Antifungal thiopeptide cyclothiazomycin B1 exhibits growth inhibition accompanying morphological changes via binding to fungal cell wall chitin

Mizuhara, Naoko; Kuroda, Manabu; Ogita, Akira; Tanaka, Toshio; Usuki, Yoshinosuke; Fujita, Ken‐ichi

doi:10.1016/j.bmc.2011.08.010

Cited by 50 publications

(42 citation statements)

References 40 publications

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“…78 Furthermore, some of them also exhibit antifungal activity by binding to chitin of the cell walls of fungi. 79 Additionally, polyelectrolytes were found to be nonhemolytic irrespective of the DQth, presenting HC 50 values close to 1000 μg/mL at low DQth and above 5000 μg/mL at higher DQth, thus maintaining excellent selectivity index defined as HC 50 / MIC. In fact, some of them present selectivity values ranging from 600 to 2000.…”

Section: Resultsmentioning

confidence: 99%

High Efficiency Antimicrobial Thiazolium and Triazolium Side-Chain Polymethacrylates Obtained by Controlled Alkylation of the Corresponding Azole Derivatives

et al. 2015

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Two series of antimicrobial polymethacrylates (PMTAs) bearing mono and bis-cationic quaternary ammonium cations (QUATs) were prepared by controlled N-alkylation of 1,3-thiazole and 1,2,3-triazole pendant groups with butyl iodide (PMTAs-BuI). The degree of quaternization (DQ) of the azole heterocycles was monitored by (1)H NMR spectroscopy over a wide range of reaction times. Spectra analysis of the (1)H NMR aromatic region allowed to characterize and quantify the different species involved and, therefore, to control the chemical composition distribution of the amphiphilic polycations. The polymer charge density and the hydrodynamic sizes were measured by zeta potential and dynamic light scattering (DLS), respectively. Consequently, the relationship between structure and antibacterial properties and toxicity was studied. Interestingly, these polyelectrolytes present excellent selective toxicity against bacteria being nonhemolytic even at low values of DQ. Furthermore, they were also evaluated for their microbial time-killing efficiency, presenting a 3 log-reduction in only 15 min. Additionally, the bacteria cell morphology treated with PMTAs-BuI was analyzed.

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Section: Resultsmentioning

confidence: 99%

High Efficiency Antimicrobial Thiazolium and Triazolium Side-Chain Polymethacrylates Obtained by Controlled Alkylation of the Corresponding Azole Derivatives

et al. 2015

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“…Thiopeptide biosynthesis operons also are wide spread in Actinobacteria, suggesting that these antibiotics have an important ecological role in nature. Another such thiopeptide compound, cyclothiazomycin B1, has been reported to have heat-stable antibiotic properties and to control fungal plant pathogens via disruption of cell wall chitin molecules (Mizuhara et al, 2011) and inhibition of RNA polymerase (Hasimoto et al, 2006). The size of the novel thiopeptide identified in our study, as well as fragmentation analysis of fractions in which it was present, revealed several amino-acid mass shifts corresponding to the sequence of the predicted thiopeptide and support the connection of the compound to the thiopeptide gene cluster.…”

Section: Discussionmentioning

confidence: 99%

Microbial and biochemical basis of a Fusarium wilt-suppressive soil

et al. 2015

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Crops lack genetic resistance to most necrotrophic pathogens. To compensate for this disadvantage, plants recruit antagonistic members of the soil microbiome to defend their roots against pathogens and other pests. The best examples of this microbially based defense of roots are observed in disease-suppressive soils in which suppressiveness is induced by continuously growing crops that are susceptible to a pathogen, but the molecular basis of most is poorly understood. Here we report the microbial characterization of a Korean soil with specific suppressiveness to Fusarium wilt of strawberry. In this soil, an attack on strawberry roots by Fusarium oxysporum results in a response by microbial defenders, of which members of the Actinobacteria appear to have a key role. We also identify Streptomyces genes responsible for the ribosomal synthesis of a novel heat-stable antifungal thiopeptide antibiotic inhibitory to F. oxysporum and the antibiotic’s mode of action against fungal cell wall biosynthesis. Both classical- and community-oriented approaches were required to dissect this suppressive soil from the field to the molecular level, and the results highlight the role of natural antibiotics as weapons in the microbial warfare in the rhizosphere that is integral to plant health, vigor and development.

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“…1) bind to elongation factor Tu (EF-Tu), blocking its aminoacyl-tRNA binding site, thus preventing peptide elongation (14)(15)(16). Beyond their intrinsic antibacterial properties, thiopeptides (especially thiostrepton and MP1) have been investigated for a variety of other applications, including antifungal (17), antiplasmodial (18)(19)(20)(21), and anticancer properties (22)(23)(24).…”

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confidence: 99%

Characterization of a Novel Plasmid-Borne Thiopeptide Gene Cluster in Staphylococcus epidermidis Strain 115

et al. 2014

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bThiopeptides are small (12-to 17-amino-acid), heavily modified peptides of bacterial origin. This antibiotic family, with more than 100 known members, is characterized by the presence of sulfur-containing heterocyclic rings and dehydrated residues within a macrocyclic peptide structure. Thiopeptides, including micrococcin P1, have garnered significant attention in recent years for their potent antimicrobial activity against bacteria, fungi, and even protozoa. Micrococcin P1 is known to target the ribosome; however, like those of other thiopeptides, its biosynthesis and mechanisms of self-immunity are poorly characterized. We have discovered an isolate of Staphylococcus epidermidis harboring the genes for thiopeptide production and self-protection on a 24-kb plasmid. Here we report the characterization of this plasmid, identify the antimicrobial peptide that it encodes, and provide evidence of a target replacement-mediated mechanism of self-immunity.

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Antifungal thiopeptide cyclothiazomycin B1 exhibits growth inhibition accompanying morphological changes via binding to fungal cell wall chitin

Cited by 50 publications

References 40 publications

High Efficiency Antimicrobial Thiazolium and Triazolium Side-Chain Polymethacrylates Obtained by Controlled Alkylation of the Corresponding Azole Derivatives

High Efficiency Antimicrobial Thiazolium and Triazolium Side-Chain Polymethacrylates Obtained by Controlled Alkylation of the Corresponding Azole Derivatives

Microbial and biochemical basis of a Fusarium wilt-suppressive soil

Characterization of a Novel Plasmid-Borne Thiopeptide Gene Cluster in Staphylococcus epidermidis Strain 115

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