The cyanobacterial cyclic lipopeptides puwainaphycins F/G are inducing necrosis via cell membrane permeabilization and subsequent unusual actin relocalization

Chemical Research in Toxicology

Volumn 25, Issue 6, 2012, Pages 1203-1211

  Hrouzek, Pavel ^a,b   Kuzma, Marek ^a   Černyý, Jan ^c   Novák, Petr ^a,c   Fisšer, Radovan ^c   Sšimek, Petr ^d   Lukesšová, Alena ^e   Kopeckyý, Jiršiý ^a,b  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

^d INSTITUTE OF ENTOMOLOGY   (Czech Republic)

^e INSTITUTE OF SOIL BIOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 3 AMINO 4 METHYL TETRADECANOIC ACID; ACTIN; BETA AMINO ACID; CALCIUM; FATTY ACID; GLUTAMINE; IONOMYCIN; LIPOPEPTIDE; PUWAINAPHYCIN F; PUWAINAPHYCIN G; THREONINE; TYROSINE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANIMAL CELL; ARTICLE; CALCIUM CELL LEVEL; CELL DEATH; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CELL NUCLEUS; CELL STRUCTURE; CONTROLLED STUDY; FEMALE; HELA CELL; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PROTEIN LOCALIZATION;

ACTIN CYTOSKELETON; ACTINS; ANTINEOPLASTIC AGENTS; CALCIUM; CELL DEATH; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CYANOBACTERIA; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; LIPOPEPTIDES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862547236     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx300044t     Document Type: Article

References (23)

1. MacKintosch, C., Beattie, K. A., Klumpp, S., Cohen, P., and Codd, G. A. (1990) Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants FEBS Lett. 264, 187-192 (Pubitemid 20169213)
2. Ohta, T., Sueoka, E., Iida, N., Komori, A., Sugamuna, M., Nishiwaki, R., Tatematus, M., Kim, S. J., Carmichael, W. W., and Fujiki, H. (1994) Nodularin, a potent inhibitor of protein phosphatases 1 and 2A is a new environmental carcinogen in male F344 rat liver Cancer Res. 54, 6402-6406
3. Yoshizawa, S., Matsushima, R., Watanabe, M. F., Harada, K. I., Ichihara, A., Carmichael, W. W., and Fujiki, H. (1990) Inhibition of protein phosphatases by microcystin and nodularin associated with hepatotoxicity J. Cancer Res. Clin. Oncol. 116, 609-614 (Pubitemid 20386365)
4. Welker, M. and vön Dohren, H. (2006) Cyanobacterial peptides - Nature's own combinatorial biosynthesis Fems Microbiol. Rev. 30, 530-563 (Pubitemid 43855766)
5. Welker, M., Marsšálek, B., Sšejnohová, L., and vön Dohren, H. (2006) Detection and identification of oligopeptides in Microcystis (cyanobacteria) colonies: Toward an understanding of metabolic diversity Peptides 27, 2090-2103 (Pubitemid 44189619)
6. Hrouzek, P., Tomek, P., Lukesšová, A., Urban, J., Voloshko, L., Pushparaj, B., Lukavskyý, J., Sštys, D., and Kopeckyý, J. (2011) Cytotoxicity and Secondary Metabolites Production in Terrestrial Nostoc Strains, Originating From Different Climatic/Geographic Regions and Habitats: Is Their Cytotoxicity Environmentally Dependent? Environ. Toxicol. 25, 345-358
7. Chorus, I. and Bartram, J. (1999) Toxic Cyanobacteria in Water: A Guide to their Public Health Consequences. Monitoring and Management, pp 416, E & FN Spon, London.
8. Liu, L. and Rein, S. (2010) New peptides isolated from Lyngbya species: A review Mar. Drugs 8, 1817-1837
9. Maru, N., Ohno, O., and Uemura, D. (2010) Lyngbyacyclamides A and B, novel cytotoxic peptides from marine cyanobacteria Lyngbya sp Tetrahedron Lett. 51, 6384-6387
10. Moon, S. S., Chen, J. L., Moore, R. E., and Patterson, G. M. L. (1992) Calophycin A, a fungicidal cyclic decapeptide from the terrestrial blue-green alga Calothrix fusca J. Org. Chem. 57, 1097-1103
11. Plaza, A. and Bewley, C. A. (2006) Largamides A-H, unusual cyclic peptides from the marine cyanobacterium Oscillatoria sp J. Org. Chem. 71, 6898-6907 (Pubitemid 44645667)
12. MacMillan, J. B., Ernst-Russell, M. A., De Ropp, J. S., and Molinski, T. F. (2002) Lobocyclamides A-C, lipopeptides from a cryptic cyanobacterial mat containing Lyngbya confervoides J. Org. Chem. 67, 8210-8215 (Pubitemid 35332001)
13. An, T. Y., Kumar, T. K. S., Wang, M. L., Liu, L., Lay, J. O., Liyanage, R., Berry, J., Gantar, M., Marks, V., Gawley, R. E., and Rein, K. S. (2007) Structures of pahayokolides A and B, cyclic peptides from a Lyngbya sp J. Nat. Prod. 70, 730-735 (Pubitemid 46953590)
14. Berry, J. P., Gantar, M., Gawley, R. E., Wang, M. L., and Rein, K. S. (2004) Pharmacology and toxicology of pahayokolide A, a bioactive metabolite from a freshwater species of Lyngbya isolated from the Florida Everglades Comp. Biochem. Physiol., Part C: Toxicol. Pharmacol. 139, 231-238 (Pubitemid 40430777)
15. Gregson, J. M., Chen, J. L., Patterson, G. M. L., and Moore, R. E. (1992) Structures of puwainaphycines Tetrahedron 48, 3727-3734
16. Moore, R. E., Bornemann, V., Niemczura, W. P., Gregson, J. M., Chen, J. L., Norton, T. R., Patterson, G. M. L., and Helms, G. (1989) Puwainaphycin C, a cardioactive cyclic peptide from the blue-green alga Anabaena BQ-16-1. Use of two-dimensional 13C-13C and 13C-15N correlation spectroscopy in sequencing of amino acid units J. Am. Chem. Soc. 111, 6128-6132 (Pubitemid 19203126)
17. Sšimek, P., Husšek, P., and Zahradniýcš ková, H. (2008) Gas chromatographic-mass spectrometric analysis of biomarkers related to folate and cobalamin status in human serum after dimercaptopropanesulfonate reduction and heptafluorobutyl chloroformate derivatization Anal. Chem. 80, 5776-582
18. Zahradniýcšková, H., Husšek, P., and Sšimek, P. (2009) GC separation of amino acid enantiomers via derivatization with heptafluorobutyl chloroformate and Chirasil-L-Val column J. Sep. Sci. 32, 3919-3924
19. König, W. A., Steinbach, E., and Phosgene, E. K. (1984) A versatile reagent for enantiomer separation by capillary gas chromatography J. Chromatogr. A 301, 129-135
20. Mosmann, T. (1983) Rapid colorimetric assays for cellular growth and survival - Application to proliferation and cytotoxicity assays J. Immunol. Methods 65, 55-63 (Pubitemid 14203433)
21. Hisem, D., Hrouzek, P., Tomek, P., Tomsšiýcš ková, J., Zapomešlová, E., Skácelová, K., Lukesšová, A., and Kopeckyý, J. (2011) Cyanobacterial cytotoxicity versus toxicity to brine shrimp Artemia salina Toxicon 57, 76-83
22. Bacallao, R., Garfinkel, A., Monke, S., Zampighi, G., and Mandel, L. J. (1994) ATP depletion: a novel method to study junctional properties in epithelial tissues J. Cell. Sci. 107, 3301-3313
23. Du, J., Zhang, L. J., Yang, Y., Li, W. X., Chen, L., Ge, Y. B., Sun, C. Q., Zhu, Y. C., and Gu, L. (2010) ATP Depletion-induced Actin Rearrangement Reduces Cell Adhesion via p38 MAPK-HSP27 Signaling in Renal Proximal Tubule Cells Cell. Physiol. Biochem. 25, 501-510