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PMID: 18393495 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, U.S. Gov't, Non-P.H.S.

A polymeric domain that promotes cellular internalization.

Journal of the American Chemical Society ·Vol. 130 ·No. 17 ·2008-04-30 ·Pages 5626-7

Kolonko EM, Kiessling LL

Abstract

Polymers have emerged as powerful biological tools; however, their ability to gain access to the intracellular environment is limited. To expand the biological utility of polymer scaffolds, we have synthesized an internalization domain using the ring-opening metathesis polymerization (ROMP). A polymer functionalized with guanidinium groups is effectively internalized by cells and localized in both vesicles and the cytoplasm. Because the synthesis of such materials is modular, we anticipate that compounds of this type can be fashioned that facilitate the delivery of cargo via end-cap derivatization or block copolymer synthesis.

MeSH Terms
Biomimetic Materials/chemical synthesis,metabolism Cytoplasmic Vesicles/chemistry,metabolism Glycosaminoglycans/chemistry,metabolism Guanidine/chemistry HeLa Cells/metabolism Humans Intracellular Membranes/chemistry,metabolism Magnetic Resonance Spectroscopy Microscopy, Confocal Oligopeptides/chemical synthesis,metabolism Permeability Receptors, Cell Surface/chemistry,metabolism
Chemicals
Glycosaminoglycans Oligopeptides Receptors, Cell Surface Guanidine
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Kolonko Erin M
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Kiessling Laura L
References (35)
35 references, click to expand
  1. A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile.
    Angew Chem Int Ed Engl. 2002 Nov 4;41(21):4035-7 PMID: 12412073
  2. Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts.
    Angew Chem Int Ed Engl. 2003 Oct 6;42(38):4592-633 PMID: 14533149
  3. Arginine-rich peptides. An abundant source of membrane-permeable peptides having potential as carriers for intracellular protein delivery.
    J Biol Chem. 2001 Feb 23;276(8):5836-40 PMID: 11084031
  4. Synthesis of end-labeled multivalent ligands for exploring cell-surface-receptor-ligand interactions.
    Chem Biol. 2000 Jan;7(1):9-16 PMID: 10662681
  5. Cell penetrating peptides in drug delivery.
    Pharm Res. 2004 Mar;21(3):389-93 PMID: 15070086
  6. Solid-phase synthesis, bioconjugation, and toxicology of novel cationic oligopeptoids for cellular drug delivery.
    Bioconjug Chem. 2007 Mar-Apr;18(2):342-54 PMID: 17326607
  7. Internalization of HIV-1 tat requires cell surface heparan sulfate proteoglycans.
    J Biol Chem. 2001 Feb 2;276(5):3254-61 PMID: 11024024
  8. Cell-surface proteoglycans as molecular portals for cationic peptide and polymer entry into cells.
    Biochem Soc Trans. 2007 Aug;35(Pt 4):788-93 PMID: 17635149
  9. Contrast agents for magnetic resonance imaging synthesized with ring-opening metathesis polymerization.
    J Am Chem Soc. 2006 May 24;128(20):6534-5 PMID: 16704234
  10. New hydrazone derivatives of adriamycin and their immunoconjugates--a correlation between acid stability and cytotoxicity.
    Bioconjug Chem. 1991 May-Jun;2(3):133-41 PMID: 1932212
  11. Molecular transporters: synthesis of oligoguanidinium transporters and their application to drug delivery and real-time imaging.
    Chembiochem. 2006 Oct;7(10):1497-515 PMID: 16972294
  12. The dawning era of polymer therapeutics.
    Nat Rev Drug Discov. 2003 May;2(5):347-60 PMID: 12750738
  13. TAT-mediated endocytotic delivery of the loop deletion Bcl-2 protein protects neurons against cell death.
    J Neurochem. 2005 Oct;95(1):230-43 PMID: 16181427
  14. Romping the cellular landscape: linear scaffolds for molecular recognition.
    Curr Opin Struct Biol. 2006 Aug;16(4):544-50 PMID: 16781140
  15. Protection against ischemic brain injury by protein therapeutics.
    Proc Natl Acad Sci U S A. 2002 Dec 24;99(26):17107-12 PMID: 12475933
  16. The convergence of synthetic organic and polymer chemistries.
    Science. 2005 Aug 19;309(5738):1200-5 PMID: 16109874
  17. Characterization of the pH of folate receptor-containing endosomes and the rate of hydrolysis of internalized acid-labile folate-drug conjugates.
    J Pharmacol Exp Ther. 2007 May;321(2):462-8 PMID: 17289839
  18. Dendritic molecular transporters provide control of delivery to intracellular compartments.
    Bioconjug Chem. 2007 Mar-Apr;18(2):403-9 PMID: 17284011
  19. Arginine-rich cell penetrating peptides: from endosomal uptake to nuclear delivery.
    Cell Mol Life Sci. 2005 Dec;62(23):2739-49 PMID: 16231085
  20. A comprehensive model for the cellular uptake of cationic cell-penetrating peptides.
    Traffic. 2007 Jul;8(7):848-66 PMID: 17587406
  21. Spanning binding sites on allosteric proteins with polymer-linked ligand dimers.
    Nature. 1998 Oct 15;395(6703):710-3 PMID: 9790193
  22. Cell-penetrating peptides. A reevaluation of the mechanism of cellular uptake.
    J Biol Chem. 2003 Jan 3;278(1):585-90 PMID: 12411431
  23. Intrinsically cell-permeable miniature proteins based on a minimal cationic PPII motif.
    J Am Chem Soc. 2007 Nov 28;129(47):14578-9 PMID: 17983240
  24. Solid-phase synthesis of polymers using the ring-opening metathesis polymerization.
    J Am Chem Soc. 2005 Oct 26;127(42):14536-7 PMID: 16231882
  25. Synthesis and applications of end-labeled neoglycopolymers.
    Org Lett. 2002 Jul 11;4(14):2293-6 PMID: 12098230
  26. Translocation of a beta-peptide across cell membranes.
    J Am Chem Soc. 2002 Jan 23;124(3):368-9 PMID: 11792194
  27. Conjugation of arginine oligomers to cyclosporin A facilitates topical delivery and inhibition of inflammation.
    Nat Med. 2000 Nov;6(11):1253-7 PMID: 11062537
  28. Synthesis of a multivalent display of a CD22-binding trisaccharide.
    Carbohydr Res. 2002 Oct 8;337(18):1605-13 PMID: 12423961
  29. Cellular uptake of arginine-rich peptides: roles for macropinocytosis and actin rearrangement.
    Mol Ther. 2004 Dec;10(6):1011-22 PMID: 15564133
  30. Small-molecule mimics of an alpha-helix for efficient transport of proteins into cells.
    Nat Methods. 2007 Feb;4(2):153-9 PMID: 17220893
  31. Designing materials for biology and medicine.
    Nature. 2004 Apr 1;428(6982):487-92 PMID: 15057821
  32. Pathway for polyarginine entry into mammalian cells.
    Biochemistry. 2004 Mar 9;43(9):2438-44 PMID: 14992581
  33. Trivalent ligands with rigid DNA spacers reveal structural requirements for IgE receptor signaling in RBL mast cells.
    ACS Chem Biol. 2007 Oct 19;2(10):674-84 PMID: 18041817
  34. Oligoarginine vectors for intracellular delivery: design and cellular-uptake mechanisms.
    Biopolymers. 2006;84(3):241-9 PMID: 16333858
  35. Synthetic multivalent ligands as probes of signal transduction.
    Angew Chem Int Ed Engl. 2006 Apr 3;45(15):2348-68 PMID: 16557636
Article Info
Journal
Journal of the American Chemical Society
Abbr.
J Am Chem Soc
ISSN
1520-5126
DOI
10.1021/ja8001716
Published
2008-04-30
Epub
2008-00-08
Pages
5626-7
Language
English
Region
United States
NLM ID
7503056
PMCID
PMC3216674
Subset
IM
Grants
NIGMS NIH HHS · T32 GM008505 · United States
NIGMS NIH HHS · GM008505 · United States
NCRR NIH HHS · S10 RR013866 · United States
NIGMS NIH HHS · R29 GM049975 · United States
NIGMS NIH HHS · R01 GM049975 · United States
NIGMS NIH HHS · R01 GM049975-15 · United States
NCRR NIH HHS · 1 S10 RR13866-01 · United States
NIGMS NIH HHS · GM49975 · United States
NIGMS NIH HHS · T32 GM008505-17 · United States
External Links
PubMed source DOI: 10.1021/ja8001716 PMC Full Text View journal details
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