Impact of the pectenotoxin C-43 oxidation degree on its cytotoxic effect on rat hepatocytes

Chemical Research in Toxicology

Volumn 23, Issue 3, 2010, Pages 504-515

  Espiña, Begoña ^a   Louzao, M Carmen ^a   Ares, Isabel R ^a   Fonfrý́a, Eva S ^a   Vilariño, Natalia ^a   Vieytes, Mercedes R ^a   Yasumoto, Takeshi ^b   Botana, Luis M ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b JAPAN FOOD RESEARCH LABORATORIES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIN; CARBOXYLIC ACID DERIVATIVE; PECTENOTOXIN DERIVATIVE; TOXIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL CELL CULTURE; ARTICLE; CELL IMMORTALIZATION; CELL LINE; CELL STRAIN CACO 2; CELL STRUCTURE; CELL VIABILITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOSKELETON; CYTOTOXICITY; DOSE RESPONSE; EPITHELIUM CELL; LIVER CELL; NONHUMAN; OXIDATION; RAT;

ACTINS; ANIMALS; CELL LINE; CELL SURVIVAL; CELLS, CULTURED; CYTOSKELETON; CYTOTOXINS; FURANS; HEPATOCYTES; LACTONES; MALE; MARINE TOXINS; OXIDATION-REDUCTION; PECTINIDAE; PYRANS; RATS; RATS, SPRAGUE-DAWLEY;

CHLAMYS NIPPONENSIS; MIZUHOPECTEN YESSOENSIS; MUS; RATTUS;

EID: 77949404772     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx9002337     Document Type: Article

References (49)

1. Daiguji, M., Satake, M., James, K. J., Bishop, A. G., MacKenzie, L., Naoki, H., and Yasumoto, T. (1998) Structures of new pectenotoxin analogs, pectenotoxin-2 seco acid and 7-epi-2 seco acid, isolated from a dinoflagelate and greenshell mussels. Chem. Lett. 7, 653-654.
2. Draisci, R., Lucentini, L., Giannetti, L., Boria, P., and Poletti, R. (1996) First report of pectenotoxin-2 (PTX-2) in algae (Dinophysis fortii) related to seafood poisoning in Europe. Toxicon 34, 923-935.
3. James, K. J., Bishop, A. G., Draisci, R., Palleschi, L., Marchiafava, C., Ferretti, E., Satake, M., and Yasumoto, T. (1999) Liquid chromatographic methods for the isolation and identification of new pectenotoxin-2 analogues from marine phytoplankton and shellfish. J. Chromatogr., A 844, 53-65.
4. Lee, J. S., Yanagi, Y., Kenma, R., and Yasumoto, T. (1987) Fluorometric determination of diarrhetic shellfish toxins by high performance liquid chromatography. Agric. Biol. Chem. 51, 877-881.
5. Miles, C. O., Wilkins, A. L., Munday, R., Dines, M. H., Hawkes, A. D., Briggs, L. R., Sandvik, M., Jensen, D. J., Cooney, J. M., Holland, P. T., Quilliam, M. A., MacKenzie, A. L., Beuzenberg, V., and Towers, N. R. (2004) Isolation of pectenotoxin-2 from Dinophysis acuta and its conversion to pectenotoxin-2 seco acid, and preliminary assessment of their acute toxicities. Toxicon 43, 1-9.
6. Pavela-Vrancic, M., Mestrovic, V., Marasovic, I., Gillman, M., Furey, A., and James, K. K. (2001) The occurrence of 7-epi-pectenotoxin-2 seco acid in the coastal waters of the central Adriatic (Kastela Bay). Toxicon 39, 771-779.
7. Suzuki, T., Mitsuya, T., Matsubara, H., and Yamasaki, M. (1998) Determination of pectenotoxin-2 after solid-phase extraction from seawater and from the dinoflagellate Dinophysis fortii by liquid chromatography with electrospray mass spectrometry and ultraviolet detection. Evidence of oxidation of pectenotoxin-2 to pectenotoxin-6 in scallops. J. Chromatogr., A 815, 155-160.
8. Vale, P., and de M Sampayo, M. A. (2002) Pectenotoxin-2 seco acid, 7-epi-pectenotoxin-2 seco acid and pectenotoxin-2 in shellfish and plankton from Portugal. Toxicon 40, 979-987.
9. MacKenzie, L., Holland, P., McNabb, P., Beuzenberg, V., Selwood, A., and Suzuki, T. (2002) Complex toxin profiles in phytoplankton and Greenshell mussels (Perna canaliculus), revealed by LC-MS/MS analysis. Toxicon 40, 1321-1330.
10. Miles, C. O. (2007) Pectenotoxins, in Phycotoxins: Chemistry and Biochemistry (Botana, L. M., Ed.) pp 159-186, Blackwell Publishers, Ames, IA.
11. Ito, E., Suzuki, T., Oshima, Y., and Yasumoto, T. (2008) Studies of diarrhetic activity on pectenotoxin-6 in the mouse and rat. Toxicon 51, 707-716.
12. Krock, B., Tillmann, U., Selwood, A. I., and Cembella, A. D. (2008) Unambiguous identification of pectenotoxin-1 and distribution of pectenotoxins in plankton from the North Sea. Toxicon 52, 927-935.
13. Yasumoto, T., Murata, M., and Lee, J. (1989) Polyether Toxins Produced by Dinoflagellates, in Mycotoxins and Phycotoxins '88 (Natori, S., Hashimoto, K., and Ueno, Y., Eds.) pp 375-382, Elsevier, Amsterdam.
14. Yasumoto, T., Murata, M., Oshima, Y., Matsumoto, G. K., and Clardy, J. (1984) Diarrhetic Shellfish Poisoning, in Seafood Toxins (Ragelis, E. P., Ed.) pp 207-214, American Chemical Society, Washington, DC.
15. Suzuki, T., Walter, J. A., LeBlanc, P., MacKinnon, S., Miles, C. O., Wilkins, A. L., Munday, R., Beuzenberg, V., MacKenzie, A. L., Jensen, D. J., Cooney, J. M., and Quilliam, M. A. (2006) Identification of pectenotoxin-11 as 34S-hydroxypectenotoxin-2, a new pectenotoxin analogue in the toxic dinoflagellate Dinophysis acuta from New Zealand. Chem. Res. Toxicol. 19, 310-318.
16. Ares, I. R., Louzao, M. C., Espina, B., Vieytes, M. R., Miles, C. O., Yasumoto, T., and Botana, L. M. (2007) Lactone ring of pectenotoxins: a key factor for their activity on cytoskeletal dynamics. Cell Physiol. Biochem. 19, 283-292.
17. Sasaki, K., Wright, J. L., and Yasumoto, T. (1998) Identification and characterization of pectenotoxin (PTX) 4 and PTX7 as spiroketal stereoisomers of two previously reported pectenotoxins. J. Org. Chem. 63, 2475-2480.
18. Hori, M., Matsuura, Y., Yoshimoto, R., Ozaki, H., Yasumoto, T., and Karaki, H. (1999) Actin depolymerizing action by marine toxin, pectenotoxin-2. Nippon Yakurigaku Zasshi 114 (1), 225P-229P.
19. Allingham, J. S., Miles, C. O., and Rayment, I. (2007) A structural basis for regulation of actin polymerization by pectenotoxins. J. Mol. Biol. 371, 959-970.
20. Espina, B., and Rubiolo, J. A. (2008) Marine toxins and the cytoskeleton: pectenotoxins, unusual macrolides that disrupt actin. Febs J 275, 6082-6088.
21. Chae, H. D., Choi, T. S., Kim, B. M., Jung, J. H., Bang, Y. J., and Shin, D. Y. (2005) Oocyte-based screening of cytokinesis inhibitors and identification of pectenotoxin-2 that induces Bim/Bax-mediated apoptosis in p53-deficient tumors. Oncogene 24, 4813-4819.
22. Fladmark, K. E., Serres, M. H., Larsen, N. L., Yasumoto, T., Aune, T., and Doskeland, S. O. (1998) Sensitive detection of apoptogenic toxins in suspension cultures of rat and salmon hepatocytes. Toxicon 36, 1101-1114.
23. Kim, M. O., Moon, D. O., Heo, M. S., Lee, J. D., Jung, J. H., Kim, S. K., Choi, Y. H., and Kim, G. Y. (2008) Pectenotoxin-2 abolishes constitutively activated NF-kappaB, leading to suppression of NFkappaB related gene products and potentiation of apoptosis. Cancer Lett. 271, 25-33.
24. Louzao, M. C., Espina, B., Vieytes, M. R., Vega, F. V., Rubiolo, J. A., Baba, O., Terashima, T., and Botana, L. M. (2008) Fluorescent glycogen formation with sensibility for in vivo and in vitro detection. Glycoconjugate J. 25, 503-510.
25. Pazo, J. A., Rodriguez, M. E., Vega, F., De la Cruz, L., Guibert, E., Mediavilla, M. G., Furno, G., and Rodriguez, J. V. (2002) Hepatocytes after cold storage in University of Wisconsin Solution: a tool to study the effects of hypothermic preservation. Cell PreserV. Technol. 1, 189-199.
26. Barbini, L., Gonzalez, R., Dominguez, F., and Vega, F. (2006) Apoptotic and proliferating hepatocytes differ in prothymosin alpha expression and cell localization. Mol. Cell. Biochem. 291, 83-91.
27. Espina, B., Louzao, M. C., Ares, I. R., Cagide, E., Vieytes, M. R., Vega, F. V., Rubiolo, J. A., Miles, C. O., Suzuki, T., Yasumoto, T., and Botana, L. M. (2008) Cytoskeletal toxicity of pectenotoxins in hepatic cells. Br. J. Pharmacol. 155, 934-944.
28. Ahmed, S. A., Gogal, R. M., Jr., and Walsh, J. E. (1994) A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: an alternative to [3H]thymidine incorporation assay. J. Immunol. Methods 170, 211-224.
29. Espina, B., Cagide, E., Louzao, M. C., Fernandez, M. M., Vieytes, M. R., Katikou, P., Villar, A., Jaen, D., Maman, L., and Botana, L. M. (2009) Specific and dynamic detection of palytoxins by in vitro microplate assay with human neuroblastoma cells. Biosci. Rep. 29, 13-23.
30. Yasumoto, T., Murata, M., Oshima, Y., Sano, M., Matsumoto, G. K., and Clardy, J. (1985) Diarrhetic shellfish toxins. Tetrahedron 1, 1019.
31. Suzuki, T., Jin, T., Shirota, Y., Mitsuya, T., Okumura, Y., and Kamiyama, T. (2005) Quantification of lipophilic toxins associated with diarrhetic shellfish poisoning in Japanese bivalves by liquid chromatography-mass spectrometry and comparison with mouse bioassay. Fish. Sci. 71, 1370.
32. Suzuki, T., and Yasumoto, T. (2000) Liquid chromatographyelectrospray ionization mass spectrometry of the diarrhetic shellfishpoisoning toxins okadaic acid, dinophysistoxin-1 and pectenotoxin-6 in bivalves. J. Chromatogr., A 874, 199-206
33. EC. (2002) Commission Decision of 15 March 2002. Laying down rules for the implementation of Council Directive 91/492/EEC as regards the maximum levels and the methods of analysis of certain marine biotoxins in bivalve molluscs, echinoderms, tunicates and marine gastropods, Off. J. Eur. Commun. L75, 62-63.
34. FAO/IOC/WHO. (2004) Report of the joint FAO/IOC/WHO ad hoc expert consultation on biotoxins in bivalve molluscs Oslo, Norway.
35. Leira, F., Cabado, A. G., Vieytes, M. R., Roman, Y., Alfonso, A., Botana, L. M., Yasumoto, T., Malaguti, C., and Rossini, G. P. (2002) Characterization of F-actin depolymerization as a major toxic event induced by pectenotoxin-6 in neuroblastoma cells. Biochem. Pharmacol. 63, 1979-1988.
36. Cagide, E., Louzao, M. C., Ares, I. R., Vieytes, M. R., Yotsu-Yamashita, M., Paquette, L. A., Yasumoto, T., and Botana, L. M. (2007) Effects of a synthetic analog of polycavernoside A on human neuroblastoma cells. Cell Physiol. Biochem. 19, 185-194.
37. Louzao, M. C., Cagide, E., Vieytes, M. R., Sasaki, M., Fuwa, H., Yasumoto, T., and Botana, L. M. (2006) The sodium channel of human excitable cells is a target for gambierol. Cell Physiol. Biochem. 17, 257-268.
38. Weigmann, A., Corbeil, D., Hellwig, A., and Huttner, W. B. (1997) Prominin, a novel microvilli-specific polytopic membrane protein of the apical surface of epithelial cells, is targeted to plasmalemmal protrusions of non-epithelial cells. Proc. Natl. Acad. Sci. U.S.A. 94, 12425-12430.
39. Yonemura, S., Itoh, M., Nagafuchi, A., and Tsukita, S. (1995) Cellto-cell adherens junction formation and actin filament organization: similarities and differences between non-polarized fibroblasts and polarized epithelial cells. J. Cell Sci. 108 (Pt. 1), 127-142.
40. Jung, J. H., Sim, C. J., and Lee, C. O. (1995) Cytotoxic compounds from a two-sponge association. J. Nat. Prod. 58, 1722-1726.
41. Moon, D. O., Kim, M. O., Kang, S. H., Lee, K. J., Heo, M. S., Choi, K. S., Choi, Y. H., and Kim, G. Y. (2008) Induction of G2/M arrest, endoreduplication, and apoptosis by actin depolymerization agent pextenotoxin-2 in human leukemia cells, involving activation of ERK and JNK. Biochem. Pharmacol. 76, 312-321.
42. Hanahan, D., and Weinberg, R. A. (2000) The hallmarks of cancer. Cell 100, 57-70.
43. Perron, F., and Albizati, K. F. (1989) Chemistry of spiroketals. Chem. ReV. 89, 1617-1661.
44. Ares, I. R., Louzao, M. C., Vieytes, M. R., Yasumoto, T., and Botana, L. M. (2005) Actin cytoskeleton of rabbit intestinal cells is a target for potent marine phycotoxins. J. Exp. Biol. 208, 4345-4354.
45. Alrefai, W. A., and Gill, R. K. (2007) Bile acid transporters: structure, function, regulation and pathophysiological implications. Pharm. Res. 24, 1803-1823.
46. Runnegar, M. T., Gerdes, R. G., and Falconer, I. R. (1991) The uptake of the cyanobacterial hepatotoxin microcystin by isolated rat hepatocytes. Toxicon 29, 43-51.
47. Dawson, R. M. (1998) The toxicology of microcystins. Toxicon 36, 953-962.
48. Torchia, E. C., Shapiro, R. J., and Agellon, L. B. (1996) Reconstitution of bile acid transport in the rat hepatoma McArdle RH-7777 cell line. Hepatology 24, 206-211.
49. Mereish, K. A., and Solow, R. (1990) Effect of antihepatotoxic agents against microcystin-LR toxicity in cultured rat hepatocytes. Pharm. Res. 7, 256-259.