FR220897 and FR220899, Novel Antifungal Lipopeptides from Coleophoma empetri No. 14573

Kanasaki, Ryuichi; Abe, Fumie; Kobayashi, Motoo; Katsuoka, Masaaki; Hashimoto, Michizane; Takase, Shigehiro; Tsurumi, Yasuhisa; Fujie, Akihiko; Hino, Motohiro; Hashimoto, Seiji; Hori, Yasuhiro

doi:10.1038/ja.2006.22

Cited by 26 publications

(14 citation statements)

References 13 publications

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“…A number of sulfated echinocandins, which differ not only in the amino acid constituents of the cyclic peptide but also in the acyl chain, have been isolated (Figure 4). FR209602, FR209603, FR209604, FR220897 and FR220899 have different methylation and hydroxylation modifications of amino acids in the cyclic peptide, with the same palmitoyl acyl chain as FR901379, 43,44 whereas FR190293 and FR227673 have the same cyclic peptide as FR901379, with different branched acyl side chains. 45 Furthermore, the sulfated hydroxyl residue presents at a different position in FR209602, FR209603 and FR209604 than those in other sulfated echinocandins.…”

Section: Other Sulfated Echinocandinsmentioning

confidence: 99%

Micafungin: a sulfated echinocandin

Hashimoto

2009

J Antibiot

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Micafungin is the second approved antifungal agent in the echinocandin series and is now used worldwide in chemotherapy for life-threatening fungal infections. It is water-soluble and is semi-synthesized from the acylated cyclic hexapeptide FR901379, a natural product from the fungus Coleophoma empetri F-11899, through enzymatic deacylation of FR901379, followed by chemical reacylation with the optimized N-acyl side chain. The water solubility of micafungin is ascribed to a sulfate moiety in the molecule. This feature differentiates micafungin from other echinocandin members. Micafungin is a potent inhibitor of 1,3-b-glucan synthase, an enzyme necessary for cell-wall synthesis of several fungal pathogens. The Journal of Antibiotics (2009) and Cryptococcus neoformans are a threat to human health. Incidences of these systemic fungal infections have increased significantly over the past few years. The major reasons for this dramatic increase are the extensive use of broad-spectrum antibiotics and the growing number of immunocompromised patients with acquired immunodeficiency syndrome (AIDS), cancer and transplants. 1,2 In the mid 1900s, few compounds, such as polyenes (for example, nystatin and amphotericin B) and flucytosine, were available for antifungal chemotherapy. Although the development of azole drugs started in the early 1970s, only a limited number of antifungal agents were available for treatment of life-threatening fungal infections. Moreover, the existing agents had disadvantages, such as the significant nephrotoxicity of amphotericin B 3 and the emergence of resistance to the azoles. 4 To overcome these defects, lipid formulations of polyenes were developed to reduce toxicity, and new triazoles (for example, voriconazole, ravuconazole and posaconazole) were developed to improve the antifungal spectra or susceptibility to azoleresistant isolates. 5 Despite a number of therapeutic advancements, there was a need to develop a new class of antifungal agents with novel mechanisms of action.

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Section: Other Sulfated Echinocandinsmentioning

confidence: 99%

Micafungin: a sulfated echinocandin

Hashimoto

2009

J Antibiot

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“…14573) from an unidentified decaying leaf from Tsushima Island, Japan and identified it as Coelophoma empetri . They fermented the strain to produce two water-soluble echinocandin analogues FR220897 and FR220899 (WF14573A and WF14573B) (Hori et al 2004, Kanasaki et al . 2006 ) ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Draft genome sequence of Annulohypoxylon stygium, Aspergillus mulundensis, Berkeleyomyces basicola (syn. Thielaviopsis basicola), Ceratocystis smalleyi, two Cercospora beticola strains, Coleophoma cylindrospora, Fusarium fracticaudum, Phialophora cf. hyalina, and Morchella septimelata

et al. 2018

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Draft genomes of the species Annulohypoxylon stygium, Aspergillus mulundensis, Berkeleyomyces basicola (syn. Thielaviopsis basicola), Ceratocystis smalleyi, two Cercospora beticola strains, Coleophoma cylindrospora, Fusarium fracticaudum, Phialophora cf. hyalina and Morchella septimelata are presented. Both mating types (MAT1-1 and MAT1-2) of Cercospora beticola are included. Two strains of Coleophoma cylindrospora that produce sulfated homotyrosine echinocandin variants, FR209602, FR220897 and FR220899 are presented. The sequencing of Aspergillus mulundensis, Coleophoma cylindrospora and Phialophora cf. hyalina has enabled mapping of the gene clusters encoding the chemical diversity from the echinocandin pathways, providing data that reveals the complexity of secondary metabolism in these different species. Overall these genomes provide a valuable resource for understanding the molecular processes underlying pathogenicity (in some cases), biology and toxin production of these economically important fungi.

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“…The echinocandins, the fourth group, are synthetically modified lipopeptides that originate from the natural compounds produced by fungi (15,16). The antifungal activity of echinocandins is attributed to selective inhibition of 1,3-␤-glucan synthesis by their function as noncompetitive inhibitors of 1,3-␤-glucan synthase (5,9,14,17,27). There is a need to identify unique antifungals for possible development of new therapeutics.…”

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Occidiofungin's Chemical Stability and In Vitro Potency against Candida Species

Ellis

Gosai

Emrick

et al. 2012

Antimicrob Agents Chemother

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Occidiofungin is a cyclic glyco-lipopeptide produced by Burkholderia contaminans. MICs against Candida species were between 0.5 and 2.0 g/ml. Occidiofungin retains its in vitro potency in the presence of 5% and 50% human serum with a minimal lethal concentration (MLC) of 2 and 4 g/ml, respectively. Time-kill and postantifungal effect (PAFE) experiments of occidiofungin against Candida albicans were performed. The results demonstrate that occidiofungin is fungicidal. Occidiofungin was also found to be a very stable molecule. It is resistant to extreme temperatures and pH and maintains its activity following exposure to gastric proteases.

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FR220897 and FR220899, Novel Antifungal Lipopeptides from Coleophoma empetri No. 14573

Cited by 26 publications

References 13 publications

Micafungin: a sulfated echinocandin

Micafungin: a sulfated echinocandin

Draft genome sequence of Annulohypoxylon stygium, Aspergillus mulundensis, Berkeleyomyces basicola (syn. Thielaviopsis basicola), Ceratocystis smalleyi, two Cercospora beticola strains, Coleophoma cylindrospora, Fusarium fracticaudum, Phialophora cf. hyalina, and Morchella septimelata

Occidiofungin's Chemical Stability and In Vitro Potency against Candida Species

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