Selective cancer cell cytotoxicity of enantiomeric 9-mer peptides derived from beetle defensins depends on negatively charged phosphatidylserine on the cell surface

Peptides

Volumn 30, Issue 4, 2009, Pages 660-668

  Iwasaki, Takashi ^a,b   Ishibashi, Jun ^b   Tanaka, Hiromitsu ^b   Sato, Mitsuru ^b   Asaoka, Ai ^b   Taylor, DeMar ^a   Yamakawa, Minoru ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NATIONAL INSTITUTE OF AGROBIOLOGICAL SCIENCES   (Japan)

Author keywords

Enantiomeric peptides; Insect defensin; Myeloma; Negative charge; Phosphatidylserine; Selective cytotoxicity

Indexed keywords

ANTINEOPLASTIC AGENT; DEFENSIN; DEXAMETHASONE; DEXTRO PEPTIDE A; DEXTRO PEPTIDE B; DEXTRO PEPTIDE C; DEXTRO PEPTIDE D; DOXORUBICIN; MELPHALAN; PHOSPHATIDYLSERINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIGENICITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BACTERIAL MEMBRANE; CELL SURFACE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG INHIBITION; DRUG POTENTIATION; DRUG SENSITIVITY; DRUG SYNTHESIS; ENANTIOMER; FLOW CYTOMETRY; HUMAN; HUMAN CELL; MOUSE; MYELOMA; NONHUMAN; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY;

AMINO ACID SEQUENCE; ANIMALS; BEETLES; CELL LINE, TUMOR; DEFENSINS; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; HUMANS; MEMBRANE LIPIDS; MICE; MICROSCOPY, ELECTRON, SCANNING; PEPTIDE FRAGMENTS; PHOSPHATIDYLSERINES; STEREOISOMERISM;

BACTERIA (MICROORGANISMS); COLEOPTERA; HEXAPODA;

EID: 62749091569     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2008.12.019     Document Type: Article

References (44)

1. Baker M.A., Maloy W.L., Zasloff M., and Jacob L.S. Anticancer efficacy of Magainin2 and analogue peptides. Cancer Res 53 (1993) 3052-3057
2. De Beer E.L., Bottone A.E., and Voest E.E. Doxorubicin and mechanical performance of cardiac trabeculae after acute and chronic treatment: a review. Eur J Pharmacol 415 (2001) 1-11
3. Ellerby H.M., Arap W., Ellerby L.M., Kain R., Andrusiak R., and Rio G.D. Anti-cancer activity of targeted pro-apoptotic peptides. Nat Med 5 (1999) 1032-1038
4. Fadok V.A., Bratton D.L., Rose D.M., Pearson A., Ezekewitz R.A., and Henson P.M. A receptor for phosphatidylserine-specific clearance of apoptotic cells. Nature 405 (2000) 85-90
5. Fadok V.A., Voelker D.R., Campbell P.A., Cohen J.J., Bratton D.L., and Henson P.M. Exposure of phosphatidylserine on the surface of apoptotic lymphocytes triggers specific recognition and removal by macrophages. J Immunol 148 (1992) 2207-2216
6. Ferguson L.R., and Pearson A.E. The clinical use of mutagenic anticancer drugs. Mutat Res 355 (1996) 1-12
7. Hancock R.E., and Chapple D.S. Peptide antibiotics. Antimicrob Agents Chemother 43 (1999) 1317-1323
8. Ishibashi J., Saido-Sakanaka H., Yang J., Sagisaka A., and Yamakawa M. Purification, cDNA cloning and modification of a defensin from the coconut rhinoceros beetle, Oryctes rhinoceros. Eur J Biochem 266 (1999) 616-623
9. Iwasaki T., Saido-Sakanaka H., Asaoka A., Taylor D., Ishibashi J., and Yamakawa M. In vitro activity of diastereomeric antimicrobial peptides alone and in combination with antibiotics against methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa. J Insect Biotechnol Sericol 76 (2007) 25-29
10. Koyama Y., Motobu M., Hikosaka K., Yamada M., Nakamura K., Saido-Sakanaka H., et al. Cytotoxicity and antigenicity of antimicrobial synthesized peptides derived from the beetle Allomyrina dichotoma defensin in mice. Int Immunopharmacol 6 (2006) 1748-1753
11. Lehmann J., Retz M., Sidhu S.S., Suttmann H., Sell M., and Paulsen F. Antitumor activity of the antimicrobial peptide magainin II against bladder cancer cell lines. Eur Urol 50 (2006) 141-147
12. Mader J.S., and Hoskin D.W. Cationic antimicrobial peptides as novel cytotoxic agents for cancer treatment. Expert Opin Investig Drugs 15 (2006) 933-946
13. Maeji N.J., Bray A.M., and Geysen H.M. Multi-pin peptide synthesis strategy for T cell determinant analysis. J Immunol Methods 134 (1990) 23-33
14. Merrifield R.B., Juvvadi P., Andreu D., Ubach J., Boman A., and Boman H.G. Retro and retroenantio analogs of cecropin-melittin hybrids. Proc Natl Acad Sci U S A 92 (1995) 3449-3453
15. Miyanoshita A., Hara S., Sugiyama M., Asaoka A., Taniai K., Yukuhiro F., et al. Isolation and characterization of a new member of the insect defensin family from a beetle, Allomyrina dichotoma. Biochem Biophys Res Commun 220 (1996) 526-531
16. Moody J.A. Synergism testing: broth microdilution checkerboard and broth macrodilution methods. In: Isenberg H.D. (Ed). Clinical microbiology procedures handbook (1992), American Society for Microbiology Press, Washington, DC 1-28
17. Moore A.J., Devine D.A., and Bibby M.C. Preliminary experimental anticancer activity of cecropins. Pept Res 7 (1994) 265-269
18. Ohsaki Y., Gazdar A.F., Chen H.C., and Johnson B.E. Antitumor activity of magainin analogues against human lung cancer cell lines. Cancer Res 52 (1992) 3534-3538
19. Op den Kamp J.A. Lipid asymmetry in membranes. Annu Rev Biochem 48 (1979) 47-71
20. Papo N., and Shai Y. New lytic peptides based on the d,l-amphipathic helix motif preferentially kill tumor cells compared to normal cells. Biochemistry 42 (2003) 9346-9354
21. Papo N., Braunstein A., Eshhar Z., and Shai Y. Suppression of human prostate tumor growth in mice by a cytolytic d-, l-amino acid peptide: membrane lysis, increased necrosis, and inhibition of prostate-specific antigen secretion. Cancer Res 64 (2004) 5779-5786
22. Papo N., and Shai Y. Host defense peptides as new weapons in cancer treatment. Cell Mol Life Sci 62 (2005) 784-790
23. Rao L.V., Tait J.F., and Hoang A.D. Binding of annexin V to a human ovarian carcinoma cell line (OC-2008). Contrasting effects on cell surface factor VIIa/tissue factor activity and prothrombinase activity. Thromb Res 67 (1992) 517-531
24. Ross W.E., Ewig R.A., and Kohn K.W. Differences between melphalan and nitrogen mustard in the formation and removal of DNA cross-links. Cancer Res 38 (1978) 1502-1506
25. Rothman J.E., and Lenard J. Membrane asymmetry. Science 195 (1977) 743-753
26. Saido-Sakanaka H., Ishibashi J., Sagisaka A., Momotani E., and Yamakawa M. Synthesis and characterization of bactericidal oligopeptides designed on the basis of an insect anti-bacterial peptide. Biochem J 338 (1999) 29-33
27. Saido-Sakanaka H., Ishibashi J., Momotani E., Amano F., and Yamakawa M. In vitro and in vivo activity of antimicrobial peptides synthesized based on the insect defensin. Peptides 25 (2004) 19-27
28. Saido-Sakanaka H., Ishibashi J., Momotani E., and Yamakawa M. Protective effects of synthetic antibacterial oligopeptides based on the insect defensins on methicillin-resistant Staphylococcus aureus in mice. Dev Comp Immunol 29 (2005) 469-477
29. Sanderson B.J., Ferguson L.R., and Denny W.A. Mutagenic and carcinogenic properties of platinum-based anticancer drugs. Mutat Res 355 (1996) 59-70
30. Schlegel R.A., Callahan M., Krahling S., Pradhan D., and Williamson P. Mechanisms for recognition and phagocytosis of apoptotic lymphocytes by macrophages. Adv Exp Med Biol 406 (1996) 21-28
31. Schwartz R.S. Autoantibodies and normal antibodies: two sides of the same coin. Harvey Lect 81 (1985) 53-66
32. Soballe P.W., Maloy W.L., Myrga M.L., Jacob L.S., and Herlyn M. Experimental local therapy of human melanoma with lytic magainin peptides. Int J Cancer 60 (1995) 280-284
33. Sugimura M., Donato R., Kakkar V.V., and Scully M.F. Annexin V as a probe of the contribution of anionic phospholipids to the procoagulant activity of tumour cell surfaces. Blood Coagul Fibrinolysis 5 (1994) 365-373
34. Utsugi T., Schroit A.J., Connor J., Bucana C.D., and Fidler I.J. Elevated expression of phosphatidylserine in the outer membrane leaflet of human tumor cells and recognition by activated human blood monocytes. Cancer Res 51 (1991) 3062-3066
35. Verkleij A.J., Zwaal R.F., Roelofsen B., Comfurius P., Kastelijn D., and van Deenen L.L. The asymmetric distribution of phospholipids in the human red cell membrane. A combined study using phospholipases and freeze-etch electron microscopy. Biochim Biophys Acta 323 (1973) 178-193
36. Woehlecke H., Pohl A., Alder-Baerens N., Lage H., and Herrmann A. Enhanced exposure of phosphatidylserine in human gastric carcinoma cells overexpressing the half-size ABC transporter BCRP (ABCG2). Biochem J 376 (2003) 489-495
37. Wood B.L., Gibson D.F., and Tait J.F. Increased erythrocyte phosphatidylserine exposure in sickle cell disease: flow-cytometric measurement and clinical associations. Blood 88 (1996) 1873-1880
38. Xiao Y.C., Huang Y.D., Xu P.L., Zhou Z.Q., and Li X.K. Pro-apoptotic effect of cecropin AD on nasopharyngeal carcinoma cells. Chin Med J (Engl) 119 (2006) 1042-1046
39. Yamada M., Nakamura K., Saido-Sakanaka H., Asaoka A., Yamakawa M., Sameshima T., et al. Effect of modified oligopeptides from the beetle Allomyrina dichotoma on Escherichia coli infection in mice. J Vet Med Sci 66 (2004) 137-142
40. Yamada M., Nakamura K., Saido-Sakanaka H., Asaoka A., Yamakawa M., Yamamoto Y., et al. Therapeutic effect of modified oligopeptides from the beetle Allomyrina dichotoma on methicillin-resistant Staphylococcus aureus (MRSA) infection in mice. J Vet Med Sci 67 (2005) 1005-1011
41. Yamaji-Hasegawa A., and Tsujimoto M. Asymmetric distribution of phospholipids in biomembranes. Biol Pharm Bull 29 (2006) 1547-1553
42. Yasin Z., Witting S., Palascak M.B., Joiner C.H., Rucknagel D.L., and Franco R.S. Phosphatidylserine externalization in sickle red blood cells: associations with cell age, density, and hemoglobin F. Blood 102 (2003) 365-370
43. Zasloff M. Antimicrobial peptides of multicellular organisms. Nature 415 (2002) 389-395
44. Zwaal R.F., Comfurius P., and Bevers E.M. Surface exposure of phosphatidylserine in pathological cells. Cell Mol Life Sci 62 (2005) 971-988