Cell penetrating peptoids (CPPos): Synthesis of a small combinatorial library by using IRORI MiniKans

Pharmaceuticals

Volumn 5, Issue 12, 2012, Pages 1265-1281

  Kölmel, Dominik K ^a   Fürniss, Daniel ^a   Susanto, Steven ^b   Lauer, Andrea ^b   Grabher, Clemens ^b   Bräse, Stefan ^a,b   Schepers, Ute ^b  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Cell penetrating; Combinatorial chemistry; IRORI; Library; Peptoid; Split and mix; Sub monomer

Indexed keywords

CELL PENETRATING PEPTIDE; RHODAMINE B;

ARTICLE; CELL ORGANELLE; CELL TRANSPORT; CELLULAR DISTRIBUTION; COMBINATORIAL LIBRARY; CONFOCAL MICROSCOPY; ENDOCYTOSIS; ENDOSOME; FEMALE; FLUORESCENCE MICROSCOPY; HELA CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; LIPOPHILICITY; PEPTIDE LIBRARY; PHENOTYPE; PROTEIN STRUCTURE; SOLID PHASE SYNTHESIS;

EID: 84870277955     PISSN: None     EISSN: 14248247     Source Type: Journal    
DOI: 10.3390/ph5121265     Document Type: Article

References (61)

1. Wadia, J.S.; Dowdy, S.F. Protein transduction technology. Curr. Opin. Biotechnol. 2002, 13, 52-56.
2. Vives, E.; Richard, J.P.; Rispal, C.; Lebleu, B. TAT peptide internalization: Seeking the mechanism of entry. Curr. Protein. Pept. Sci. 2003, 4, 125-132.
3. Simon, R.J.; Kania, R.S.; Zuckermann, R.N.; Huebner, V.D.; Jewell, D.A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; et al. Peptoids: A modular approach to drug discovery. Proc. Natl. Acad. Sci. USA 1992, 89, 9367-9371.
4. Peretto, I.; Sanchez-Martin, R.M.; Wang, X.H.; Ellard, J.; Mittoo, S.; Bradley, M. Cell penetrable peptoid carrier vehicles: Synthesis and evaluation. Chem. Commun. 2003, 2312-2313.
5. Sawant, R.; Torchilin, V. Intracellular transduction using cell-penetrating peptides. Mol. Biosyst. 2010, 6, 628-640
6. Ezzat, K.; Zaghloul, E.M.; El Andaloussi, S.; Lehto, T.; El-Sayed, R.; Magdy, T.; Smith, C.I.; Langel, U. Solid formulation of cell-penetrating peptide nanocomplexes with siRNA and their stability in simulated gastric conditions. J. Control. Release 2012, 162, 1-8.
7. Holm, T.; Raagel, H.; Andaloussi, S.E.; Hein, M.; Mae, M.; Pooga, M.; Langel, U. Retroinversion of certain cell-penetrating peptides causes severe cellular toxicity. Biochim. Biophys. Acta 2011, 1808, 1544-1551.
8. Yin, H.; Moulton, H.M.; Betts, C.; Seow, Y.; Boutilier, J.; Iverson, P.L.; Wood, M.J. A fusion peptide directs enhanced systemic dystrophin exon skipping and functional restoration in dystrophin-deficient mdx mice. Hum. Mol. Genet. 2009, 18, 4405-4414.
9. Umezawa, N.; Gelman, M.A.; Haigis, M.C.; Raines, R.T.; Gellman, S.H. Translocation of a betapeptide across cell membranes. J. Am. Chem. Soc. 2002, 124, 368-369.
10. Nakase, I.; Takeuchi, T.; Tanaka, G.; Futaki, S. Methodological and cellular aspects that govern the internalization mechanisms of arginine-rich cell-penetrating peptides. Adv. Drug Deliv. Rev. 2008, 60, 598-607.
11. Gademann, K.; Hintermann, T.; Schreiber, J.V. Beta-peptides: Twisting and turning. Curr. Med. Chem. 1999, 6, 905-925.
12. Murphy, J.E.; Uno, T.; Hamer, J.D.; Cohen, F.E.; Dwarki, V.; Zuckermann, R.N. A combinatorial approach to the discovery of efficient cationic peptoid reagents for gene delivery. Proc. Natl. Acad. Sci. USA 1998, 95, 1517-1522.
13. Uno, T.; Beausoleil, E.; Goldsmith, R.A.; Levine, B.H.; Zuckermann, R.N. New submonomers for poly N-substituted glycines (peptoids). Tetrahedron Lett. 1999, 40, 1475-1478.
14. Wender, P.A.; Mitchell, D.J.; Pattabiraman, K.; Pelkey, E.T.; Steinman, L.; Rothbard, J.B. The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters. Proc. Natl. Acad. Sci. USA 2000, 97, 13003-13008.
15. Wright, L.R.; Rothbard, J.B.; Wender, P.A. Guanidinium rich peptide transporters and drug delivery. Curr. Prot. Pept. Sci. 2003, 4, 105-124.
16. Schröder, T.; Schmitz, K.; Niemeier, N.; Balaban, T.S.; Krug, H.F.; Schepers, U.; Bräse, S. Solidphase synthesis, bioconjugation, and toxicology of novel cationic oligopeptoids for cellular drug delivery. Bioconjug. Chem. 2007, 18, 342-354.
17. Schröder, T.; Niemeier, N.; Afonin, S.; Ulrich, A.S.; Krug, H.F.; Bräse, S. Peptoidic amino- and guanidinium-carrier systems: targeted drug delivery into the cell cytosol or the nucleus. J. Med. Chem. 2008, 51, 376-379.
18. Eggenberger, K.; Birtalan, E.; Schröder, T.; Bräse, S.; Nick, P. Passage of Trojan peptoids into plant cells. ChemBioChem 2009, 10, 2504-2512.
19. Rudat, B.; Birtalan, E.; Thomé, I.; Kölmel, D.K.; Horhoiu, V.L.; Wissert, M.D.; Lemmer, U.; Eisler, H.J.; Balaban, T.S.; Bräse, S. Novel pyridinium dyes that enable investigations of peptoids at the single-molecule level. J. Phys. Chem. B 2010, 114, 13473-13480
20. Birtalan, E.; Rudat, B.; Kölmel, D.K.; Fritz, D.; Vollrath, S.B.L.; Schepers, U.; Bräse, S. Investigating rhodamine B-Labeled peptoids: Scopes and limitations of its applications. Biopolymers 2011, 96, 694-701.
21. Lee, M.M.; French, J.M.; Disney, M.D. Influencing uptake and localization of aminoglycosidefunctionalized peptoids. Mol. Biosyst. 2011, 7, 2441-2451.
22. Seo, J.; Ren, G.; Liu, H.; Miao, Z.; Park, M.; Wang, Y.; Miller, T. M.; Barron, A. E.; Cheng, Z. In Vivo biodistribution and small animal PET of (64)Cu-Labeled antimicrobial peptoids. Bioconjug. Chem. 2012, 23 1069-1079.
23. Huang, W.; Seo, J.; Lin, J.S.; Barron, A.E. Peptoid transporters: Effects of cationic, amphipathic structure on their cellular uptake. Mol. Biosyst. 2012, 8, 2626-2628.
24. Tan, N. C.; Yu, P.; Kwon, Y.U.; Kodadek, T. High-throughput evaluation of relative cell permeability between peptoids and peptides. Bioorg. Med. Chem. 2008, 16, 5853-5861.
25. Aditya, A.; Kodadek, T., Incorporation of heterocycles into the backbone of peptoids to generate diverse peptoid-inspired one bead one compound libraries. ACS Comb. Sci. 2012, 14, 164-169.
26. Diaz-Mochon, J.J.; Fara, M.A.; Sanchez-Martin, R.M.; Bradley, M. Peptoid dendrimersmicrowave- assisted solid-phase synthesis and transfection agent evaluation. Tetrahedron Lett. 2008, 49, 923-926.
27. Fara, M.A.; Diaz-Mochon, J.J.; Bradley, M. Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labelled peptides-a gentle heat goes a long way. Tetrahedron Lett. 2006, 47, 1011-1014.
28. Li, S.; Bowerman, D.; Marthandan, N.; Klyza, S.; Luebke, K.J.; Garner, H.R.; Kodadek, T. Photolithographic synthesis of peptoids. J. Am. Chem. Soc. 2004, 126, 4088-4089.
29. Olivos, H.J.; Alluri, P.G.; Reddy, M.M.; Salony, D.; Kodadek, T. Microwave-assisted solid-phase synthesis of peptoids. Org. Lett. 2002, 4, 4057-4059.
30. Goodman, B. Managing the workflow of a high-throughput organic synthesis laboratory: A marriage of automation and information management technologies. J. Lab. Automation 1999, 4, 48-52.
31. Cheung, A. W.; Qi, L.; Gore, V.; Chu, X.J.; Bartkovitz, D.; Kurylko, G.; Swistok, J.; Danho, W.; Chen, L.; Yagaloff, K. Preparation of human Melanocortin-4 receptor agonist libraries: Linear peptides X-Y-DPhe7-Arg8-Trp(or 2-Nal)9-Z-NH2. Bioorg. Med. Chem. Lett. 2005, 15, 5504-5508.
32. Xiao, X.Y.; Li, R.S.; Zhuang, H.; Ewing, B.; Karunaratne, K.; Lillig, J.; Brown, R.; Nicolaou, K.C. Solid-phase combinatorial synthesis using MicroKan reactors, Rf tagging, and directed sorting. Biotechnol. Bioeng. 2000, 71, 44-50
33. Nicolaou, K.C.; Xiao, X.Y.; Parandoosh, Z.; Senyei, A.; Nova, M.P. Radiofrequency encoded combinatorial chemistry. Angew. Chem. Int. Ed. 1995, 34, 2289-2291.
34. Nagai, K.; Doi, T.; Sekiguchi, T.; Namatame, I.; Sunazuka, T.; Tomoda, H.; Omura, S.; Takahashi, T. Synthesis and biological evaluation of a beauveriolide analogue library. J. Comb. Chem. 2006, 8, 103-109.
35. Nicolaou, K.C.; Vourloumis, D.; Li, T.H.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; et al. Designed epothilones: Combinatorial synthesis, tubulin assembly properties, and cytotoxic action against taxol-resistant tumor cells. Angew. Chem. Int. Ed. 1997, 36, 2097-2103.
36. Marsault, E.; Hoveyda, H.R.; Peterson, M.L.; Gagnon, R.; Vezina, M.; Pinault, J.F.; Landry, A.; Saint-Louis, C.; Ouellet, L.G.; Beauchemin, S.; et al. High throughput solid phase parallel synthesis of macrocyclic peptidomimetics. Adv. Exp. Med. Biol. 2009, 611, 15-16.
37. Zuckermann, R.N.; Kerr, J.M.; Kent, S.B.H.; Moos, W.H. Efficient method for the preparation of peptoids [Oligo(N-Substituted Glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc. 1992, 114, 10646-10647.
38. Culf, A.S.; Ouellette, R.J. Solid-phase synthesis of N-substituted glycine oligomers (alphapeptoids) and derivatives. Molecules 2010, 15, 5282-5335.
39. Goun, E.A.; Shinde, R.; Dehnert, K.W.; Adams-Bond, A.; Wender, P.A.; Contag, C.H.; Franc, B.L. Intracellular cargo delivery by an octaarginine transporter adapted to target prostate cancer cells through cell surface protease activation. Bioconjug. Chem. 2006, 17, 787-796.
40. Wender, P.A.; Jessop, T.C.; Pattabiraman, K.; Pelkey, E.T.; VanDeusen, C.L. An efficient, scalable synthesis of the molecular transporter octaarginine via a segment doubling strategy. Org. Lett. 2001, 3, 3229-3232.
41. Schröder, T.; Quintilla, A.; Setzler, J.; Birtalan, E.; Wenzel, W.; Bräse, S. Joint experimental and theoretical investigation of the propensity of peptoids as drug carriers. WSEAS Trans. Biol. Biomed. 2007, 4, 145-148.
42. Chen, C.L.; Qi, J.; Zuckermann, R.N.; DeYoreo, J.J. Engineered biomimetic polymers as tunable agents for controlling CaCO3 mineralization. J. Am. Chem. Soc. 2011, 133, 5214-5217.
43. Thakkar, A.; Cohen, A.S.; Connolly, M.D.; Zuckermann, R.N.; Pei, D. High-throughput sequencing of peptoids and peptide-peptoid hybrids by partial edman degradation and mass spectrometry. J. Comb. Chem. 2009, 11, 294-302.
44. Simpson, L. S.; Kodadek, T. A cleavable scaffold strategy for the synthesis of one-bead onecompound cyclic peptoid libraries that can be sequenced by tandem mass spectrometry. Tetrahedron Lett. 2012, 53, 2341-2344.
45. Aquino, C.; Sarkar, M.; Chalmers, M.J.; Mendes, K.; Kodadek, T.; Micalizio, G.C. A biomimetic polyketide-inspired approach to small-molecule ligand discovery. Nat. Chem. 2012, 4, 99-104.
46. Hooks, J.C.; Matharage, J.P.; Udugamasooriya, D.G. Development of homomultimers and heteromultimers of lung cancer-specific peptoids. Biopolymers 2011, 96, 567-577.
47. Klimkait, T.; Felder, E.R.; Albrecht, G.; Hamy, F. Rational optimization of a HIV-1 Tat inhibitor: rapid progress on combinatorial lead structures. Biotechnol. Bioeng. 1998, 61, 155-168.
48. D'Souza, G.G.; Cheng, S.M.; Boddapati, S.V.; Horobin, R.W.; Weissig, V. Nanocarrier-assisted sub-cellular targeting to the site of mitochondria improves the pro-apoptotic activity of paclitaxel. J. Drug Target. 2008, 16, 578-585.
49. Boddapati, S.V.; D'Souza, G.G.; Erdogan, S.; Torchilin, V.P.; Weissig, V. Organelle-targeted nanocarriers: Specific delivery of liposomal ceramide to mitochondria enhances its cytotoxicity in vitro and in vivo. Nano Lett. 2008, 8, 2559-2563.
50. Weissig, V. Targeted drug delivery to mammalian mitochondria in living cells. Expert Opin. Drug. Deliv. 2005, 2, 89-102.
51. Wallace, D.C. Mitochondrial diseases in man and mouse. Science 1999, 283, 1482-1488.
52. Chinnery, P.F.; Turnbull, D.M. Mitochondrial DNA mutations in the pathogenesis of human disease. Mol. Med. Today 2000, 6, 425-432.
53. Wallace, D.C. Mitochondria and cancer: Warburg addressed. Cold Spring Harb. Symp. Quant. Biol. 2005, 70, 363-374.
54. Wallace, D.C. A mitochondrial paradigm of metabolic and degenerative diseases, aging, and cancer: A dawn for evolutionary medicine. Annu. Rev. Genet. 2005, 39, 359-407.
55. Horton, K.L.; Kelley, S.O. Engineered apoptosis-inducing peptides with enhanced mitochondrial localization and potency. J. Med. Chem. 2009, 52, 3293-3299.
56. Horton, K.L.; Stewart, K.M.; Fonseca, S.B.; Guo, Q.; Kelley, S.O. Mitochondria-penetrating peptides. Chem. Biol. 2008, 15, 375-382.
57. Horton, K.L.; Pereira, M.P.; Stewart, K.M.; Fonseca, S.B.; Kelley, S.O. Tuning the activity of mitochondria-penetrating peptides for delivery or disruption. ChemBioChem 2012, 13, 476-485.
58. Kelley, S. O.; Stewart, K. M.; Mourtada, R. Development of novel peptides for mitochondrial drug delivery: Amino acids featuring delocalized lipophilic cations. Pharm. Res. 2011, 28, 2808-2819.
59. Yousif, L.F.; Stewart, K.M.; Horton, K.L.; Kelley, S.O. Mitochondria-penetrating peptides: sequence effects and model cargo transport. ChemBioChem 2009, 10, 2081-2088.
60. Yousif, L.F.; Stewart, K.M.; Kelley, S.O. Targeting mitochondria with organelle-specific compounds: Strategies and applications. ChemBioChem 2009, 10, 1939-1950
61. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. General method for rapid synthesis of multicomponent peptide mixtures. Int. J. Pept. Protein Res. 1991, 37, 487-493.