Glycosylated cell-penetrating peptides and their conjugates to a proapoptotic peptide: Preparation by click chemistry and cell viability studies

Journal of Chemical Biology

Volumn 3, Issue 2, 2010, Pages 51-65

  Dutot, Laurence ^a   Lécorché, Pascaline ^a   Burlina, Fabienne ^a   Marquant, Rodrigue ^a   Point, Vanessa ^a   Sagan, Sandrine ^a   Chassaing, Gérard ^a   Mallet, Jean Maurice ^b   Lavielle, Solange ^a  

^a CNRS   (France)

^b Centre National de la Recherche Scientifique   (France)

Author keywords

Apoptose; Cell penetrating peptide; Click chemistry; Glycosylation; Triazole

Indexed keywords

ARGINYLARGINYLTRYPTOPHYLTRYPTOPHYLARGINYLARGINYLTRYPTOPHYLARGINYLARGININE; CELL PENETRATING PEPTIDE; GALACTOSE; LYSYLLEUCYLALANYLLYSYLLEUCYLALANYLLYSYLLYSYLLEUCYLALANYLLYSYLLEUCYLALANYLLYSINE; MEMBRANE PROTEIN; PENETRATIN; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL SPECIFICITY; CELL TRANSPORT; CELL VIABILITY; CELLULAR DISTRIBUTION; CHEMICAL REACTION; CHO CELL; CONJUGATE; CONTROLLED STUDY; DISULFIDE BOND; GLYCOSYLATION; INTERNALIZATION; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; SEQUENCE ANALYSIS; SOLID;

EID: 77954564961     PISSN: 18646158     EISSN: 18646166     Source Type: Journal    
DOI: 10.1007/s12154-009-0031-9     Document Type: Article

References (60)

1. Alberts B, Johnson A, Lewis J, Raff M, Roberts K, Walter P (2008) Molecular biology of the cell. Garland Publishing Inc, New York
2. Rubertalli A, Sitia R (1995) Entry of exogenous polypeptides into the nucleus of living cells: facts and speculations. Trends Cell Biol 5:409-412
3. Dietz GPH, Bähr M (2004) Delivery of bioactive molecules into the cell: the Trojan horse approach. Mol Cell Neurosci 27:85-131
4. Langel U (ed) (2007) In: Handbook of Cell-Penetrating Peptides, 2nd edn. Taylor and Francis, Boca Raton
5. Morris MC, Deshayes S, Heitz F, Divita G (2008) Cell-penetrating peptides: from molecular mechanisms to therapeutics. Biol Cell 100:201-217
6. Hansen M, Kilk K, Langel U (2008) Predicting cell-penetrating peptides. Adv Drug Deliv Rev 60:572-579
7. Derossi D, Joliot AH, Chassaing G, Prochiantz A (1994) The third helix of the Antennapedia homeodomain translocates through biological membranes. J Biol Chem 269:10444-11045
8. Vivès E, Brodin P, Lebleu B (1997) A truncated HIV-1 Tat protein basic domain rapidly translocates through the plasma membrane and accumulates in the cell nucleus. J Biol Chem 272:16010-16017
9. Dom G, Shaw-Kackson C, Matis C, Bouffioux O, Picard JJ, Prochiantz A, Mingeot-Leclercq MP, Brasseur R, Rezsohazy R (2003) Cellular uptake of Antennapedia Penetratin peptides is a two-step process in which phase transfer precedes a tryptophandependent translocation. Nucleic Acid Res 31:556-561
10. Fischer R, Fotin-Mleczek M, Hufnagel H, Brock R (2005) Break on through to the other side - biophysics and cell biology shed light on cell-penetrating peptides. ChemBioChem 6:2126-2142
11. Lundin P, Johansson H, Guterstam P, Holm T, Hansen M, Langel U (2008) Distinct uptake routes of cell-penetrating peptide conjugates. El Andaloussi S. Bioconj Chem 19:2535-2542
12. Duchardt F, Fotin-Mleczek M, Schwarz H, Fischer R, Brock R (2007) A comprehensive model for the cellular uptake of cationic cell-penetrating peptides. Traffic 8:848-866
13. Vives E, Schmidt J, Pelegrin A (2008) Cell-penetrating and celltargeting peptides in drug delivery. Biochim Biophys Acta 1786:126-138
14. Watkins CL, Schmaljohann D, Futaki S, Jones AT (2009) Low concentration thresholds of plasma membranes for rapid energyindependent translocation of a cell-penetrating peptide. Biochem J 420:179-189
15. Jiao CY, Delaroche D, Burlina F, Alves ID, Chassaing G, Sagan S (2009) Translocation and endocytosis for cell-penetrating peptides (CPP) internalization. J Biol Chem (in press)
16. Crombez L, Aldrian-Herrada G, Konate K, Nguyen QN, McMaster GK, Brasseur R, Heitz F, Divita G (2008) A new potent secondary amphipathic cell-penetrating peptide for siRNA delivery into mammalian cells. Molec Ther 17:95-103
17. Enback J, Laakkonen P (2007) Tumour-homing peptides: tools for targeting, imaging and destruction. Biochem Soc Trans 35: 780-783
18. Aussedat B, Dupont E, Sagan S, Joliot AH, Lavielle S, Chassaing G, Burlina F (2008) Modifications in the chemical structure of Trojan carriers: impact on cargo delivery. Chem Commun 1398-1400
19. Derossi D, Chassaing G, Prochiantz A (1998) Trojan peptides: the penetratin system for intracellular delivery. Trends Cell Biol 8:84-87
20. Delaroche D, Aussedat B, Aubry S, Chassaing G, Burlina F, Clodic G, Bolbach G, Lavielle S, Sagan S (2007) Tracking a new cell-penetrating (W/R) nonapeptide, through an enzyme-stable mass spectrometry reporter tag. Anal Chem 79:1932-1938
21. Chassaing G, Prochiantz A (1997) Peptides usable as vectors for the intracellular addressing of bioactive molecules. PCT Int Appl WO 9712912 A1 19970410
22. Lavielle S, Ling N, Guillemin R (1981) Solid-phase synthesis of two glycopeptides containing the amino acid sequence 5 to 9 of somatostatin. Carbohydrate Res 89:221-228
23. Polt R, Porreca F, Szabo LZ, Bilsky EJ, Davis P, Abbruscato TJ, Davis TP, Horvath R, Yamamura HI, Hruby VJ (1994) Glycopeptide enkephalin analogues produce analgesia in mice: evidence for penetration of the blood-brain barrier. Proc Natl Acad Sci USA 91:7114-7118
24. Michael K, Wittmann V, König W, Sandow J, Kessler HS (1996) S- and C-glycopeptide derivatives of an LH-RH antagonist. Int J Peptide Protein Res 48:59-70
25. Egleton RD, Mitchell SA, Huber JD, Janders J, Stropova D, Polt R, Yamamura HI, Hruby VJ, Davis TP (2005) Biousian glycopeptides penetrate the blood-brain barrier. Tetrahedron Asymmetry 16:65-75
26. Foerg C, Ziegler U, Fernandez-Carneado J, Giralt E, Rennert R, Beck-Sickinger AG, Merkle HP (2005) Decoding the entry of two novel cell-penetrating peptides in HeLa cells: lipid raft-mediated endocytosis and endosomal escape. Biochemistry 44:72-81
27. Magzoub M, Pramanik A, Graslund A (2005) Modeling the endosomal escape of cell-penetrating peptides: transmembrane pH gradient driven translocation across phospholipid bilayers. Biochemistry 44:14890-14897
28. Shiraishi T, Nielsen PE (2006) Enhanced delivery of cellpenetrating peptide-peptide nucleic acid conjugates by endosomal disruption. Nat Protoc 1:633-636
29. Lundberg P, El-Andaloussi S, Sutlu T, Johansson H, Langel U (2007) Delivery of short interfering RNA using endosomolytic cell-penetrating peptides. FASEB J 21:2664-2671
30. Lo SL, Wang S (2008) An endosomolytic Tat peptide produced by incorporation of histidine and cysteine residues as a nonviral vector for DNA transfection. Biomaterials 29:2408-2414
31. Law B, Quinti L, Choi Y, Weissleder R, Tung CH (2006) A mitochodrial targeted fusion peptide exhibits remarkable cytotoxicity. Mol Cancer Ther 5:1944-1949
32. Foillard S, Jin ZH, Garanger E, Boturyn D, Favrot MC, Coll JL, Dumy P (2008) Synthesis and biological characterisation of targeted pro-apoptotic peptide. Chem Bio Chem 9:2326-2332
33. Marks AJ, Cooper MS, Anderson RJ, Orchard KH, Hale G, North JM, Ganeshaguru K, Steele AJ, Mehta AB, Lowdell MW, Wickremasinghe RG (2005) Selective apoptotic killing of malignant hemopoietic cells by antibody-targeted delivery of an amphipathic peptide. Cancer Res 65:2373-2377
34. Collot M, Savreux J, Mallet JM (2008) New thioglycoside derivatives for use in odorless synthesis of MUXF3 N-glycan fragments related to food allergens. Tetrahedron 64:1523-1535
35. Joosten JAF, Loimaranta V, Appeldoorn CCM, Haataja S, El Maate FA, Liskamp RMJ, Finne J, Pieters RJ (2004) Inhibition of streptococcus suis adhesion by dendritic galabiose compounds at low nanomolar concentration. J Med Chem 47:6499-6508
36. Zhu X, Kawatkar S, Rao Y, Boons GJ (2006) Practical approach for the stereoselective introductionof b-arabinofuranosides. J Am Chem Soc 129:11948-11957
37. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004-2021
38. Tornoe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 67:3057-3064
39. Zhang Z, Fan E (2006) Solid phase synthesis of peptidotriazoles with multiple cycles of triazole formation. Tetrahedron Lett 47:665-669
40. Jang H, Fafarman A, Holub JM, Kirshenbaum K (2005) Click to fit: versatile polyvalent display on a peptidomimetic scaffold. Org Lett 7:1951-1954
41. Coats SJ, Link JS, Gauthier D, Hlasta DJ (2005) Trimethylsilyldirected 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles. Org Lett 7:1469-1472
42. Harju K, Vahermo M, Mutikainen I, Yli-Kauhaluoma J (2003) Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition. J Comb Chem 5:826-833
43. Parikh PB, Kim YS, Chang YT (2002) Single resin bead kinetics using real time fluorescence measurements. Bull Korean Chem Soc 23:1509-1510
44. Ploux O, Chassaing G, Marquet A (1987) Cyclization of peptides on a solid support - Application to cyclic analogs of substance-P. Int J of Peptide and Protein Res 29:162-169
45. Aubry S, Burlina F, Dupont E, Delaroche D, Joliot A, Lavielle S, Chassaing G, Sagan S (2009) Cell-surface thiols affect cell entry of disulfide-conjugated peptides. FASEB J (in press)
46. Burlina F, Sagan S, Bolbach G, Chassaing G (2005) Quantification of the cellular uptake of cell-penetrating peptides by MALDITOF mass spectrometry. Angew Chem Int Ed 44:4244-4247
47. Richard JP, Melikov K, Vives E, Ramos C, Verbeure B, Gait MJ, Chernomordik LV, Lebleu B (2003) Cell-penetrating peptides - A reevaluation of the mechanism of cellular uptake. J Biol Chem 278:585-590
48. Puckett CA, Barton JK (2009) Fluorescein redirects a rutheniumoctaarginine conjugate to the nucleus. J Am Chem Soc 131: 8738-8739
49. Dupont E, Prochiantz A, Joliot A (2007) Identification of a signal peptide for unconventional secretion. J Biol Chem 282: 8994-9000
50. Wender PA, Mitchell DJ, Pattabiraman K, Pelkey ET, Steinman L, Rothbard JB (2000) The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters. Proc Natl Acad Sci USA 97:13003-13008
51. Mitchell DJ, Kim DT, Steinman L, Fathman CG, Rothbard JB (2000) Polyarginine enters cells more efficiently than other polycationic homopolymers. J Pept Res 56:318-325
52. Rothbard B, Kreider E, VanDeusen CL, Wright L, Wylie BL, Wender PA (2002) Arginine-rich molecular transporters for drug delivery: role of backbone spacing in cellular uptake. J Med Chem 45:3612-3618
53. Bilsky EJ, Egleton RD, Mitchell SA, Palian MM, Davis P, Huber JD, Jones H, Yamamura HI, Janders J, Davis TP, Porreca F, Hruby VJ, Polt R (2000) Enkephalin glycopeptide analogues produce analgesia with reduced dependence liability. J Med Chem 43:2586-2590
54. Buskas T, Ingale S, Boons GJ (2006) Glycopeptides as versatile tools for glycobiology. Glycobiology 16:113R-136R
55. Maiti KK, Lee WS, Takeuchi T, Watkins C, Fretz M, Kim DC, Futaki S, Jones A, Kim KT, Chung SK (2007) Guanidinecontaining molecular transporters: sorbitol-based transporters show high intracellular selectivity toward mitochondria. Angew Chem Int Ed 46:5880-5884
56. Maiti KK, Jeon OY, Lee WS, Chung SK (2007) Design, synthesis, and delivery properties of novel guanidine-containing molecular transporters built on dimeric inositol scaffolds. Chem Eur J 13:762-775
57. Yu H, Chokhawala H, Karpel R, Yu H, Wu B, Zhang J, Zhang Y, Jia Q, Chen X (2005) A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries. J Am Chem Soc 127:17618-17619
58. Liu XM, Thakur A, Wang D (2007) Efficient synthesis of linear multifunctional poly(ethylene glycol) by copper(I)-catalyzed huisgen 1,3-dipolar cycloaddition. Biomacromol 8:2653-2658
59. Sachon E, Tasseau O, Lavielle S, Sagan S, Bolbach G (2003) Isotope and affinity tags in photoreactive substance P analogues to identify the covalent linkage within the NK-1 receptor by MALDI-TOF analysis. Anal Chem 75:6536-6543
60. Hasegawa T, Numata M, Okumura S, Kimura T, Sakurai K, Shinkai S (2007) Carbohydrateappended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins. Org Biomol Chem 5:2404-2412