Synergism between the toxicity of chlorophenols and iron complexes

Environmental Toxicology and Chemistry

Volumn 26, Issue 2, 2007, Pages 218-224

  Levy, Smadar ^a   Shechtman, Svetlana ^a   Zhu, Ben Zhan ^a   Stadtman, Earl R ^b   Stadler, Richard ^c   Chevion, Mordechai ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b NATIONAL HEART LUNG AND BLOOD INSTITUTE   (United States)

^c NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Bacterial survival; Pentachlorophenol; Phase partitioning; Protein carbonyl content; Ternary complex

Indexed keywords

AIR POLLUTION; BACTERIA; ESCHERICHIA COLI; IRON COMPOUNDS;

BACTERIAL SURVIVAL; PENTACHLOROPHENOL; PHASE PARTITIONING; PROTEIN CARBONYL CONTENT; TERNARY COMPLEX;

PHENOLS;

1,10 PHENANTHROLINE; BIOCIDE; CHLOROPHENOL; COPPER COMPLEX; IRON COMPLEX; TRANSITION ELEMENT;

BACTERIUM; CHLOROPHENOL; GROWTH RESPONSE; IRON; POLLUTION EXPOSURE; SUBLETHAL EFFECT; SURVIVAL; SYNERGISM; TOXICITY TEST;

ARTICLE; BACTERIAL GROWTH; BACTERIAL SURVIVAL; CELL DEATH; CONTROLLED STUDY; CYTOTOXICITY; ENVIRONMENTAL EXPOSURE; ESCHERICHIA COLI; MODEL; NONHUMAN; PH; PHASE PARTITIONING; POLLUTANT; PRIORITY JOURNAL; STOICHIOMETRY;

CHLOROPHENOLS; DRUG SYNERGISM; ENVIRONMENTAL POLLUTANTS; ESCHERICHIA COLI; HYDROGEN-ION CONCENTRATION; IRON; PHENANTHROLINES;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 33846660441     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/06-306R.1     Document Type: Article

References (47)

1. Cork DJ, Krueger JP. 1991. Microbial transformations of herbicides and pesticides. Adv Appl Microbiol 36:1-66.
2. Domeno C, Munizza G, Nerin C. 2005. Development of a solid-phase microextraction method for direct determination of pentachlorophenol in paper and board samples: Comparison with conventional extraction method. J Chromatogr A 1095:8-15.
3. Mills T, Arnold B, Sivakumaran S, Northcott G, Vogeler I, Robinson B, Norling C, Leonil D. 2006. Phytoremediation and long-term site management of soil contaminated with pentachlorophenol (PCP) and heavy metals. J Environ Manag 79:232-241.
4. Morville S, Scheyer A, Mirabel P, Millet M. 2006. Spatial and geographical variations of urban, suburban and rural atmospheric concentrations of phenols and nitrophenols. Environ Sci Pollut Res Int 13:83-89.
5. Bar-Or Y. 1997. The Intermediate Report of Israel Ministry of Environment. Israel Ministry of the Environment, Jerusalem, Israel, p 121.
6. World Health Organization. 1987. Pentachlorophenol, IPCS Environmental Health Criteria, Vol 71. United Nations Environment Program, International Labor Organization, Geneva, Switzerland.
7. Seiler JP. 1991. Pentachlorophenol. Mutat Res 257:27-47.
8. Kutz FW, Murphy RS, Strassman SC. 1978. Survey of pesticide residues and their metabolites in urine from the general population. In Rao KR, ed, Pentachlorophenol: Chemistry, Pharmacology and Environmental Toxicology. Plenum, New York, NY, USA, pp 363-369.
9. U.S. Agency for Toxic Substance and Disease Registry. 2001. Toxicological profile for pentachlorophenol. Atlanta, GA.
10. Springael D, Diels L, Hooyberghs L, Kreps S, Mergeay M. 1993. Construction and characterization of heavy metal-resistant halo-aromatic- degrading Alcaligenes eutrophus strains. Appl Environ Microbiol 59:334-339.
11. Wall AJ, Stratton GW. 1994. Effects of a chromated-copper-arsenate wood preservative on the bacterial degradation of pentachlorophenol. Can J Microbiol 40:388-392.
12. Lamar RT, Larsen MJ, Kirk TK. 1990. Sensitivity to and degradation of pentachlorophenol by Phanerochaete spp. Appl Environ Microbiol 56:3519-3526.
13. Besser JM, Wang N, Dwyer FJ, Mayer FL Jr, Ingersoll CG. 2005. Assessing contaminant sensitivity of endangered and threatened aquatic species: Part II. Chronic toxicity of copper and pentachlorophenol to two endangered species and two surrogate species. Arch Environ Contam Toxicol 48:155-165.
14. Chevion M. 1988. A site-specific mechanism for free radical induced biological damage: The essential role of redox-active transition metals. Free Radic Biol Med 5:27-37.
15. Chevion M, Jiang Y, Har-El R, Berenshtein E, Uretzky G, Kitrossky N. 1993. Copper and iron are mobilized following myocardial ischemia: Possible predictive criteria for tissue injury. Proc Natl Acad Sci U S A 90:1102-1106.
16. Kawanishi S, Hiraku Y, Murata M, Oikawa S. 2002. The role of metals in site-specific DNA damage with reference to carcinogenesis. Free Radic Biol Med 32:822-832.
17. Moreira PI, Siedlak SL, Aliev G, Zhu X, Cash AD, Smith MA, Perry G. 2005. Oxidative stress mechanisms and potential therapeutics in Alzheimer disease. J Neural Transm 112:921-932.
18. Imlay JA, Linn S. 1988. DNA damage and oxygen radical toxicity. Science 240:1302-1309.
19. Halliwell B, Gutteridge JM. 1990. Role of free radicals and catalytic metal ions in human disease: An overview. Methods Enzymol 186:1-85.
20. Lu H, Shi X, Costa M, Huang C. 2005. Carcinogenic effect of nickel compounds. Mol Cell Biochem 279:45-67.
21. Bagchi D, Joshi SS, Bagchi M, Balmoori J, Benner EJ, Kuszynski CA, Stohs SJ. 2000. Cadmium- and chromium-induced oxidative stress, DNA damage, and apoptotic cell death in cultured human chronic myelogenous leukemic K562 cells, promyelocytic leukemic HL-60 cells, and normal human peripheral blood mononuclear cells. Journal of Biochemical and Molecular Toxicology 14:33-41.
22. Travacio M, Maria Polo J, Llesuy S. 2000. Chromium(VI) induces oxidative stress in the mouse brain. Toxicology 150:137-146.
23. Sugden KD, Stearns DM. 2000. The role of chromium(V) in the mechanism of chromate-induced oxidative DNA damage and cancer. J Environ Pathol Toxicol Oncol 19:215-230.
24. Stohs SJ, Bagchi D, Hassoun E, Bagchi M. 2000. Oxidative mechanisms in the toxicity of chromium and cadmium ions. J Environ Pathol Toxicol Oncol 19:201-213.
25. Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M. 2006. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem-Biol Interact 160:1-40.
26. Voitkun V, Zhitkovich A, Costa M. 1998. Cr(III)-mediated crosslinks of glutathione or amino acids to the DNA phosphate backbone are mutagenic in human cells. Nucleic Acids Res 26:2024-2030.
27. Banks MK, Schwab AP. 2006. Ecotoxicity of pentachlorophenol in contaminated soil as affected by soil type. J Environ Sci Health Part A Toxic-Hazard Subst Environ Eng 41:117-128.
28. van Ommen B, Adang A, Muller F, van Bladeren PJ. 1986. The microsomal metabolism of pentachlorophenol and its covalent binding to protein and DNA. Chem-Biol Interact 60:1-11.
29. Klein CB, Frenkel K, Costa M. 1991. The role of oxidative processes in metal carcinogenesis. Chem Res Toxicol 4:592-604.
30. Costa M. 1991. Molecular mechanisms of nickel carcinogenesis. Annu Rev Pharmacol Toxicol 31:321-337.
31. Liu D, Thomson K, Kaiser KL. 1982. Quantitative structure-toxicity relationship of halogenated phenols on bacteria. Bull Environ Contam Toxicol 29:130-136.
32. Levine RL, Williams JA, Stadtman ER, Shacter E. 1994. Carbonyl assays for determination of oxidatively modified proteins. Methods Enzymol 233:346-357.
33. Witte I, Zhu BZ, Lueken A, Magnani D, Stossberg H, Chevion M. 2000. Protection by desferrioxamine and other hydroxamic acids against tetrachlorohydroquinone-induced cyto- and genotoxicity in human fibroblasts. Free Radic Biol Med 28:693-700.
34. Chevion M, Zhu BZ, Schechtman S. 2002. Synergistic biocidal activity if ternary complexes of negatively-charged biocides (component A), transition metal ions (component B), and neutral chelators (component C). Patent 6,426,093. U.S. Patent Office, Washington, DC.
35. Albert A. 1985. Selective Toxicity : The Physico-Chemical Basis of Therapy. Chapman and Hall, New York, NY, USA.
36. Weinbach EC, Garbus J. 1969. Mechanism of action of reagents that uncouple oxidative phosphorylation. Nature 221:1016-1018.
37. Alluvia S, Zhang A, Argaman L, Tiwari A, Storz G. 1998. The Escherichia coli OxyS regulatory RNA represses fhlA translation by blocking ribosome binding. EMBO J 17:6069-6075.
38. Altuvia S, Weinstein-Fischer D, Zhang A, Postow L, Storz G. 1997. A small, stable RNA induced by oxidative stress: Role as a pleiotropic regulator and antimutator. Cell 90:43-53.
39. Zheng M, Aslund F, Storz G. 1998. Activation of the OxyR transcription factor by reversible disulfide bond formation. Science 279:1718-1721.
40. Amici A, Levine RL, Tsai L, Stadtman ER. 1989. Conversion of amino acid residues in proteins and amino acid homopolymers to carbonyl derivatives by metal-catalyzed oxidation reactions. J Biol Chem 264:3341-3346.
41. Kontoghiorghes GJ, Piga A, Hoffbrand AV. 1986. Cytotoxic and DNA-inhibitory effects of iron chelators on human leukaemic cell lines. Hematol Oncol 4:195-204.
42. Balla G, Vercellotti GM, Eaton JW, Jacob HS. 1990. Iron loading of endothelial cells augments oxidant damage. J Lab Clin Med 116:546-554.
43. Luo Y, Han Z, Chin SM, Linn S. 1994. Three chemically distinct types of oxidants formed by iron-mediated Fenton reactions in the presence of DNA. Proc Natl Acad Sci U S A 91:12438-12442.
44. de Avellar IG, Magalhaes MM, Silva AB, Souza LL, Leitao AC, Hermes-Lima M. 2004. Reevaluating the role of 1,10-phenanthroline in oxidative reactions involving ferrous ions and DNA damage. Biochim Biophys Acta 1675:46-53.
45. Furtado FA, Asad NR, Leitao AC. 1997. Effects of 1,10-phenanthroline and hydrogen peroxide in Escherichia coli: Lethal interaction. Mutat Res 385:251-258.
46. Tjalve H, Gottofrey J. 1991. Effects of lipophilic complex formation on the uptake and distribution of some metals in fish. Pharmacol Toxicol 68:430-439.
47. Mohindru A, Fisher JM, Rabinovitz M. 1983. Bathocuproine sulphonate: A tissue culture-compatible indicator of copper-mediated toxicity. Nature 303:64-65.