Structural permutation of potent cytotoxin, polytheonamide B: Discovery of cytotoxic peptide with altered activity

ACS Medicinal Chemistry Letters

Volumn 4, Issue 1, 2013, Pages 52-56

  Itoh, Hiroaki ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Cytotoxic agents; natural products; solid phase synthesis; structure activity relationships; synthetic ion channels

Indexed keywords

ANTINEOPLASTIC AGENT; GRAMICIDIN; ION CHANNEL; LIPOSOME; POLYTHEONAMIDE B; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; IC 50; ION EXCHANGE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SOLID; STRUCTURE ACTIVITY RELATION;

EID: 84872304749     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml300264c     Document Type: Article

References (30)

1. Hamada, T.; Matsunaga, S.; Yano, G.; Fusetani, N. Polytheonamides A and B, Highly Cytotoxic, Linear Polypeptides with Unprecedented Structural Features, from the Marine Sponge Theonella swinhoei J. Am. Chem. Soc. 2005, 127, 110-118
2. Hamada, T.; Sugawara, T.; Matsunaga, S.; Fusetani, N. Polytheonamides, Unprecedented Highly Cytotoxic Polypeptides, from the Marine Sponge Theonella swinhoei: 1. Isolation and Component Amino Acids Tetrahedron Lett. 1994, 35, 719-720
3. Hamada, T.; Matsunaga, S.; Fujiwara, M.; Fujita, K.; Hirota, H.; Schmucki, R.; Güntert, P.; Fusetani, N. Solution Structure of Polytheonamide B, a Highly Cytotoxic Nonribosomal Polypeptide from Marine Sponge J. Am. Chem. Soc. 2010, 132, 12941-12945
4. Iwamoto, M.; Shimizu, H.; Muramatsu, I.; Oiki, S. A Cytotoxic Peptide from a Marine Sponge Exhibits Ion Channel Activity through Vectorial-Insertion into the Membrane FEBS Lett. 2010, 584, 3995-3999
5. Oiki, S.; Muramatsu, I.; Matsunaga, S.; Fusetani, N. A Channel-Forming Peptide Toxin: Polytheonamide from Marine Sponge (Theonella swinhoei). Folia Pharmacol. Jpn. 1997, 110 (Suppl. 1), 195-198.
6. Hotchkiss, R. D.; Dubos, R. J. Fractionation of the Bactericidal Agent from Cultures of a Soil Bacillus J. Biol. Chem. 1940, 132, 791-792
7. Gramicidin and related ion channel-forming peptides; Chadwick, D. J.; Cardew, G., Eds.; Wiley & Sons: Chichester, 1999.
8. Inoue, M.; Shinohara, N.; Tanabe, S.; Takahashi, T.; Okura, K.; Itoh, H.; Mizoguchi, Y.; Iida, M.; Lee, N.; Matsuoka, S. Total Synthesis of the Large Non-Ribosomal Peptide Polytheonamide B Nat. Chem. 2010, 2, 280-285
9. Inoue, M. Total Synthesis and Functional Analysis of Non-Ribosomal Peptides Chem. Rec. 2011, 11, 284-294
10. Inoue, M.; Matsuoka, S. Convergent Total Synthesis of the Complex Non-Ribosomal Peptide Polytheonamide B Isr. J. Chem. 2011, 51, 346-358
11. Matsuoka, S.; Shinohara, N.; Takahashi, T.; Iida, M.; Inoue, M. Functional Analysis of Synthetic Substructures of Polytheonamide B: A Transmembrane Channel-Forming Peptide Angew. Chem., Int. Ed. 2011, 50, 4879-4883
12. Shinohara, N.; Itoh, H.; Matsuoka, S.; Inoue, M. Selective Modification of the N-Terminal Structure of Polytheonamide B Significantly Changes its Cytotoxicity and Activity as an Ion Channel ChemMedChem 2012, 7, 1770-1773
13. Itoh, H.; Matsuoka, S.; Kreir, M.; Inoue, M. Design, Synthesis and Functional Analysis of Dansylated Polytheonamide Mimic: An Artificial Peptide Ion Channel J. Am. Chem. Soc. 2012, 134, 14011-14018
14. Bollhagen, R.; Schmiedberger, M.; Barlos, K.; Grell, E. A New Reagent for the Cleavage of Fully Protected Peptides Synthesised on 2-Chlorotrityl Chloride Resin J. Chem. Soc., Chem. Commun. 1994, 2559-2560
15. Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. 2-Chlorotrityl Chloride Resin. Studies on Anchoring of Fmoc-Amino Acids and Peptide Cleavage Int. J. Peptide Protein Res. 1991, 37, 513-520
16. Fmoc Solid Phase Peptide Synthesis; Chan, W. C.; White, P. D., Eds.; Oxford University Press: New York, 2000.
17. Carpino, L. A. 1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive J. Am. Chem. Soc. 1993, 115, 4397-4398
18. Inverarity, I. A.; Hulme, A. N. Marked Small Molecule Libraries: A Truncated Approach to Molecular Probe Design Org. Biomol. Chem. 2007, 5, 636-643
19. Tornøe, C. W.; Christensen, C.; Meldal, M. 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. 2002, 67, 3057-3064
20. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Click Chemistry Reactions in Medicinal Chemistry: Applications of the 1,3-dipolar Cycloaddition Between Azides and Alkynes Med. Res. Rev. 2008, 28, 278-308
21. Kolb, H. C.; Sharpless, K. B. The Growing Impact of Click Chemistry on Drug Discovery Drug Discovery Today 2003, 8, 1128-1137
22. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021
23. Weygand, F.; Steglich, W.; Bjarnason, J. Leicht abspaltbare Schutzgruppen für die Säureamidfunktion, 3. Derivate des Asparagins und Glutamins mit 2.4-dimethoxy-benzyl-und 2.4.6-trimethoxy-benzyl-geschützten Amidgruppen Chem. Ber. 1968, 101, 3642-3648
24. Pearson, D. A.; Blanchette, M.; Baker, M. L.; Guindon, C. A. Trialkylsilanes as Scavengers for the Trifluoroacetic Acid Deblocking of Protecting Groups in Peptide Synthesis Tetrahedron Lett. 1989, 30, 2739-2742
25. Scudiero, D. A.; Shoemaker, R. H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofziger, T. H.; Currens, M. J.; Seniff, D.; Boyd, M. R. Evaluation of a Soluble Tetrazolium/Formazan Assay for Cell Growth and Drug Sensitivity in Culture Using Human and Other Tumor Cell Lines Cancer Res. 1988, 48, 4827-4833
26. Roehm, N. W.; Rodgers, G. H.; Hatfield, S. M.; Glasebrook, A. L. An Improved Colorimetric Assay for Cell Proliferation and Viability Utilizing the Tetrazolium Salt XTT J. Immunol. Methods 1991, 142, 257-265
27. Otis, F.; Racine-Berthiaume, C.; Voyer, N. How Far Can a Sodium Ion Travel within a Lipid Bilayer? J. Am. Chem. Soc. 2011, 133, 6481-6483
28. Clement, N. R.; Gould, J. M. Pyranine (8-Hydroxy-1,3,6- pyrenetrisulfonate) as a Probe of Internal Aqueous Hydrogen Ion Concentration in Phospholipid Vesicles Biochemistry 1981, 20, 1534-1538
29. 2+ in Lymphocytes J. Cell Biol. 1982, 95, 189-196
30. The fluorescence intensity was converted to the intracellular pH values according to the calibration curve obtained by using ion transporter nigericin. See: Thomas, J. A.; Buchsbaum, R. N.; Zimniak, A.; Racker, E. Intracellular pH Measurements in Ehrlich Ascites Tumor Cells Utilizing Spectroscopic Probes Generated in Situ Biochemistry 1979, 18, 2210-2218