{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T20:43:15Z","timestamp":1760820195029,"version":"3.32.0"},"reference-count":44,"publisher":"Oxford University Press (OUP)","issue":"3","license":[{"start":{"date-parts":[[1995,3,1]],"date-time":"1995-03-01T00:00:00Z","timestamp":794016000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/pages\/standard-publication-reuse-rights"},{"start":{"date-parts":[[2009,10,26]],"date-time":"2009-10-26T00:00:00Z","timestamp":1256515200000},"content-version":"vor","delay-in-days":5353,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Junta Nacional de Investiga\u00e7ao Cientifica e Tecnol%oAgica","award":["PBICT\/C\/CEN\/1014\/92","BM\/3493\/92-RM"],"award-info":[{"award-number":["PBICT\/C\/CEN\/1014\/92","BM\/3493\/92-RM"]}]}],"content-domain":{"domain":["setac.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[1995,3,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Pseudomonas syringae cells were exposed to 100 \u03bcM copper alone, or to previously equilibrated copper sulfate-ligand solutions. Ligand concentrations were determined experimentally as those that reduced the free copper concentration to 5 \u03bcM (determined with a Cu2+-selective electrode). These values were in agreement with those calculated by computational equilibrium simulation based on published stability constants. Exposure of P. syringae cells to copper sulfate, chloride, or nitrate resulted in similar high mortality, suggesting that copper was responsible for cell death. Acetate, succinate, proline, lysine, cysteine, and EDTA significantly reduced both the amount of copper bound to the cells and cell death, indicating that not only strong chelating agents but also weak and moderate copper ligands can effectively antagonize copper toxicity. However, cysteine and EDTA were considerably more effective than acetate, succinate, proline, and lysine, indicating that copper toxicity is not simply a function of free copper concentration but depends on the nature of the ligand. The results suggested that a significant fraction of copper bound to acetate, succinate, proline, or lysine was displaced to the bacteria or, alternatively, mixed copper-ligand-cell complexes could be formed. On the contrary, none of these phenomena occurred for the copper complexes with cysteine or EDTA.<\/jats:p>","DOI":"10.1002\/etc.5620140303","type":"journal-article","created":{"date-parts":[[2010,3,17]],"date-time":"2010-03-17T01:56:46Z","timestamp":1268791006000},"page":"369-373","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":36,"title":["Organic ligands reduce copper toxicity in <i>Pseudomonas syringae<\/i>"],"prefix":"10.1093","volume":"14","author":[{"given":"Manuel","family":"Azenha","sequence":"first","affiliation":[{"name":"Departamento de Quimica, Faculdade de Ci\u00eancias do Porto, 4000 Porto, Portugal"}]},{"given":"M. Teresa","family":"Vasconcelos","sequence":"additional","affiliation":[{"name":"Departamento de Quimica, Faculdade de Ci\u00eancias do Porto, 4000 Porto, Portugal"}]},{"given":"Jo\u00e3o P. S.","family":"Cabral","sequence":"additional","affiliation":[]}],"member":"286","published-online":{"date-parts":[[1995,3,1]]},"reference":[{"volume-title":"Metals and Microorganisms","year":"1989","author":"Hughes","key":"2025010615051428700_bib1"},{"key":"2025010615051428700_bib2","first-page":"178","volume-title":"Microbiology of Extreme Environments","author":"Gadd","year":"1990"},{"key":"2025010615051428700_bib3","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/0005-2744(81)90127-3","article-title":"Purification and some properties of the soluble hydrogenase from Chromatium vinosum","volume":"657","author":"van Heerikhuizen","year":"1981","journal-title":"Biochim. Biophys. Acta"},{"key":"2025010615051428700_bib4","doi-asserted-by":"crossref","first-page":"7045","DOI":"10.1016\/S0021-9258(17)39835-6","article-title":"The physical and catalytic properties of hydrogenase II of Clostridium pasteurianum","volume":"259","author":"Adams","year":"1984","journal-title":"J. Biol. Chem."},{"key":"2025010615051428700_bib5","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1111\/j.1432-1033.1985.tb09279.x","article-title":"Copper ions as inhibitors of protein C of soluble methane monooxygenase of Methylococcus capsulatus (Bath)","volume":"153","author":"Green","year":"1985","journal-title":"Eur. J. Biochem."},{"key":"2025010615051428700_bib6","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1111\/j.1432-1033.1986.tb09577.x","article-title":"Purification and properties of membrane-bound hydrogenase isoenzyme I from anaerobically grown Escherichia coli K 12","volume":"156","author":"Sawers","year":"1986","journal-title":"Eur. J. Biochem."},{"key":"2025010615051428700_bib7","doi-asserted-by":"crossref","first-page":"1689","DOI":"10.1128\/aem.54.7.1689-1693.1988","article-title":"Effects of glucose concentrations on cadmium, copper, mercury, and zinc toxicity to a Klebsiella sp","volume":"54","author":"Brynhildsen","year":"1988","journal-title":"Appl. Environ. Microbiol."},{"key":"2025010615051428700_bib8","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1128\/aem.55.1.43-49.1989","article-title":"Acute copper and cupric ion toxicity in an estuarine microbiol community","volume":"55","author":"Jonas","year":"1989","journal-title":"Appl. Environ. Microbiol."},{"key":"2025010615051428700_bib9","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1139\/m85-016","article-title":"The toxicity of copper to the marine bacterium Vibrio alginolyticus","volume":"31","author":"Schreiber","year":"1985","journal-title":"Can. J. Microbiol."},{"key":"2025010615051428700_bib10","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1111\/j.1574-6968.1991.tb04546.x","article-title":"The antibacterial action of cupric ions in Pseudomonas syringae","volume":"79","author":"Cabral","year":"1991","journal-title":"FEMS Microbiol. Lett."},{"key":"2025010615051428700_bib11","first-page":"141","article-title":"Induction of potassium efflux by cupric ions in Pseudomonas syringae ATCC 12271 and its correlation with cell viability","volume":"60","author":"Cabral","year":"1989","journal-title":"Microbios"},{"key":"2025010615051428700_bib12","doi-asserted-by":"crossref","first-page":"2481","DOI":"10.1099\/00221287-136-12-2481","article-title":"Plasmolysis induced by very low concentrations of Cu2+ in Pseudomonas syringae ATCC 12271, and its relation with cation fluxes","volume":"136","author":"Cabral","year":"1990","journal-title":"J. Gen. Microbiol."},{"key":"2025010615051428700_bib13","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1128\/jb.63.2.279-290.1952","article-title":"The effect of metallic ions on the growth and morphology of Clostridium perfringens","volume":"63","author":"Shankar","year":"1952","journal-title":"J. Bacteriol."},{"key":"2025010615051428700_bib14","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1128\/jb.65.2.157-159.1953","article-title":"Growth inhibitory action of copper for Mycobacterium phlei","volume":"65","author":"Pratt","year":"1953","journal-title":"J. Bacteriol."},{"key":"2025010615051428700_bib15","first-page":"7","article-title":"Chromium and copper sensitivity and tolerance of Klebsiella (Aerobacter) aerogenes","volume":"4","author":"Baldry","year":"1977","journal-title":"Microbios Lett."},{"key":"2025010615051428700_bib16","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1017\/S002531540002467X","article-title":"Seawater, the natural medium of phytoplankton: II. Trace metals and chelation, and general discussion","volume":"44","author":"Johnston","year":"1964","journal-title":"J. Mar. Biol. Assoc. UK"},{"key":"2025010615051428700_bib17","doi-asserted-by":"crossref","first-page":"993","DOI":"10.4319\/lo.1973.18.6.0993","article-title":"A biological measurement of the copper complexation capacity of seawater","volume":"18","author":"Davey","year":"1973","journal-title":"Limnol. Oceanogr."},{"key":"2025010615051428700_bib18","first-page":"511","article-title":"The relationship between cupric ion activity and the toxicity of copper to phytoplankton","volume":"34","author":"Sunda","year":"1976","journal-title":"J. Mar. Res."},{"key":"2025010615051428700_bib19","doi-asserted-by":"crossref","first-page":"283","DOI":"10.4319\/lo.1978.23.2.0283","article-title":"Copper sensitivity of Gonyaulax tamarensis","volume":"23","author":"Anderson","year":"1978","journal-title":"Limnol. Oceanogr."},{"key":"2025010615051428700_bib20","first-page":"761","article-title":"The response of a marine bacterium to cupric ion and its use to estimate ion activity in seawater","volume":"37","author":"Sunda","year":"1979","journal-title":"J. Mar. Res."},{"key":"2025010615051428700_bib21","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1017\/S0025315400024280","article-title":"Toxicity of heavy metals to the marine diatom Ditylum grightwelln (West) Grunow Correlation between toxicity and metal speciation","volume":"60","author":"Canterford","year":"1980","journal-title":"J Mar Biol Assoc UK"},{"key":"2025010615051428700_bib22","doi-asserted-by":"crossref","first-page":"1258","DOI":"10.1094\/Phyto-81-1258","article-title":"Relationship of free ionic copper and toxicity to bacteria in solutions of organic com pounds","volume":"81","author":"Menkissoglu","year":"1991","journal-title":"Phytopathology"},{"volume-title":"Toxic Metal Chemistry in Marine Environment","year":"1992","author":"Sadiq","key":"2025010615051428700_bib23"},{"key":"2025010615051428700_bib24","first-page":"600","article-title":"Effect of copper on the growth of","volume":"50","author":"Lee","year":"1993","journal-title":"Anacystis nidulans Bull Environ Con tam Toxicol"},{"volume-title":"Guide to Plant Pathogenic Bacteria","year":"1986","author":"Bradbury","key":"2025010615051428700_bib25"},{"key":"2025010615051428700_bib26","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1094\/PD-67-639","article-title":"Effectiveness of selected chemicals in inhibiting Pseudomonas syringae pv tomato in vitro and in controlling bacterial speck.","volume":"67","author":"Colin","year":"1983","journal-title":"Plant Dis"},{"key":"2025010615051428700_bib27","first-page":"69","volume-title":"Phytobacteriology and Plant Bacterial Diseases of Quarantine Significance Proceedings","author":"Tamietti","year":"1984"},{"key":"2025010615051428700_bib28","doi-asserted-by":"crossref","first-page":"1048","DOI":"10.1094\/PD-70-1048","article-title":"Comparison of biological and chemical treatments for control of bacterial speck of tomato under field conditions of Morocco","volume":"70","author":"Colin","year":"1986","journal-title":"Plant Dis"},{"key":"2025010615051428700_bib29","first-page":"55","volume-title":"Ecology of Leaf Surface Micro organisms","author":"Baker","year":"1971"},{"key":"2025010615051428700_bib30","first-page":"39","volume-title":"Ecology of Leaf Surface Micro organisms","author":"Holloway","year":"1971"},{"key":"2025010615051428700_bib31","first-page":"67","volume-title":"Ecology of Leaf Surface Micro-organisms","author":"Tukey","year":"1971"},{"key":"2025010615051428700_bib32","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1007\/978-3-642-68234-6_10","volume-title":"Plant Carbohydrates II Extracellular Carbohydrates Encyclopedia of Plant Physiology","author":"Kolattukudy","year":"1981"},{"volume-title":"Stability Constants of Metal-Ion Complexes","year":"1964","author":"Sillen","key":"2025010615051428700_bib33"},{"volume-title":"Stability Constants of Metal-Ion Complexes","year":"1971","author":"Sillen","key":"2025010615051428700_bib34"},{"key":"2025010615051428700_bib35","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1021\/bi00866a011","article-title":"Hydrogen ion buffers for biological research","volume":"5","author":"Good","year":"1966","journal-title":"Biochemistry"},{"volume-title":"Critical Stability Constants","year":"1974","author":"Martell","key":"2025010615051428700_bib36"},{"volume-title":"Critical Stability Constants","year":"1977","author":"Martell","key":"2025010615051428700_bib37"},{"key":"2025010615051428700_bib38","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/0039-9140(76)80039-2","article-title":"Calculation of all equilibrium concentrations in a system of competing complexation","volume":"23","author":"Ginzburg","year":"1976","journal-title":"Talanta"},{"key":"2025010615051428700_bib39","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1139\/m92-019","article-title":"Mode of antibacterial action of dodine (dodecylguanidine monoacetate) in Pseudomonas syringae","volume":"38","author":"Cabral","year":"1992","journal-title":"Can J Microbiol"},{"key":"2025010615051428700_bib40","first-page":"1","volume-title":"Methods in Microbiology","author":"Herbert","year":"1990"},{"key":"2025010615051428700_bib41","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/S0065-3233(08)60424-6","article-title":"Complex formation between metallic cations and proteins, peptides, and amino acids","volume":"11","author":"Gurd","year":"1956","journal-title":"Adv Protein Chem"},{"key":"2025010615051428700_bib42","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/S0065-3233(08)60043-1","article-title":"Crystal structures of metal-peptide complexes","volume":"22","author":"Freeman","year":"1967","journal-title":"Adv Protein Chem"},{"key":"2025010615051428700_bib43","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1016\/S0010-8545(00)82028-7","article-title":"Models for copper-protein interaction based on solution and crystal structure studies","volume":"12","author":"Osterberg","year":"1974","journal-title":"Coordination Chemistry Review"},{"key":"2025010615051428700_bib44","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-642-81148-7","volume-title":"Transition Metals in Biochemistry","author":"Brill","year":"1977"}],"container-title":["Environmental Toxicology and Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fetc.5620140303","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/academic.oup.com\/etc\/article-pdf\/14\/3\/369\/60598706\/5620140303.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/etc\/article-pdf\/14\/3\/369\/60598706\/5620140303.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,6]],"date-time":"2025-01-06T15:18:41Z","timestamp":1736176721000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/etc\/article\/14\/3\/369\/7862224"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1995,3,1]]},"references-count":44,"journal-issue":{"issue":"3","published-online":{"date-parts":[[1995,3,1]]},"published-print":{"date-parts":[[1995,3,1]]}},"URL":"https:\/\/doi.org\/10.1002\/etc.5620140303","relation":{},"ISSN":["0730-7268","1552-8618"],"issn-type":[{"type":"print","value":"0730-7268"},{"type":"electronic","value":"1552-8618"}],"subject":[],"published-other":{"date-parts":[[1995,3,1]]},"published":{"date-parts":[[1995,3,1]]},"assertion":[{"value":"1994-03-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"1994-07-12","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2009-10-26","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}