Cytotoxic and genotoxic effects of tambjamine D, an alkaloid isolated from the nudibranch Tambja eliora, on Chinese hamster lung fibroblasts

Chemico-Biological Interactions

Volumn 174, Issue 3, 2008, Pages 155-162

  Cavalcanti, Bruno C ^a   Júnior, Hélio V N ^a   Seleghim, Mirna H R ^b   Berlinck, Roberto G S ^b   Cunha, Geanne M A ^a   Moraes, Manoel O ^a   Pessoa, Claudia ^a  

^a FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Comet assay; Micronucleus test; Oxidative stress; Tambjamine D

Indexed keywords

4 METHOXYPYRROLE DERIVATIVE; ACRIDINE ORANGE; ALKALOID DERIVATIVE; ETHIDIUM BROMIDE; NATURAL PRODUCT; NITRATE; NITRITE; REACTIVE OXYGEN METABOLITE; TAMBJAMINE D; THIOBARBITURIC ACID REACTIVE SUBSTANCE; TRYPAN BLUE;

ANIMAL CELL; ANIMAL EXPERIMENT; APOPTOSIS; ARTICLE; CELL VIABILITY; CHINESE HAMSTER; COMET ASSAY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DNA STRAND BREAKAGE; DRUG ISOLATION; GENOTOXICITY; HEMOLYSIS; LUNG FIBROBLAST; MARINE SPECIES; MEMBRANE DAMAGE; MICRONUCLEUS; MICRONUCLEUS TEST; MOUSE; NONHUMAN; OXIDATIVE STRESS; TAMBJA ELIORA;

ALKALOIDS; ANIMALS; APOPTOSIS; BIOLOGICAL PRODUCTS; CELL MEMBRANE; CELL SURVIVAL; CRICETINAE; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; FIBROBLASTS; GASTROPODA; LUNG; MICRONUCLEI, CHROMOSOME-DEFECTIVE; MICRONUCLEUS TESTS; MUTAGENS;

CRICETULUS GRISEUS; TAMBJA;

EID: 48649110366     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2008.05.029     Document Type: Article

References (50)

1. Ireland C.M., Roll D.M., Molinski T.F., McKee T.C., Zabriske T.M., and Swersey J.C. Uniqueness of marine environment: categories of marine natural products from invertebrates. In: Fautin D.G. (Ed). Biomedical Importance of Marine Organisms (1988), California Academy of Sciences, San Francisco, CA 41-57
2. Carté B.K. Biomedical Potential of Marine Natural Products: marine organisms are yelding novel molecules for use in basic research and medical applications. BioScience 46 (1996) 271-286
3. Kobayashi J. Pharmacologically active metabolites from symbiotic microalgae in okinawan marine invertebrates. J. Nat. Prod. 52 (1989) 225-238
4. Schmits F.J., and Yasumoto T. The 1990 United States-Japan seminar on bioorganic marine chemistry, meeting report. J. Nat. Prod. 54 (1991) 1469-1490
5. Stingl J., Andersen R.J., and Emerman J.T. In vitro screening of crude extracts and pure metabolites obtained from marine invertebrates for the treatment of breast cancer. Cancer Chemother. Pharmacol. 30 (1992) 401-406
6. König G.M., and Wright A.D. Marine natural products research: current directions and future potential. Planta Med. 62 (1996) 193-211
7. Frenz J.L., Kohl A.C., and Kerr R.G. Marine natural products as therapeutic agents. Part II. Expert Opin. Ther. Pat. 14 (2004) 17-33
8. Blunt J.W., Coop B.R., and Munro M.H.G. Marine natural products (review article). Nat. Prod. Rep. 22 (2005) 15-61
9. Boger D.L., and Patel M. Total synthesis of prodigiosin, prodigiosene, and desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes and development of an effective palladium(II)-promoted 2,2′-bipyrrole coupling procedure. J. Org. Chem. 53 (1988) 1405-1415
10. D'Alessio R., Bargiotti A., Carlini O., Collota F., Ferrari M., Gnocchi P., Isetta A., Mongelli N., Motta P., Rossi A., Rossi M., Tibolla M., and Vanotti E. Synthesis and immunosuppressive activity of novel prodigiosin derivatives. J. Med. Chem. 43 (2000) 2557-2565
11. Carté B., and Faulkner D.J. Defensive metabolites from three nembrothid nudibranchs. J. Org. Chem. 48 (1983) 2314-2318
12. Fusetani N. Marine metabolites which inhibit development of echinoderm embryos. In: Scheur P.J. (Ed). Biorganic Marine Chemistry (1987), Springer-Verlarg, Berlin and Heidelberg 61-92
13. Granato A.C., de Oliveira J.H.H.L., Seleghim M.H.R., Berlinck R.G.S., Macedo M.L., Ferreira A.G., da Rocha R.M., Hajdu E., Peixinho S., Pessoa C., Moraes M.O., and Cavalcanti B.C. Natural products from the ascidian Botrylloides giganteum, from the sponges Verongula gigantea, Ircinia felix, Cliona delitrix and from the nudibranch Tambja eliora, from the brazilian coastline. Quím. Nova 28 (2005) 192-198
14. Melvin M.S., Ferguson D.C., Lindquist N., and Manderville R.A. DNA binding by 4-methoxypyrrolic natural products. Preference for intercalation at AT sites by tambjamine E and prodigiosin. J. Org. Chem. 64 (1999) 6861-6869
15. Melvin M.S., Wooton K.E., Rich C.C., Saluta G.R., Kucera G.L., Lindquist N., and Manderville R.A. Copper-nuclease efficiency correlates with cytotoxicity for the 4-methoxypyrrolic natural products. J. Inorg. Biochem. 87 (2001) 129-135
16. McCoy E.C., Rosenkranz E.J., Petrullo L.A., and Rosenkranz H.S. Frameshift mutations: relative roles of simple intercalation and of adduct formation. Mutat. Res. 90 (1981) 21-30
17. Ashby J., and Paton D. The influence of chemical structure on the extend and sites of carcinogens and 55 different human carcinogen exposures. Mutat. Res. 286 (1993) 3-74
18. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 16 (1983) 55-63
19. Berlinck R.G.S., Ogawa C.A., Almeida A.M.P., Andrade M.A.S., Malpezzi E.L.A., Costa L.V., Hajdu E.M., and Freitas J.C. Chemical and pharmacological characterization of halitoxin from Amphimedon viridis (PORIFERA) from the southeastern Brazilian coast. Comp. Biochem. Physiol. 115C (1996) 155-163
20. Green L.C., Tannenbaum S.R., and Goldman P. Nitrate synthesis in the germfree and conventional rats. Science 212 (1981) 56-58
21. Draper H.H., and Hadely M. Malondialdehyde determination as an index of lipid peroxidation. Methods Enzymol. 186 (1990) 421-431
22. Singh N.P., McCoy M.T., Tice R.R., and Scheider E.L. A simple technique for quantification of low levels of DNA damage in individual cells. Exp. Cell Res. 75 (1988) 184-191
23. Hartmann A., and Speit G. The contribution of cytotoxicity to DNA-effects in the single cell gel test (comet assay). Toxicol. Lett. 90 (1997) 183-188
24. Collins A.R., Ai-guo M., and Duthie S.J. The kinetics of repair of oxidative DNA damage (strand breaks and oxidized pyrimidines) in human cells. Mutat. Res. 336 (1995) 69-77
25. Silva J., Freitas T.R.O., Heuser V., Marinho J.R., and Erdtmann B. Genotoxicity biomonitoring in coal regions using wild rodent Ctenomys torquatus by Comet assay and micronucleus test. Environ. Mol. Mutagen. 35 (2000) 270-278
26. Matsuoka A., Yamazaki N., Suzuki T., Hayashi M., and Sofuni T. Evaluation of the micronucleus test using a Chinese hamster cell line as an alternative to the conventional in vitro chromosomal aberration test. Mutat. Res. 272 (1992) 223-236
27. Bonacker D., Stoiber T., Wang M., Bohm K.J., Prots I., Unger E., Their R., Bolt H.M., and Degen G.H. Genotoxicity of inorganic mercury salts based on disturbed microtubule function. Arch. Toxicol. 78 (2004) 575-583
28. Fenech M. The in vitro micronucleus technique. Mutat. Res. 455 (2000) 81-95
29. McGahon A.J., Martin S.M., Bissonnette R.P., Mahboubi A., Shi Y., Mogil R.J., Nishioka W.K., and Green D.R. The end of (cell) line: methods for the study of apoptosis in vitro. Methods Cell Biol. 46 (1995) 153-185
30. Berlinck R.G.S., Hajdu E., Rocha R., Oliveira J.H.H.L., Hernandez I.L.C., Seleghim M.H.R., Granato A.C., Almeida E.V.R., Nunez C.V., Muricy G., Peixinho S., Pessoa C., Moraes M.O., Cavalcanti B.C., Nascimento G.G.F., Thiemann O., Silva M., Souza A.O., Silva C.L., and Minarini P.R.R. Challenges and rewards of research in marine natural products chemistry in Brazil. J. Nat. Prod. 67 (2004) 510-522
31. Bradley M., Bhuyan B., Francis M.C., Langenbach R., Peterson A., and Huberman E. Mutagenesis by chemical agents in V79 Chinese hamster cells: a review and analysis of literature. Mutat. Res. 87 (1981) 81-142
32. Renzi D., Valtonila M., and Foster R. The evaluation of a multi-endpoint cytotoxicity assay system. ATLA 21 (1993) 89-96
33. Fornelli F., Minervini F., and Logrieco A. Cytotoxicity of fungal metabolites to lepidopteran (Spodoptera frugiperda) cell line (SF-9). J. Invertebr. Pathol. 85 (2004) 74-79
34. Canicatti C. Hemolysins: pore-forming proteins in invertebrates. Experientia 46 (1990) 239-244
35. Andrews M., Garle M., and Clothier R. Reduction of the new tetrazolium dye in cultured rat hepatocytes and liver fraction. Toxicol. In Vitro 25 (1997) 641-653
36. Melvin M.S., Calcutt M.W., Noftle R.E., and Manderville R.A. Influence of the A-ring on the redox and nuclease properties of the prodigiosins: importance of the bipyrrole moiety in oxidative DNA cleavage. Chem. Res. Toxicol. 15 (2002) 742-748
37. Ko F.N., Cheng Z.H., Lin C.N., and Teng C.M. Scavenger and antioxidant properties of prenylflavones isolated from Artocarpus heterophyllus. Free Radical Biol. Med. 25 (1998) 160-168
38. Poulsen H.E. Oxidative DNA modifications. Exp. Toxicol. Pathol. 57 (2005) 161-169
39. Hartmann A., Plappert U., Poetter F., and Sutter W. Comparative study with the alkaline Comet assay and the chromosome aberration test. Mutat. Res. 536 (2003) 27-38
40. Fairbairn D.W., Walaker G.C., Olive P.L., and O'Neill K.L. The Comet assay: a comprehensive review. Mutat. Res. 339 (1995) 37-59
41. Collins A.R. The comet assay for DNA damage and repair. Mol. Biotechnol. 26 (2004) 249-261
42. Fenech M., and Morley A. Solutions to the kinetic problem in the micronucleus test. Cytobios 43 (1985) 233-246
43. Kirsch-Volders M. Towards a validation of the micronucleus test. Mutat. Res. 392 (1997) 1-4
44. Mitchell I., and Combes R. In vitro genotoxicity and cell transformation assessment. In: Castell J.V., and Gmez-Lechn M.J. (Eds). In Vitro Methods in Pharmaceutical Research (1997), Academic Press Inc., California 317-352
45. Snyder R.D. Assessment of atypical DNA intercalating agents in biological and in silico systems. Mutat. Res. 623 (2007) 72-82
46. Hearn W., Medina-Castro J., and Elson M.K. Colour change of prodigiosin. Nature 220 (1968) 170-171
47. Rizzo V., Morelli A., Pinciroli V., Sciangula D., and D'Alessio R. Equilibrium and kinetics of rotamer interconversion in immunosuppressant prodigiosin derivatives in solution. J. Pharm. Sci. 88 (1999) 73-78
48. Suzuki H.T., Ikeda T., Yamagishi T., Nakaike S., Nakane S., and Ohsawa M. Efficient induction of chromosome-type aberrations by topoisomerase II inhibitors closely associated with stabilization of the cleavable complex in cultured fibroblastic cells. Mutat. Res. 328 (1995) 151-161
49. Sortibrán A.N.C., Téllez M.G.O., and Rodríguez-Arnaiz R.R. Gentotoxic profile of inhibitors of topoisomerase I (camptothecin) and II (etoposide) in a mitotic recombination and sex-chromosome loss somatic eye assay of Drosophila melanogaster. Mutat. Res. 604 (2006) 83-90
50. Xiao J.X., Huang G.Q., Zhu C.P., Ren D.D., and Zhang S.H. Morphological study on apoptosis Hela cells induced by soyasaponis. Toxicol. In Vitro 21 (2007) 820-826