Primary amphipathic cell-penetrating peptides: Structural requirements and interactions with model membranes

Biochemistry

Volumn 43, Issue 24, 2004, Pages 7698-7706

  Deshayes, Sébastien ^a   Plénat, Thomas ^b   Aldrian Herrada, Gudrun ^a   Divita, Gilles ^a   Le Grimellec, Christian ^b   Heitz, Frédéric ^a  

^a Centre National de la Recherche Scientifique   (France)

^b CENTRE DE BIOCHIMIE STRUCTURALE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC FORCE MICROSCOPY; CELLS; CONFORMATIONS; MOLECULAR STRUCTURE; PHOSPHOLIPIDS; POLYPEPTIDES;

CELL PENETRATING PEPTIDES;

BIOCHEMICAL ENGINEERING;

PEPTIDE P ALPHA; PEPTIDE P BETA; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CELL INVASION; CELL MEMBRANE TRANSPORT; CONFORMATIONAL TRANSITION; DRUG DELIVERY SYSTEM; DRUG SYNTHESIS; DRUG UPTAKE; MEMBRANE BINDING; MEMBRANE STRUCTURE; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN INTERACTION; PROTEIN LIPID INTERACTION; PROTEIN STRUCTURE;

ADSORPTION; AMINO ACID SEQUENCE; CIRCULAR DICHROISM; MEMBRANES, ARTIFICIAL; MICROSCOPY, ATOMIC FORCE; MOLECULAR SEQUENCE DATA; PEPTIDES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 2942715203     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi049298m     Document Type: Article

References (45)

1. Mahato, R. I. (1997) Nonviral peptide-based approaches to gene delivery. J. Drug Targeting 7, 249-268.
2. Morris, M. C., Chaloin, L., Heitz, F., and Divita, G. (2000) Translocating peptides and proteins and their use for gene delivery. Curr. Opin. Biotechnol. 11, 461-466.
3. Gariépy, J., and Kawamura, K. (2001) Vectorial delivery of macromolecules into cells using peptide-based vehicles. Trends Biotechnol. 19, 21-28.
4. Rittner, K., Benavente, A., Bompard-Sorlet, A., Heitz, F., Divita, G., Brasseur, R., and Jacobs, E. (2002) New basic membrane-destabilizing peptides for plasmid-based gene delivery in vitro and in vivo. Mol. Ther. 5, 104-114.
5. Wadia, J. S., and Dowdy, S. F. (2002) Protein transduction technology. Curr. Opin. Biotechnol. 13, 52-56.
6. Dom, G., Show-Jackson, C., Matis, C., Bouffioux, O., Picard, J. J., Prochiantz, A., Mingeot-Leclercq, M. P., Brasseur, R., and Rezsohazy, R. (2003) Cellular uptake of Antennapedia Penetratin peptides is a two-step process in which phase transfer precedes a tryptophan-dependent translocation. Nucleic Acids Res. 31, 556-561.
7. Schwarze, S. R., Ho, A., Vocero-Akbani, A., ans Dowdy, S. F. (1999) In vivo protein transduction: delivery of a biologically active protein into the mouse. Science 285, 1569-1572.
8. Dathe, M., and Wieprecht, T. (1999) Structural features of helical antimicrobial peptides: their potential to modulate activity on model membranes and biological cells. Biochim. Biophys. Acta 1462, 71-87.
9. Oehlke, J., Scheller, A., Wiesner, B., Krause, E., Beyermann, M., Klauschenz, E., Melzig, M., and Bienert, M. (1998) Cellular uptake of an α-helical amphipathic model peptide with the potential to deliver polar compounds into the cell interior nonendocytically. Biochim. Biophys. Acta 1414, 127-139.
10. Vivès, E., Brodin, P., and 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.
11. Wyman, T. B., Nicol, F., Zelphati, O., Scaria, P. V., Plank, C., and Szoka, F. C., Jr. (1997) Design, synthesis, and characterization of a cationic peptide that binds to nucleic acids and permeabilizes bilayers. Biochemistry 36, 3008-3017.
12. Lindgren, M., Gallet, X., Soomets, U., Hallbrink, M., Brakenhielm, E., Pooga, M., Brasseur, R., and Langel, Ü. (2000) Translocation properties of novel cell penetrating transportan and penetratin analogues. Bioconjug. Chem. 11, 619-626.
13. Rudolph, C., Plank, C., Lausier, J., Schillinger, U., Muller, R. H., and Rosenecker, J. (2003) Oligomers of the arginine-rich motif of the HIV-1 TAT protein are capable of transferring plasmid DNA into cells. J Biol Chem. 278, 11411-11418.
14. Leonetti, J. P., Degols, G., and Lebleu, B. (1990) Biological activity of oligonucleotide-poly(L-lysine) conjugates: mechanism of cell uptake. Bioconjug. Chem. 1, 149-153.
15. Futaki, S., Suzuki, T., Ohashi, W., Yagami, T., Tanaka, S., Ueda, K., and Sigiura, Y. (2001) Arginine-rich peptides. An abundant source of membrane-permeable peptides having potential as carriers for intracellular protein delivery. J. Biol. Chem. 276, 5836-5840.
16. Briggs, M. S., and Gierasch, L. M. (1986) Molecular mechanisms of protein secretion: the role of the signal sequence. Adv. Protein Chem. 38, 109-180.
17. Slepushkin, V. A., Andreev, S. M., Sidorova, M. V., Melikyan, G. B., Grigoriev, V. B., Chumakov, V. M., Grinfeldt, A. E., Manukyan, R. A., and Karamov, E. V. (1992) Investigation of human immunodeficiency virus fusion peptides. Analysis of interrelations between their structure and function. AIDS Res. Hum. Retroviruses 8, 9-18.
18. Goldfarb, D. S., Gariépy, J., Schoolnik, G., and Kornberg, R. D. (1986) Synthetic peptides as nuclear localization signals. Nature 322, 641-644.
19. Chaloin, L., Vidal, P., Heitz, A., Van Mau, N., Méry, J., Divita, G., and Heitz, F. (1997) Conformations of Primary Amphipathic Carrier Peptides in Membrane Mimicking Environments. Biochemistry 36, 11179-11187.
20. Chaloin, L., Vidal, P., Lory, P., Méry, J., Lautredou, N., Divita, G., and Heitz, F. (1998) Design of Carrier Peptide-Oligonucleotide Conjugate with Rapid Membrane Translocation and Nuclear Localization Properties. Biochim. Biophys. Res. Commun. 243, 601-608
21. Morris, M. C., Vidal, P., Chaloin, L., Heitz, F., and Divita, G. (1997) A new peptide vector for efficient delivery of oligonucleotide into nontransformed mammalian cells. Nucleic Acid Res. 25, 2730-2736.
22. Vidal, P., Chaloin, L., Heitz, A., Van Mau, N., Méry, J., Divita, G., and Heitz; F. (1998) Conformational Analysis of Primary Amphipathic Carrier Peptides and Origin of the Various Cellular Localizations. J. Membr. Biol. 162, 259-264.
23. Vidal, P., Chaloin, L., Méry, J., Lamb, N., Lautredou, N., Bennes, R., and Heitz, F. (1996) Solid-phase Synthesis and Cellular Localization of a C- and/or N-terminal Labeled Peptide. J. Pept. Sci. 2, 125-133.
24. Briggs, M. S., Cornell, D. G., Dluhy, R. A., and Gierasch, L. M. (1986) Conformations of signal peptides induced by lipids suggest initial steps in protein export. Science 233, 206-208.
25. Van Mau, N., Vié, V., Chaloin, L., Lesniewska, E., Heitz, F., and Le Grimellec, C. (1999) Lipid-Induced Organization of a Primary Amphipathic Peptide. A coupled AFM-Monolayer Study. J. Membr. Biol. 167, 241-249.
26. Munoz, V., and Serrano, L. (1997) Development of the multiple sequence approximation within the AGADIR model of alpha-helix formation: comparison with Zimm-Bragg and Lifson-Roig formalism. Biopolymers 41, 495-509.
27. Greenfield, N., and Fasman, G. D. (1969) Computed circular dichroism spectra for the evaluation of protein conformation. Biochemistry 8, 4108-4116.
28. Wu, Y., Huang, H. W., and Olah, G. A. (1990) Method of oriented circular dichroism. Biophys. J. 57, 797-806.
29. Vié, V., Van Mau, N., Chaloin, L., Lesniewska, E., Le Grimellec, C., and Heitz, F. (2000) Detection of Peptide - Lipid Interactions in Mixed Monolayers, Using Isotherms, Atomic Force Microscopy, and Fourier Transform Infrared Analyses. Biophys. J. 78, 846-856.
30. Arrondo, J. L., Muga, A., Castreana, J., and Goni, F. M. (1993) Quantitative studies of the structure of proteins in solution by Fourier transform infrared spectroscopy. Prog. Biophys. Mol. Biol. 59, 23-56.
31. Rafalski, M., Lear, J. D., and DeGrado, W. F. (1990) Phospholipid interactions of synthetic peptides representing the N-terminus of HIV gp41. Biochemistry 29, 7917-7922.
32. Maget-Dana, R. (1999) The monolayer technique: a potent tool for studying the interfacial properties of antimicrobial and membrane-lytic peptides and their interactions with lipid membranes. Biochim. Biophys. Acta 1462, 109-140.
33. Lakhdar-Ghazal, F., and Tocanne, J. F. (1981) Phase behaviour in monolayer and in water dispersions of mixtures of dimannosyldiacylglycerol with phosphatidylglycerol. Biochim. Biophys. Acta 644, 284-294.
34. Tamm, L. K., and McConnell, H. M. (1985) Supported phospholipid bilayers. Biophys. J. 47, 105-113.
35. Ruano, M. L., Nag, K., Worthman, L.-A., Casals, C., Pérez-Gil, J., and Keough, K. M. W. (1998) Differential partitioning of pulmonary surfactant protein SP-A into regions of monolayers of dipalmitoylphosphatidylcholine and dipalmitoylphosphatidylcholine/dipalmitoylphosphatidylglycerol. Biophys. J. 74, 1101-1109.
36. Crisp, D. J. (1949) A two-dimensional phase rule. I. Derivation of a two-dimensional phase rule for planar interface. II. Some applications of a two-dimensional phase rule for a single surface. In Surface Chemistry Butterworths, London, 17-35.
37. Gaines, G. L. (1966) Mixed monolayers. In Insoluble Monolayers at Liquid-Gas Interfaces. Prigogine, Ed. Interscience, New York, 281-300.
38. Taneva, S., and Keough, K. M. W. (1994) Pulmonary surfactant proteins SP-B and SP-C in spread monolayers at the air-water interface. I. Monolayers of pulmonary surfactant protein SP-B and phospholipids. Biophys. J. 66, 1137-1148.
39. Vié, V., Van Mau, N., Lesniewska, E., Goudonnet, J. P., Heitz, F., and Le Grimellec, C. (1998) Distribution of Ganglioside GM1 between Two-component, Two-phase Phosphatidylcholine Monolayers. Langmuir 14, 4574-4593.
40. Yuan, C., and Johnston, L. J. (2000) Distribution of ganglioside GM1 in L-α-dipalmitoylphosphatidylcholine/cholesterol monolayers: a model for lipid rafts, Biophys. J. 79, 2768-2781.
41. Demel, R. A., Geurts van Kessel, W. S., Zwaal, R. F., Roelofsen, B., and van Deenen, L. L., (1975) Relation between various phospholipase actions on human red cell membranes and the interfacial phospholipid pressure in monolayers. Biochim. Biophys. Acta 406, 97-107.
42. Li, Y., Heitz, F., Le Grimellec, C., and Cole, R. B., (2004) Hydrophobic component in noncovalent binding of fusion peptides to lipids as observed by electrospray mass spectrometry. Rapid Commun. Mass Spectrom. 18, 135-137.
43. Wimley, W. C., and White, S. H., (2000) Designing transmembrane α-helices that insert spontaneously. Biochemistry 39, 4432-4442.
44. White, S. H., and Wimley, W. C., (1999) Membrane protein folding and stability: physical principles. Annu. Rev. Biophys. Biomol. Struct. 28, 319-365.
45. th American Peptide Symposium (in press).