Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response

Williams, Jade; Sheldon, Jessica R.; Imlay, Hunter; Dutter, Brendan F.; Draelos, Matthew M; Skaar, Eric P.; Sulikowski, Gary A.

doi:10.1021/acs.orglett.8b03857

Cited by 13 publications

(13 citation statements)

References 35 publications

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“…To this end, a known Chrome Azurol S (CAS) Fe(III) binding assay was performed . The CAS assay has been used to assess the iron‐binding ability of coelichelin, hinduchelins, and bisucaberin . Briefly, a solution of Fe(III)‐CAS complex with an absorbance at 630 nm (Abs630) was treated with a dilution series of siderophores (1.560 to 200 µ m ).…”

Section: Resultsmentioning

confidence: 99%

“…The high binding affinity is attributable to the dual stabilizing effects of the presence of multiple bidentate ligands embedded into a single molecular scaffold. Among hundreds of natural siderophores, several ligand classes have been identified, namely hydroxamates, catecholates, and α ‐hydroxyl carboxylates , . Other less prevalent ligand classes also exist, such as phenolates and diazeniumdiolates …”

Section: Introductionmentioning

confidence: 99%

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Convergent Synthesis of Macrocyclic and Linear Desferrioxamines

et al. 2020

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Polyhydroxamate desferrioxamines (DFO) are nontoxic siderophores endowed with high potential for development of therapeutic chelating agents. Herein, we report a modular and convergent strategy for diverse synthesis of macrocyclic and linear DFOs. The strategy employed orthogonally protected N‐hydroxy‐N‐succinylcadaverine building blocks, which allowed bidirectional extension of the DFO structure. The efficiency of the new strategy was demonstrated by the total synthesis of 44‐membered macrocyclic DFO‐T1, as well as four related DFO compounds in 11–13 linear steps and 2.1 %–10 % overall yields. Comparison of the iron binding affinity of the DFOs revealed DFO‐E as the best chelator.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Convergent Synthesis of Macrocyclic and Linear Desferrioxamines

et al. 2020

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“…Miharamycin was a peptidyl nucleoside antibiotic, showing a remarkable activity against the rice blast disease (Kang et al, 2019). As a ferric-iron-chelating peptide, coelichelin effectively harnessed the microbe's own cellular machinery to improve cellular uptake and delivery of the antimicrobial compounds (Williams et al, 2019). Nigericin showed strong antibacterial and anticancer activities by moving sodium and potassium ions, resulting in changes in the ion gradient in the energetic metabolism (Ortega et al, 2019).…”

Section: Discussionmentioning

confidence: 99%

Anti-Foc RT4 Activity of a Newly Isolated Streptomyces sp. 5–10 From a Medicinal Plant (Curculigo capitulata)

et al. 2021

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Fusarium wilt of banana caused by Fusarium oxysporum f. sp. cubense (Foc) is a disastrous soil-borne fungal disease. Foc tropical race 4 (Foc TR4) can infect almost all banana cultivars. Until now, there is a shortage of safety and effective control methods and commercial banana cultivars with a resistance against Foc TR4. Biocontrol using environmentally friendly microbes is a promising strategy for the management of Foc TR4. Here, a strain 5–10, newly isolated from a medicinal plant (Curculigo capitulata), exhibited a high antifungal activity against Foc TR4. Combing the morphological characteristics and molecular identification, strain 5–10 was classified as a Streptomyces genus. The sequenced genome revealed that more than 39 gene clusters were involved in the biosynthesis of secondary metabolites. Some multidrug resistance gene clusters were also identified such as mdtD, vatB, and vgaE. To improve the anti-Foc TR4 activity of the strain 5–10 extracts, an optimization method of fermentation broth was established. Antifungal activity increased by 72.13% under the fermentation system containing 2.86 g/L of NaCl and 11.57% of inoculation amount. After being treated with the strain 5–10 extracts, the Foc TR4 hyphae shrinked, deformed, and ruptured. The membrane integrity and cell ultrastructure incurred irreversible damage. Streptomyces sp. 5–10 extracts play a fungicidal role in Foc TR4. Hence, Streptomyces sp. 5–10 will be a potential biocontrol agent to manage fungal diseases by exploring the microbial fertilizer.

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“…MA37 [6] and Streptomyces strain GP 38 [7], is a potent free radical scavenging agent to protect cell damage caused by the free radicals and exhibited a strong inhibitory effect on the free radical induced lipid peroxidation in a rat brain homogenate. Coelichelin, a ferric-iron chelating peptide, is produced by Streptomyces coelicolor [8]. Germicidin A and B, isolated from S.…”

Section: Full-textmentioning

confidence: 99%

Streptomyces barringtoniae sp. nov., isolated from rhizosphere of plant with antioxidative potential

Wai

Luechapudiporn

Tedsree

et al. 2022

International Journal of Systematic and Evolutionary Microbiology

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A novel actinomycete strain, JA03T, belonging to the genus Streptomyces , was isolated from the rhizosphere of Barringtonia racemosa (L.) Spreng. It was characterized taxonomically using a polyphasic approach. It grew at 25–37 °C, at pH 5–10 and with 6 % (w/v) NaCl. It contained ll-diaminopimelic acid in the cell-wall peptidoglycan. Ribose and glucose were detected in its whole-cell hydrolysate. The predominant cellular fatty acids were iso-C16 : 0, anteiso-C15 : 0, C16 : 0, iso-C14 : 0 and iso-C15 : 0. Detected polar lipids were phosphatidylethanolamine, diphosphatidylglycerol, phosphatidylglycerol, phosphatidylinositol, phosphatidylinositol mannosides, unidentified phospholipids and unidentified amino lipids. Based on the results of 16S rRNA gene sequence analyses, strain JA03T showed highest similarity to Streptomyces filipinensis NBRC 12860T (98.76 %), Streptomyces fodineus TW1S1T (98.69 %) and Streptomyces shenzhennensis 172115T (98.68 %). Strain JA03T has a genome size of 9 092 851 bp with DNA G+C content of 71.28 mol%. The average nucleotide identity (ANI)-blast and ANI-MUMmer values of strain JA03T and related type strains were 79.6–89.2 and 86.7–92.5 %, respectively, and the digital DNA–DNA hybridization values were 27.3–46.4 %. Ethyl acetate extract of JA03T exhibited total phenolic content (33.4±0.6 µg mg−1 gallic acid equivalent), ferric reducing power value (70.8±1.8 µg mg−1 ascorbic acid equivalent) and 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity (IC50=67.0±21.1 µg ml−1). Intracellular reactive oxygen species and NO production in RAW264.7 macrophage cells induced by H2O2 and lipopolysaccharide were inhibited with IC50 of 67.40 and 16.95 µg ml−1, respectively. Based on the taxonomic results, it has been concluded that strain JA03T represents a novel species of the genus Streptomyces for which the name Streptomyces barringtoniae sp. nov., is proposed. The type strain is JA03T (=LMG 32415T=TISTR 2999T).

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Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response

Cited by 13 publications

References 35 publications

Convergent Synthesis of Macrocyclic and Linear Desferrioxamines

Convergent Synthesis of Macrocyclic and Linear Desferrioxamines

Anti-Foc RT4 Activity of a Newly Isolated Streptomyces sp. 5–10 From a Medicinal Plant (Curculigo capitulata)

Streptomyces barringtoniae sp. nov., isolated from rhizosphere of plant with antioxidative potential

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