Antimicrobial cyclic decapeptides with anticancer activity

Peptides

Volumn 31, Issue 11, 2010, Pages 2017-2026

  Feliu, Lidia ^a   Oliveras, Glria ^a,b   Cirac, Anna D ^a   Besalú, Emili ^a   Rosés, Cristina ^a   Colomer, Ramon ^c   Bardají, Eduard ^a   Planas, Marta ^a   Puig, Teresa ^a,b  

^a UNIVERSITY OF GIRONA   (Spain)

^b CATALAN INSTITUTE OF ONCOLOGY   (Spain)

^c MD ANDERSON CANCER CENTER   (Spain)

Author keywords

Apoptosis; Cervical carcinoma; Cyclopeptides; Design of experiments; Pharmacological synergism

Indexed keywords

ANTINEOPLASTIC AGENT; CISPLATIN; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PEPTID BPC 184; PEPTID BPC 194; PEPTID BPC 198; PEPTID BPC 202; PEPTID BPC 58; PEPTID BPC 60; PEPTID BPC 62; PEPTID BPC 64; PEPTID BPC 66; PEPTID BPC 68; PEPTID BPC 70; PEPTID BPC 72; PEPTID BPC 74; PEPTID BPC 76; PEPTID BPC 78; PEPTID BPC 80; PEPTID BPC 82; PEPTIDE BPC 88; PEPTIDE BPC 94; PEPTIDE BPC 96; PEPTIDE BPC 98; PEPTIDE DERIVATIVE; POLYPEPTIDE ANTIBIOTIC AGENT; PROTEIN P53; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMINO ACID SEQUENCE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CARCINOMA CELL; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG SYNTHESIS; FIBROBLAST; HELA CELL; HUMAN; HUMAN CELL; IC 50; IMMUNOBLOTTING; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; SERUM; UTERINE CERVIX CARCINOMA;

ANTIMICROBIAL CATIONIC PEPTIDES; ANTINEOPLASTIC AGENTS; APOPTOSIS; BREAST NEOPLASMS; CELL LINE, TUMOR; CISPLATIN; DRUG SYNERGISM; HELA CELLS; HUMANS; MITOGEN-ACTIVATED PROTEIN KINASE 1; MITOGEN-ACTIVATED PROTEIN KINASE 3; OLIGOPEPTIDES; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; POLY(ADP-RIBOSE) POLYMERASES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 77957849446     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2010.07.027     Document Type: Article

References (47)

1. J.M. Barroso, and E. Besalú Design of experiments applied to QSAR: ranking a set of compounds and establishing a statistical significance test J Mol Struct (Theochem) 727 2005 89 96
2. G. Bar-Sela, R. Epelbaum, and M. Schaffer Curcumin as an anti-cancer agent: review of the gap between basic and clinical applications Curr Med Chem 2009 [Epub ahead of print]
3. B. Bechinger Structure and function of membrane-lytic peptides Crit Rev Plant Sci 23 2004 271 292
4. G.E.P. Box, W.G. Hunter, and J.S. Hunter Statistics for experimenters. An introduction to design, data analysis, and model building 1978 John Wiley & Sons, Inc. New York
5. K.A. Brogden Antimicrobial peptides: pore formers or metabolic inhibitors in bacteria? Nat Rev Microbiol 3 2005 238 250
6. S.H. Chung, and P.F. Lambert Prevention and treatment of cervical cancer in mice using estrogen receptor antagonists Proc Natl Acad Sci USA 106 2009 19467 19472
7. S.M. Cowell, Y.S. Lee, J.P. Cain, and V.J. Hruby Exploring Ramachandran and Chi space: conformationally constrained amino acids and peptides in the design of bioactive polypeptide ligands Curr Med Chem 11 2004 2785 2798
8. L.J. Cruz, J.R. Luque-Ortega, L. Ribas, F. Albericio, and F. Kahalalide An antitumor depsipeptide in clinical trials, and its analogues as effective antileishmanial agents Mol Pharmaceut 6 2009 813 824
9. M. Dathe, H. Nikolenko, G. Klose, and M. Bienert Cyclization increases the antimicrobial activity and selectivity of arginine- and tryptophan- containing hexapeptides Biochemistry 43 2004 9140 9150
10. 12 Org Biomol Chem 6 2008 4134 4141
11. G. Faircloth, C. Cuevas, and F. Kahalalide ES285: potent anticancer agents from marine moluscs Prog Mol Subcell Biol 43 2006 363 379
12. V. Frecer, B. Ho, and J.L. Ding De novo design of potent antimicrobial peptides Antimicrob Agents Chemother 48 2004 3349 3357
13. 2 symmetric cyclopeptide family J Med Chem 51 2008 3194 3202
14. R.E.W. Hancock, and H.G. Sahl Antimicrobial and host defense peptides as new anti-infective therapeutic strategies Nature Biotechnol 24 2006 1551 1557
15. D.W. Hoskin, and A. Ramamoorthy Studies on anticancer activities of antimicrobial peptides Biochim Biophys Acta 1778 2008 357 375
16. L. Hui, K. Leung, and H.M. Chen The combined effects of antibacterial peptide cecropin A and anticancer agents on leukemia cells Anticancer Res 22 2002 2811 2816
17. H. Jenssen, P. Hamill, and R.E.W. Hancock Peptide antimicrobial agents Clin Microbiol Rev 19 2006 491 511
18. S. Jiang, C. Liao, L. Bindu, B. Yin, K.W. Worthy, and R.J. Fisher Discovery of thioether-bridged cyclic pentapeptides binding to Grb2-SH2 domain with high affinity Bioorg Med Chem Lett 19 2009 2693 2698
19. C.L. Johnson, D. Lu, J. Huang, and A. Basu Regulation of p53 stabilization by DNA damage and protein kinase Mol Cancer Ther 1 2002 861 867
20. S.A. Kates, N.A. Solé, C.R. Johnson, D. Hudson, G. Barany, and F. Albericio A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides Tetrahedron Lett 34 1993 1549 1552
21. M. Katsara, T. Tselios, S. Deraos, G. Deraos, M. Minos-Timotheos, and E. Lazoura Round and round we go: cyclic peptides in disease Curr Med Chem 13 2006 2221 2232
22. S. Kim, S.S. Kim, Y.-J. Bang, S.-J. Kim, and B.J. Lee In vitro activities of native and design peptide antibiotics against drug sensitive and resistant tumor cell lines Peptides 24 2003 945 953
23. C. Leuschner, and W. Hansel Membrane disrupting lytic peptides for cancer treatments Curr Pham Design 10 2004 2299 2310
24. T. Liu, S.H. Joo, J.L. Voorhees, C.L. Brooks, and D. Pei Synthesis and screening of a cyclic peptide library: discovery of small-molecule ligands against human prolactin receptor Bioorg Med Chem 17 2009 1026 1033
25. J.S. Mader, and D.W. Hoskin Cationic antimicrobial peptides as novel cytotoxic agents for cancer treatment Expert Opin Investig Drugs 15 2006 933 946
26. J.A. Menendez, R. Lupu, and R. Colomer Inhibition of tumor-associated fatty acid synthase hyperactivity induces synergistic chemosensitization of HER-2/neu-overexpressing human breast cancer cells to docetaxel (taxotere) Breast Cancer Res Treat 84 2004 183 195
27. S. Mocellin, P. Pilati, and D. Nitti Peptide-based anticancer vaccines: recent advances and future perspectives Curr Med Chem 16 2009 4779 4796
28. S. Monroc, E. Badosa, E. Besalú, M. Planas, E. Bardají, and E. Montesinos Improvement of cyclic decapeptides against plant pathogenic bacteria using a combinatorial chemistry approach Peptides 27 2006 2575 2584
29. H. Morita, and K. Takeya Bioactive cyclic peptides from higher plants Heterocycles 80 2010 739 764
30. Y. Ohsaki, A.F. Gazdar, H.-C. Chen, and B.E. Johnson Antitumor activity of magainin analogues against human lung cancer cell lines Cancer Res 52 1992 3534 3538
31. N. Papo, and Y. Shai Host defense peptides as new weapons in cancer treatment Cell Mol Life Sci 62 2005 784 790
32. S.A. Park, H.J. Park, B.I. Lee, Y.H. Ahn, S.U. Kim, and K.S. Choi Bcl-2 blocks cisplatin-induced apoptosis by suppression of ERK-mediated p53 accumulation in B104 cells Mol Brain Res 93 2001 18 26
33. A. Peschel, and H.G. Sahl The co-evolution of host cationic antimicrobial peptides and microbial resistance Nat Rev Microbiol 4 2006 529 536
34. C.H. Qin, X. Bu, X. Zhong, N.L.J. Ng, and Z. Guo Optimization of antibacterial cyclic decapeptides J Comb Chem 6 2004 398 406
35. S. Ropero, J.A. Menéndez, A. Vázquez-Martín, S. Montero, H. Cortés-Funes, and R. Colomer Trastuzumab plus tamoxifen: anti-proliferative and molecular interactions in breast carcinoma Breast Cancer Res Treat 86 2004 125 137
36. H. Schröder-Borm, R. Bakalova, and J. Andrä The NK-lysin derived peptide NK-2 preferentially kills cancer cells with increased surface levels of negatively charged phosphatidylserine FEBS Lett 579 2005 6128 6134
37. Y. Shai Mode of action of membrane active antimicrobial peptides Biopolymers 66 2002 236 248
38. T. Takahashi, H. Nagamiya, T. Doi, P.G. Griffiths, and A.M. Bray Solid phase library synthesis of cyclic depsipeptides: aurilide and aurilide analogues J Comb Chem 5 2003 414 428
39. S. Ueda, S. Oishi, Z. Wang, T. Araki, H. Tamamura, and J. Cluzeau Structure-activity relationships of cyclic peptide-based chemokine receptor CXCR4 antagonists: disclosing the importance of side-chain and backbone functionalties J Med Chem 50 2007 192 198
40. P. Vlieghe, V. Lisowski, J. Martinez, and M. Khrestchatisky Synthetic therapeutic peptides: science and market Drug Discov Today 15 2010 40 56
41. W. Woessmann, X. Chen, and A. Borkhardt Ras-mediated activation of ERK by cisplatin induces cell death independently of p53 in osteosarcoma and neuroblastoma cell lines Cancer Chemother Pharmacol 50 2002 397 404
42. H.-S. Won, M.-D. Seo, S.-J. Jung, S.-J. Lee, S.-J. Kang, and W.-S. Son Structural determinants for the membrane interaction of novel bioactive undecapeptides derived from gaegurin 5 J Med Chem 49 2006 4886 4895
43. N. Yao, W. Xiao, X. Wang, J. Marik, S.H. Park, and Y. Takada Discovery of targeting ligands for breast cancer cells using the one-bead one-compound combinatorial method J Med Chem 52 2009 126 133
44. X. Yao, K. Panichpisal, N. Kurtzman, and K. Nugent Cisplatin nephrotoxicity: a review Am J Med Sci 334 2007 115 124
45. M.R. Yeaman, and N.Y. Yount Mechanisms of antimicrobial peptide action and resistance Pharmacol Rev 55 2003 27 55
46. L. Zhang, and T.J. Falla Antimicrobial peptides: therapeutic potential Expert Opin Pharmacother 7 2006 653 663
47. Y. Zhang, S. Zhou, A.-S. Wavreille, J. DeWille, and D. Pei Cyclic peptidyl inhibitors of Grb2 and tensin SH2 domains identified from combinatorial libraries J Comb Chem 10 2008 247 255