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
Hauptverfasser: Reissbrodt, R, Ramiandrasoa, F, Bricard, L, Kunesch, G
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container_title Biometals
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creator Reissbrodt, R
Ramiandrasoa, F
Bricard, L
Kunesch, G
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.
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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. 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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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