Structure-activity relationships of pyrithiones - IPC-81 toxicity tests with the antifouling biocide zinc pyrithione and structural analogs

Green Chemistry

Volumn 6, Issue 5, 2004, Pages 259-266

  Doose, Caren A ^a,b   Ranke, Johannes ^a   Stock, Frauke ^a   Bottin Weber, Ulrike ^a   Jastorff, Bernd ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFOULING AGENT; BIOCIDE; COPPER DERIVATIVE; DISULFIDE; IRON DERIVATIVE; ORGANOTIN COMPOUND; PYRIDINE; PYRIDINE 1 OXIDE; PYRITHIONE ZINC; TRIBUTYLTIN; TRIBUTYLTIN CHLORIDE; ZINC COMPLEX;

ANIMAL CELL; ARTICLE; CELL STRAIN; CONTROLLED STUDY; LEUKEMIA CELL; METHYLATION; MOLECULAR INTERACTION; NONHUMAN; OXIDATION; RAT; RISK ASSESSMENT; STRUCTURE ACTIVITY RELATION; TOXICITY TESTING;

EID: 2542425429     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b314753c     Document Type: Article

References (51)

1. J. Sun, Q. Fernando and H. Freiser, Anal. Chem., 1964, 36(13), 2485-2488.
2. A. Albert, C. W. Rees and A. J. H. Tomlinson, Br. J. Exptl. Pathol., 1956, 37, 500-511.
3. B. L. Song, Z. S. Lu, D. Z. Niu and Y. Cao, Chin. Chem. Lett., 1990, 1(2), 117-118.
4. G. A. Hyde and J. D. Nelson Jr., Cosmet. Drug Preserv., 1984, 115-128.
5. J. G. Black and D. Howes, Clin. Toxicol., 1978, 13(1), 1-26.
6. W. B. Gibson, A. R. Jeffcoat, T. S. Turan, R. H. Wendt, P. F. Hughes and M. E. Twine, Toxicol. Appl. Pharmacol., 1982, 62(2), 237-250.
7. Olin Corporation, Harmful effects of the use of anti-fouling paints for ships: Environmental risk assessment of zinc pyrithione anti-fouling biocides, MEPC 42/5/10, International Maritime Organization, Marine Environment Protection Committee, 4th September 1998, http://www.imo.org/index.htm.
8. N. Voulvoulis, M. D. Scrimshaw and J. N. Lester, Appl. Organomet. Chem., 1999, 13(3), 135-143.
9. D. E. Audette, R. J. Fenn, J. C. Ritter, G. Polson and P. A. Turley, The Euro-Mediterranean Centre on Insular Coastal Dynamics, Costs and benefits. From antidandruff to antifoulant: a non-persistent alternative to TBT and alternative antifoulants - an international conference, Foundation for International Studies, Malta, 4-6 December 1995.
10. B. L. Barnett, H. C. Kretschmar and F. A. Hartman, Inorg. Chem., 1977, 16(8), 1834-1838.
11. PCI interview, Robert Martin, Arch Chemicals, http://www.archbiocides. com/marine/news.asp, 20-9-2002.
12. K. Goka, Environ. Res., 1999, 81(1), 81-83.
13. N. Kobayashi and H. Okamura, Mar. Pollut. Bull., 2002, 44, 748-751.
14. M. Möller, W. Adam, C. R. Saha-Möller and H. Stopper, Toxicol. Lett., 2002, 136, 77-84.
15. C. J. Chandler and I. H. Segel, Antimicrob. Agents Chemother., 1978, 14(1), 60-68.
16. A. J. Dinning, I. S. I. Al-Adham, P. Austin, M. Charlton and P. J. Collier, Lett. Appl. Microbiol., 1998, 85(1), 132-140.
17. I. S. I. Al-Adham, A. J. Dinning and I. A. Eastwood, J. Ind. Microbiol. Biotechnol., 1998, 21, 6-10.
18. A. J. Dinning, I. S. I. Al-Adham, I. M. Eastwood and P. J. Collier, Abstr. Gen. Meet. Am. Soc. Microbiol., 1995, 95, 151), ISSN: 1060-2011.
19. S. M. A. Abdel Malek, I. S. I. Al-Adham, C. L. Winder, T. E. J. Buultjens, K. M. A. Gartland and P. J. Collier, J. Appl. Microbiol., 2002, 92, 729-736.
20. W. T. Gibson, M. Chamberlain, J. F. Parsons, J. E. Brunskill, D. Leftwich, S. Lock and R. J. Safford, Food Chem. Toxicol., 1985, 23(1), 93-102.
21. E. J. Lesnefsky and J. Ye, Am. J. Physiol., 1994, 266, H384-392.
22. K. E. Dineley, J. M. Scanlon, G. J. Kress, A. K. Stout and I. J. Reynolds, Neurobiol. Dis., 2000, 7, 310-320.
23. E. Ermolayeva and D. Sanders, Appl. Environ. Microbiol., 1995, 61(9), 3385-3390.
24. C. H. Kim, J. H. Kim, S. J. Moon, K. C. Chung, C. Y. Hsu, J. T. Seo and Y. S. Ahn, Biochem. Biophys. Res. Commun., 1999, 259(3), 505-509.
25. M. Alirezaei, A. Nairn, J. Glowinski, J. Prémont and P. Marin, J. Biol. Chem., 1999, 274(45), 32433-32438.
26. R. C. Spiker Jr. and H. P. Ciuchta, Am. Ind. Hyg. Assoc. J., 1980, 41(4), 248-253.
27. G. J. Kontoghiorghes, A. Piga and A. V. Hoffbrand, FEBS Lett., 1986, 204(2), 208-212.
28. G. Imokawa and K. Okamoto, J. Soc. Cosmet. Chem., 1983, 34(1), 1-11.
29. M. M. Khattar and W. G. Salt, J. Chemother., 1993, 5, 175-177.
30. D. M. van Reyk, S. Sarel and N. H. Hunt, Int. J. Immunopharmacol., 1992, 14(5), 925-932.
31. C. Hoffman, H. Genieser, M. Veron and B. Jastorff, Bioorg. Med. Chem. Lett., 1996, 21, 2571.
32. J. Ranke, K. Möller, F. Stock, U. Bottin-Weber, J. Poczobutt, J. Hoffmann, B. Ondruschka, J. Filser and B. Jastorff, Ecotoxicol. Environ. Saf., 2003, in press 10.1016/80147-6513(03)00105-2, available at the EES website.
33. S. Ruchaud, M. Zorn, E. Davilar-Villar, H. Genieser, C. Hoffmann, B. Gjersten, S. Doeskeland, B. Jastorff and M. Lanotte, Cell. Pharmacol., 1995, 2, 127.
34. N. Lacaze, G. Gombaud-Saintonge and M. Lanotte, Leuk. Res., 1983, 7(2), 145-154.
35. B. Jastorff, R. Stoermann and U. Woelcke, Struktur-Wirkungs-Denken in der Chemie, Universitätsverlag Aschenbeck und Isensee, Bremen, Oldenburg, 2003.
36. C. Doose, Pyrithiones: From Molecular Structure to Biological Action - Implementation of the T-SAR-approach for the understanding of delicate analytes and versatile biocides, Dr. rer. nat. Dissertation, University of Bremen, Germany, 2003.
37. D. H. R. Barton, C. Chen and G. M. Wall, Tetrahedron, 1991, 47(32), 6127-6138.
38. R. Freshney, Culture of animal cells a manual of basic technique, 4 edn., Wiley-Liss. Inc., New York, 2000.
39. A. Moore, R. Gerner and H. Franklin, J. Am. Med. Assoc., 1967, 199, 519-524.
40. R. A. Jones and A. R. Katritzky, J. Chem. Soc., 1960, 2937-2942.
41. J. N. Gardner and A. R. Katritzky, J. Chem. Soc., 1957, 4375-4387.
42. B. Lynch and M. R. Smyth, Voltammetric determination of some heterocyclic mercaptans, ed. M. R. Smyth and J. G. Vos, Elsevier Science Publishers B. V., Amsterdam, The Netherlands, 1986, pp. 97-103.
43. A. F. Krivis, E. S. Gazda, G. R. Supp and M. A. Robinson, Anal. Chem., 1963, 35(8), 966-968.
44. I. Pardo, M. Angulo, R. M. Galvin and J. M. R. Mellado, Electrochim. Acta, 1996, 41(1), 133-139.
45. E. Shaw, J. Bernstein, K. Losee and W. A. Lott, J. Am. Chem. Soc., 1950, 72, 4362-4364.
46. F. Leonard, F. A. Barkley, E. V. Brown, F. E. Anderson and D. M. Green, Antibiot. Chemother., 1956, 6(4), 261-266.
47. A. Albert, C. W. Rees and A. J. H. Tomlinson, Recl. Tray. Chim., 1956, 75, 819-824.
48. P. Anastas and J. Warner, Green Chemistry - Theory and Practice, Oxford University Press, Oxford, UK, 2000.
49. T. Madsen, L. Samsoe-Petersen, K. Gustavson and D. Rasmussen, Environmental project: Ecological assessment of antifouling biocides and nonbiocidal antifouling paints; The Danish Environmental Protection Agency, DHI Water & Environment, Miliøstyrelsen, Environmental project: No. 531, 2000.
50. J. D. Nelson and G. A. Hyde, Cosmet. Toiletries, 1981, 96(3), 87-90.
51. T. P. Schultz, T. Nilsson and D. D. Nicholas, Wood Fiber Sci., 2000, 32(3), 346-353.