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Arginine-Rich Molecular Transporters for Drugs 159 biological activity, as is the case for amphipathic, antimicrobial peptides. 19,20 Increased flexibility in the backbone or the side chains could allow the guanidine headgroups to interact more effectively with negative charges on the cell surface. Using CPK models, increasing the number of methylenes between the arginines not only allows them to interact with negative charges further apart than homopolymers of arginine but, interestingly, also permits the guanidines to pack more closely and interact with putative negative charges that are closely spaced. Further experiments are needed to distinguish among these possible explanations. REFERENCES 1. Mitchell, D.J. et al., Polyarginine enters cells more efficiently than other polycationic homopolymers, J. Pept. Res., 56, 318, 2000. 2. Wender, P.A. et al., The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters, Proc. Natl. Acad. Sci. U.S.A., 97, 13003, 2000. 3. Zuckermann, R. et al., Efficient method for the preparation of peptoids [oligo (Nsubstituted glycines)] by sub-nanomer solid phase synthesis, JACS, 114, 10646, 1992. 4. Pons, J. et al., A constrained diketopiperazine as a new scaffold for the synthesis of peptidomimetics, Eur. J. Org. Chem., 1998, 853, 1998. 5. Murphy, J.E. et al., A combinatorial approach to the discovery of efficient cationic peptoid reagents for gene delivery, Proc. Natl. Acad. Sci. U.S.A., 95, 1517, 1998. 6. Simon, R.J. et al., Peptoids: a modular approach to drug discovery, Proc. Natl. Acad. Sci. U.S.A., 89, 9367, 1992. 7. Kale L. et al., NAMD2: greater scalability for parallel molecular dynamics, J. Computational Physi., 151, 283, 1999. 8. MacKerell, B.D. et al., All atom empirical potential for molecular modeling and dynamics studies of proteins, J. Phys. Chem., 102, 3586, 1998. 9. Humphrey, W., Dalke, A., and Schulten, K., VMD — visual molecular dynamics, J. Mol. Graphics, 14, 33, 1996. 10. Miller, S. et al., Proteolystic studies of homologous peptide and N-substituted glycine peptoid oligomers, Bioorg. Phys. Lett., 4, 2657, 1994. 11. Tamilarasu, N., Huq, I., and Rana, T., High affinity and specific binding of HIV-1 TAR RNA by a Tat-derived oligourea, JACS, 121, 1597, 1999. 12. Hamy, F. et al., An inhibitor of the Tat/TAR RNA interaction that effectively sup<strong>press</strong>es HIV-1 replication, Proc. Natl. Acad. Sci. U.S.A., 94, 3548, 1997. 13. Bernatowicz, M., 1H-pyrrole-1-carboxamidine hydrochloride: an attractive reagent for guanylation of amines and its application to peptide synthesis, J. Org. Chem. 57, 2497, 1992. 14. Kruijtzer, J. et al., Solid-phase syntheses of peptoids using Fmoc-protected N-substituted glycines: the synthesis of (retro) peptoids of Leu-enkephalin and substance P, Chem. A Eur. J., 4, 1570, 1998. 15. Heizmann, G. and Felder, E.R., Synthesis of an N-3-guanidinopropylglycine (Narg) derivative as a versatile building block for solid-phase peptide and peptoid synthesis, Pept. Res., 7, 328, 1994. 16. Feichtinger, K. et al., Triurethane-protected guanidines and triflyldiurethane-protected guanidines: new reagents for guanidinylation reactions, J. Org. Chem., 63, 8432, 1998.
160 Cell-Penetrating Peptides: Processes and Applications 17. Bellet–Amalric, E. et al., Interaction of the third helix of antennapedia homeodomain and a phospholipid monolayer, studied by ellipsometry and PM-IR RAS at the air–water interface, Biochim. Biophys. Acta, 1467, 131, 2000. 18. Magzoub, M. et al., Interaction and structure induction of cell-penetrating peptides in the presence of phospholipid vesicles, Biochim. Biophys. Acta, 1512, 77, 2001. 19. Dathe, M. and Wieprecht, T., Structural features of helical antimicrobial peptides: their potential to modulate activity on model membranes and biological cells, Biochim. Biophys. Acta, 1462, 71, 1999. 20. Shai, Y., Mechanism of the binding, insertion and destabilization of phospholipid bilayer membranes by alpha-helical antimicrobial and cell non-selective membranelytic peptides, Biochim. Biophys. Acta, 1462, 55, 1999.
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CELL- PENETRATING PEPTIDES Processe
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Pharmacology and Toxicology: Basic
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Library of Congress Cataloging-in-P
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to the handbook are prominent resea
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REFERENCES 1. Green, M. and Loewens
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Contributors Mats Andersson Microbi
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Erin T. Pelkey Department of Chemis
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Contents Section I Classes of Cell-
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Chapter 16 Cell-Penetrating Peptide
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The Tat-Derived Cell-Penetrating Pe
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24 Cell-Penetrating Peptides: Proce
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3 Transportans Margus Pooga, Mattia
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Transportans 55 Indeed, galparan is
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Transportans 57 especially the endo
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Transportans 59 In the penetration
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Transportans 61 A 21-mer antisense
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Transportans 63 Commonly, the prote
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Transportans 65 antibiotin antibodi
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Transportans 67 For cross-linking o
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Transportans 69 and still retain ef
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Model Amphipathic Peptides 73 its D
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Model Amphipathic Peptides 75 pmol/
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TABLE 4.1 Internalization of Peptid
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TABLE 4.2 Internalization of Peptid
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Model Amphipathic Peptides 81 relat
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Model Amphipathic Peptides 87 A cat
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Model Amphipathic Peptides 89 At th
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Model Amphipathic Peptides 91 16. H
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Signal Sequence-Based Cell-Penetrat
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FIGURE 9.8 The center of the figure
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Structure Prediction of CPPs and It
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Biophysical Studies of Cell-Penetra
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Toxicity and Side Effects of Cell-P
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264 Cell-Penetrating Peptides: Proc
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Kinetics of Uptake of Cell-Penetrat
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Cell-Penetrating Peptide Conjugatio
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FIGURE 15.9 (Color Figure 15.9 foll
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Cell-Penetrating Peptides as Vector
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TABLE 16.1 Examples of Transport of
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CPP 2 Cargo or mRNA CAP Antisense A
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Microbial Membrane-Permeating Pepti
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Index A Abaecin, 129 Abz radiolabel
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Index 399 Diffraction, 168 Disulphi
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Index 401 structure prediction, 187
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Index 403 pRB proteins, Tat-E1A bin
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Index 405 lipid perturbation (secon
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