Siderophore activity of chemically synthesized dihydroxybenzoyl derivatives of spermidines and cystamide
Chemically synthesized dihydroxybenzoyl derivatives of spermidine and cystamide containing two-, three- and four-bidentates with the hydroxyl groups in 2,3 or 3,4 position were examined in cross-feeding tests using Gram-negative siderophore indicator strains carrying different iron-related markers,...
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Veröffentlicht in: | Biometals 1997-04, Vol.10 (2), p.95-103 |
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description | Chemically synthesized dihydroxybenzoyl derivatives of spermidine and cystamide containing two-, three- and four-bidentates with the hydroxyl groups in 2,3 or 3,4 position were examined in cross-feeding tests using Gram-negative siderophore indicator strains carrying different iron-related markers, and two Mycobacterium spp. The catecholates were unable to feed tonB mutants of E. coli and S. typhimurium as well as the fepA, fiu, cir mutant of E. coli, pointing to a tonB- and fepA, cir, fiu-dependent transport. Bis(2,3-dihydroxybenzoyl)derivatives promoted Salmonella spp, E. coli, K. pneumoniae and P. aeruginosa strains significantly better than did 3,4-dihydroxybenzoyl derivatives. N4-substituted spermidines acted more effectively than non-substituted derivatives. Bis(2,3-dihydroxybenzoyl) cystamide was superior to the other catecholates tested in growth promotion of Gram-negative bacteria. The two four-bidentates and the tri-bidentate reacted to K. pneumoniae in an inhibitory mode. The position of the hydroxyl groups did not significantly influence the growth promotion of M. smegmatis and M. fortiutum in the cases of substituted spermidines and of cystamides. |
doi_str_mv | 10.1023/A:1018327122629 |
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Bis(2,3-dihydroxybenzoyl)derivatives promoted Salmonella spp, E. coli, K. pneumoniae and P. aeruginosa strains significantly better than did 3,4-dihydroxybenzoyl derivatives. N4-substituted spermidines acted more effectively than non-substituted derivatives. Bis(2,3-dihydroxybenzoyl) cystamide was superior to the other catecholates tested in growth promotion of Gram-negative bacteria. The two four-bidentates and the tri-bidentate reacted to K. pneumoniae in an inhibitory mode. The position of the hydroxyl groups did not significantly influence the growth promotion of M. smegmatis and M. fortiutum in the cases of substituted spermidines and of cystamides.</description><identifier>ISSN: 0966-0844</identifier><identifier>EISSN: 1572-8773</identifier><identifier>DOI: 10.1023/A:1018327122629</identifier><identifier>PMID: 9210292</identifier><language>eng</language><publisher>Netherlands: Springer Nature B.V</publisher><subject><![CDATA[Amides - chemistry ; Bacteria ; Bacteriology ; Benzene Derivatives - chemistry ; Derivatives ; E coli ; Escherichia coli ; Escherichia coli - drug effects ; Escherichia coli - genetics ; Escherichia coli - growth & development ; Escherichia coli - metabolism ; Iron Chelating Agents - chemistry ; Iron Chelating Agents - toxicity ; Klebsiella pneumoniae ; Klebsiella pneumoniae - drug effects ; Klebsiella pneumoniae - genetics ; Klebsiella pneumoniae - growth & development ; Klebsiella pneumoniae - metabolism ; Magnetic Resonance Spectroscopy ; Mutation - drug effects ; Mutation - genetics ; Mycobacterium ; Mycobacterium - drug effects ; Mycobacterium - genetics ; Mycobacterium - growth & development ; Mycobacterium - metabolism ; Oxidation-Reduction ; Pseudomonas aeruginosa ; Pseudomonas aeruginosa - drug effects ; Pseudomonas aeruginosa - genetics ; Pseudomonas aeruginosa - growth & development ; Pseudomonas aeruginosa - metabolism ; Salmonella typhimurium ; Salmonella typhimurium - drug effects ; Salmonella typhimurium - genetics ; Salmonella typhimurium - growth & development ; Salmonella typhimurium - metabolism ; Siderophores - chemistry ; Siderophores - toxicity ; Spermidine - analogs & derivatives ; Spermidine - chemistry ; Structure-Activity Relationship]]></subject><ispartof>Biometals, 1997-04, Vol.10 (2), p.95-103</ispartof><rights>Chapman and Hall 1997</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c311t-5ea325721933c45a8d7ac186531a13033ffd74d981b911b3fd6ee4299982bbf93</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9210292$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Reissbrodt, R</creatorcontrib><creatorcontrib>Ramiandrasoa, F</creatorcontrib><creatorcontrib>Bricard, L</creatorcontrib><creatorcontrib>Kunesch, G</creatorcontrib><title>Siderophore activity of chemically synthesized dihydroxybenzoyl derivatives of spermidines and cystamide</title><title>Biometals</title><addtitle>Biometals</addtitle><description>Chemically synthesized dihydroxybenzoyl derivatives of spermidine and cystamide containing two-, three- and four-bidentates with the hydroxyl groups in 2,3 or 3,4 position were examined in cross-feeding tests using Gram-negative siderophore indicator strains carrying different iron-related markers, and two Mycobacterium spp. The catecholates were unable to feed tonB mutants of E. coli and S. typhimurium as well as the fepA, fiu, cir mutant of E. coli, pointing to a tonB- and fepA, cir, fiu-dependent transport. Bis(2,3-dihydroxybenzoyl)derivatives promoted Salmonella spp, E. coli, K. pneumoniae and P. aeruginosa strains significantly better than did 3,4-dihydroxybenzoyl derivatives. N4-substituted spermidines acted more effectively than non-substituted derivatives. Bis(2,3-dihydroxybenzoyl) cystamide was superior to the other catecholates tested in growth promotion of Gram-negative bacteria. The two four-bidentates and the tri-bidentate reacted to K. pneumoniae in an inhibitory mode. The position of the hydroxyl groups did not significantly influence the growth promotion of M. smegmatis and M. fortiutum in the cases of substituted spermidines and of cystamides.</description><subject>Amides - chemistry</subject><subject>Bacteria</subject><subject>Bacteriology</subject><subject>Benzene Derivatives - chemistry</subject><subject>Derivatives</subject><subject>E coli</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - genetics</subject><subject>Escherichia coli - growth & development</subject><subject>Escherichia coli - metabolism</subject><subject>Iron Chelating Agents - chemistry</subject><subject>Iron Chelating Agents - toxicity</subject><subject>Klebsiella pneumoniae</subject><subject>Klebsiella pneumoniae - drug effects</subject><subject>Klebsiella pneumoniae - genetics</subject><subject>Klebsiella pneumoniae - growth & development</subject><subject>Klebsiella pneumoniae - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mutation - drug effects</subject><subject>Mutation - genetics</subject><subject>Mycobacterium</subject><subject>Mycobacterium - drug effects</subject><subject>Mycobacterium - genetics</subject><subject>Mycobacterium - growth & development</subject><subject>Mycobacterium - metabolism</subject><subject>Oxidation-Reduction</subject><subject>Pseudomonas aeruginosa</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Pseudomonas aeruginosa - genetics</subject><subject>Pseudomonas aeruginosa - growth & development</subject><subject>Pseudomonas aeruginosa - metabolism</subject><subject>Salmonella typhimurium</subject><subject>Salmonella typhimurium - drug effects</subject><subject>Salmonella typhimurium - genetics</subject><subject>Salmonella typhimurium - growth & development</subject><subject>Salmonella typhimurium - metabolism</subject><subject>Siderophores - chemistry</subject><subject>Siderophores - toxicity</subject><subject>Spermidine - analogs & derivatives</subject><subject>Spermidine - chemistry</subject><subject>Structure-Activity 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activity of chemically synthesized dihydroxybenzoyl derivatives of spermidines and cystamide</title><author>Reissbrodt, R ; Ramiandrasoa, F ; Bricard, L ; Kunesch, G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c311t-5ea325721933c45a8d7ac186531a13033ffd74d981b911b3fd6ee4299982bbf93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Amides - chemistry</topic><topic>Bacteria</topic><topic>Bacteriology</topic><topic>Benzene Derivatives - chemistry</topic><topic>Derivatives</topic><topic>E coli</topic><topic>Escherichia coli</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - genetics</topic><topic>Escherichia coli - growth & development</topic><topic>Escherichia coli - metabolism</topic><topic>Iron Chelating Agents - chemistry</topic><topic>Iron Chelating Agents - toxicity</topic><topic>Klebsiella pneumoniae</topic><topic>Klebsiella pneumoniae - 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Edition</collection><collection>Engineering Collection</collection><collection>Environmental Science Collection</collection><collection>ProQuest Central Basic</collection><jtitle>Biometals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reissbrodt, R</au><au>Ramiandrasoa, F</au><au>Bricard, L</au><au>Kunesch, G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Siderophore activity of chemically synthesized dihydroxybenzoyl derivatives of spermidines and cystamide</atitle><jtitle>Biometals</jtitle><addtitle>Biometals</addtitle><date>1997-04-01</date><risdate>1997</risdate><volume>10</volume><issue>2</issue><spage>95</spage><epage>103</epage><pages>95-103</pages><issn>0966-0844</issn><eissn>1572-8773</eissn><abstract>Chemically synthesized dihydroxybenzoyl derivatives of spermidine and cystamide containing two-, three- and four-bidentates with the hydroxyl groups in 2,3 or 3,4 position were examined in cross-feeding tests using Gram-negative siderophore indicator strains carrying different iron-related markers, and two Mycobacterium spp. The catecholates were unable to feed tonB mutants of E. coli and S. typhimurium as well as the fepA, fiu, cir mutant of E. coli, pointing to a tonB- and fepA, cir, fiu-dependent transport. Bis(2,3-dihydroxybenzoyl)derivatives promoted Salmonella spp, E. coli, K. pneumoniae and P. aeruginosa strains significantly better than did 3,4-dihydroxybenzoyl derivatives. N4-substituted spermidines acted more effectively than non-substituted derivatives. Bis(2,3-dihydroxybenzoyl) cystamide was superior to the other catecholates tested in growth promotion of Gram-negative bacteria. The two four-bidentates and the tri-bidentate reacted to K. pneumoniae in an inhibitory mode. The position of the hydroxyl groups did not significantly influence the growth promotion of M. smegmatis and M. fortiutum in the cases of substituted spermidines and of cystamides.</abstract><cop>Netherlands</cop><pub>Springer Nature B.V</pub><pmid>9210292</pmid><doi>10.1023/A:1018327122629</doi><tpages>9</tpages></addata></record> |
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subjects | Amides - chemistry Bacteria Bacteriology Benzene Derivatives - chemistry Derivatives E coli Escherichia coli Escherichia coli - drug effects Escherichia coli - genetics Escherichia coli - growth & development Escherichia coli - metabolism Iron Chelating Agents - chemistry Iron Chelating Agents - toxicity Klebsiella pneumoniae Klebsiella pneumoniae - drug effects Klebsiella pneumoniae - genetics Klebsiella pneumoniae - growth & development Klebsiella pneumoniae - metabolism Magnetic Resonance Spectroscopy Mutation - drug effects Mutation - genetics Mycobacterium Mycobacterium - drug effects Mycobacterium - genetics Mycobacterium - growth & development Mycobacterium - metabolism Oxidation-Reduction Pseudomonas aeruginosa Pseudomonas aeruginosa - drug effects Pseudomonas aeruginosa - genetics Pseudomonas aeruginosa - growth & development Pseudomonas aeruginosa - metabolism Salmonella typhimurium Salmonella typhimurium - drug effects Salmonella typhimurium - genetics Salmonella typhimurium - growth & development Salmonella typhimurium - metabolism Siderophores - chemistry Siderophores - toxicity Spermidine - analogs & derivatives Spermidine - chemistry Structure-Activity Relationship |
title | Siderophore activity of chemically synthesized dihydroxybenzoyl derivatives of spermidines and cystamide |
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