, January 2013

Translocation of HIV TAT peptide and analogues induced by multiplexed membrane and cytoskeletal interactions
journal, October 2011

Inverse lyotropic phases of lipids and membrane curvature
journal, June 2006

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