The intracellular pharmacokinetics of terminally capped peptides

Molecular Pharmaceutics

Volumn 9, Issue 5, 2012, Pages 1077-1086

  Ruttekolk, Ivo R ^a   Witsenburg, J Joris ^a   Glauner, Heike ^a   Bovee Geurts, Petra H M ^a   Ferro, Emer S ^b   Verdurmen, Wouter P R ^a   Brock, Roland ^a  

^a RADBOUD UNIVERSITY MEDICAL CENTER   (Netherlands)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

drug delivery; electroporation; fluorescence correlation spectroscopy; intracellular peptide therapeutics; peptidomimetics; Proteolysis; synthetic peptides

Indexed keywords

CD3ZPY72 PEPTIDE; FLUORESCEIN; GAB2 S09 PEPTIDE; GAB2PY614 PEPTIDE; LATPY132 PEPTIDE; LATPY191 PEPTIDE; LATPY226 PEPTIDE; P21 ACTIVATED KINASE 1; PEPTIDE; PROTEIN SH2; PROTEIN SH3; SLP179 PEPTIDE; SLP228 PEPTIDE; TERMINALLY CAPPED PEPTIDE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; CELLULAR DISTRIBUTION; CELLULAR PARAMETERS; CONTROLLED STUDY; ELECTROPORATION; FLUORESCENCE; HALF LIFE TIME; HYDROPHOBICITY; INTRACELLULAR RESIDENCE TIME; LEUKEMIA CELL LINE; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN DOMAIN; PROTEIN LOCALIZATION; PROTEIN STABILITY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; CELL LINE; ELECTROPORATION; FLOW CYTOMETRY; FLUORESCENCE; HUMANS; MODELS, THEORETICAL; MOLECULAR SEQUENCE DATA; PEPTIDES; PEPTIDOMIMETICS; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84860738471     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp200331g     Document Type: Article

References (37)

1. Pawson, T.; Nash, P. Assembly of cell regulatory systems through protein interaction domains Science 2003, 300, 445-452
2. Jarver, P.; Mager, I.; Langel, U. In vivo biodistribution and efficacy of peptide mediated delivery Trends Pharmacol. Sci. 2010, 31, 528-535
3. Bates, E.; Bode, C.; Costa, M.; Gibson, C. M.; Granger, C.; Green, C.; Grimes, K.; Harrington, R.; Huber, K.; Kleiman, N.; Mochly-Rosen, D.; Roe, M.; Sadowski, Z.; Solomon, S.; Widimsky, P. Intracoronary KAI-9803 as an adjunct to primary percutaneous coronary intervention for acute ST-segment elevation myocardial infarction Circulation 2008, 117, 886-896
4. Souroujon, M. C.; Mochly-Rosen, D. Peptide modulators of protein-protein interactions in intracellular signaling Nat. Biotechnol. 1998, 16, 919-924
5. Yaffe, M. B. Phosphotyrosine-binding domains in signal transduction Nat. Rev. Mol. Cell Biol. 2002, 3, 177-186
6. Li, S. S. Specificity and versatility of SH3 and other proline-recognition domains: structural basis and implications for cellular signal transduction Biochem. J. 2005, 390, 641-653
7. Ranganathan, R.; Ross, E. M. PDZ domain proteins: Scaffolds for signaling complexes Curr. Biol. 1997, 7, R770-R773
8. Stoevesandt, O.; Kohler, K.; Fischer, R.; Johnston, I. C.; Brock, R. One-step analysis of protein complexes in microliters of cell lysate Nat. Methods 2005, 2, 833-835
9. Jung, G.; Beck-Sickinger, A. G. Multiple peptide synthesis methods and their applications Angew. Chem., Int. Ed. 1992, 31, 367-383
10. Beutling, U.; Stading, K.; Stradal, T.; Frank, R. Large-scale analysis of protein-protein interactions using cellulose-bound peptide arrays Adv. Biochem. Eng. Biotechnol. 2008, 110, 115-152
11. Salisbury, C. M.; Maly, D. J.; Ellman, J. A. Peptide microarrays for the determination of protease substrate specificity J. Am. Chem. Soc. 2002, 124, 14868-14870
12. Stoevesandt, O.; Kohler, K.; Wolf, S.; Andre, T.; Hummel, W.; Brock, R. A network analysis of changes in molecular interactions in cellular signaling Mol. Cell Proteomics 2007, 6, 503-513
13. Qvit, N.; Mochly-Rosen, D. Highly Specific Modulators of Protein Kinase C Localization: Applications to Heart Failure Drug Discovery Today: Dis. Mech. 2010, 7, e87-e93
14. Budas, G. R.; Disatnik, M. H.; Mochly-Rosen, D. Aldehyde dehydrogenase 2 in cardiac protection: A new therapeutic target? Trends Cardiovasc. Med. 2009, 19, 158-164
15. Reits, E.; Griekspoor, A.; Neijssen, J.; Groothuis, T.; Jalink, K.; van Veelen, P.; Janssen, H.; Calafat, J.; Drijfhout, J. W.; Neefjes, J. Peptide diffusion, protection, and degradation in nuclear and cytoplasmic compartments before antigen presentation by MHC class I Immunity 2003, 18, 97-108
16. Cunha, F. M.; Berti, D. A.; Ferreira, Z. S.; Klitzke, C. F.; Markus, R. P.; Ferro, E. S. Intracellular peptides as natural regulators of cell signaling J. Biol. Chem. 2008, 283, 24448-24459
17. Berti, D. A.; Morano, C.; Russo, L. C.; Castro, L. M.; Cunha, F. M.; Zhang, X.; Sironi, J.; Klitzke, C. F.; Ferro, E. S.; Fricker, L. D. Analysis of intracellular substrates and products of thimet oligopeptidase in human embryonic kidney 293 cells J. Biol. Chem. 2009, 284, 14105-14116
18. Brinckerhoff, L. H.; Kalashnikov, V. V.; Thompson, L. W.; Yamshchikov, G. V.; Pierce, R. A.; Galavotti, H. S.; Engelhard, V. H.; Slingluff, C. L., Jr. Terminal modifications inhibit proteolytic degradation of an immunogenic MART-1(27-35) peptide: implications for peptide vaccines Int. J. Cancer 1999, 83, 326-334
19. Fischer, R.; Bächle, D.; Fotin-Mleczek, M.; Jung, G.; Kalbacher, H.; Brock, R. A targeted protease substrate for a quantitative determination of proteolytic activities in the endolysosomal pathway ChemBioChem 2006, 7, 1428-1434
20. Gehl, J. Electroporation: Theory and methods, perspectives for drug delivery, gene therapy and research Acta Physiol. Scand. 2003, 177, 437-447
21. Knight, D. E.; Scrutton, M. C. Gaining access to the cytosol: the technique and some applications of electropermeabilization Biochem. J. 1986, 234, 497-506
22. Fotin-Mleczek, M.; Welte, S.; Mader, O.; Duchardt, F.; Fischer, R.; Hufnagel, H.; Scheurich, P.; Brock, R. Cationic cell-penetrating peptides interfere with TNF signaling by induction of TNF receptor internalization J. Cell Sci. 2005, 118, 3339-3351
23. Chorev, M.; Shavitz, R.; Goodman, M.; Minick, S.; Guillemin, R. Partially modified retro-inverso-enkephalinamides: Topochemical long-acting analogs in vitro and in vivo Science 1979, 204, 1210-1212
24. Fischer, P. M. The design, synthesis and application of stereochemical and directional peptide isomers: A critical review Curr. Protein Pept. Sci. 2003, 4, 339-356
25. Rigler, R.; Mets, Ü.; Widengren, J.; Kask, P. Fluorescence correlation spectroscopy with high count rate and low background: Analysis of translational diffusion Eur. Biophys. J. 1993, 22, 169-175
26. Bartels, M.; Schweda, A. T.; Dreikhausen, U.; Frank, R.; Resch, K.; Beil, W.; Nourbakhsh, M. Peptide-mediated disruption of NFkappaB/NRF interaction inhibits IL-8 gene activation by IL-1 or Helicobacter pylori J. Immunol. 2007, 179, 7605-7613
27. Ruttekolk, I. R.; Verdurmen, W. P.; Chung, Y. D.; Brock, R. Measurements of the intracellular stability of CPPs Methods Mol. Biol. 2011, 683, 69-80
28. Fischer, R.; Waizenegger, T.; Köhler, K.; Brock, R. A quantitative validation of fluorophore-labelled cell-permeable peptide conjugates: Fluorophore and cargo dependence of import Biochim. Biophys. Acta, Biomembr. 2002, 1564, 365-374
29. Reits, E.; Neijssen, J.; Herberts, C.; Benckhuijsen, W.; Janssen, L.; Drijfhout, J. W.; Neefjes, J. A major role for TPPII in trimming proteasomal degradation products for MHC class I antigen presentation Immunity 2004, 20, 495-506
30. Chuang, C. K.; Rockel, B.; Seyit, G.; Walian, P. J.; Schonegge, A. M.; Peters, J.; Zwart, P. H.; Baumeister, W.; Jap, B. K. Hybrid molecular structure of the giant protease tripeptidyl peptidase II Nat. Struct. Mol. Biol. 2010, 17, 990-996
31. Saric, T.; Graef, C. I.; Goldberg, A. L. Pathway for degradation of peptides generated by proteasomes: A key role for thimet oligopeptidase and other metallopeptidases J. Biol. Chem. 2004, 279, 46723-46732
32. Oliveira, V.; Campos, M.; Melo, R. L.; Ferro, E. S.; Camargo, A. C.; Juliano, M. A.; Juliano, L. Substrate specificity characterization of recombinant metallo oligo-peptidases thimet oligopeptidase and neurolysin Biochemistry 2001, 40, 4417-4425
33. Rock, K. L.; York, I. A.; Goldberg, A. L. Post-proteasomal antigen processing for major histocompatibility complex class I presentation Nat. Immunol. 2004, 5, 670-677
34. Gelman, J. S.; Sironi, J.; Castro, L. M.; Ferro, E. S.; Fricker, L. D. Peptidomic analysis of human cell lines J. Proteome Res. 2011, 10, 1583-1592
35. Paz, P.; Brouwenstijn, N.; Perry, R.; Shastri, N. Discrete proteolytic intermediates in the MHC class I antigen processing pathway and MHC I-dependent peptide trimming in the ER Immunity 1999, 11, 241-251
36. Machado, M. F.; Cunha, F. M.; Berti, D. A.; Heimann, A. S.; Klitzke, C. F.; Rioli, V.; Oliveira, V.; Ferro, E. S. Substrate phosphorylation affects degradation and interaction to endopeptidase 24.15, neurolysin, and angiotensin-converting enzyme Biochem. Biophys. Res. Commun. 2006, 339, 520-525
37. Fischer, R.; Hufnagel, H.; Brock, R. A doubly labeled penetratin analogue as a ratiometric sensor for intracellular proteolytic stability Bioconjugate Chem. 2010, 21, 64-73