Echinomycin and Related Quinoxaline Antibiotics

Waring, Michael J.

doi:10.1007/978-1-349-12356-8_7

Cited by 23 publications

(22 citation statements)

References 76 publications

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“…One peptide complex has compounds of masses 1053 and 1102 Da. These masses are identical to components of kakadumycin and echinomycin, which are DNAintercalating antibiotics (Waring, 1979;Castillo et al, 2003) found as products in various streptomycetes. However, these inhibitory compounds are different from coronamycin, kakadumycin and echinomycin; amino acid analyses indicate that they contain leucine, tyrosine, isoleucine and other amino acids and that they are novel.…”

Section: Other Inhibitory Compounds Of Streptomyces Sp Msu-2110mentioning

confidence: 58%

“…This type of peptide antibiotic has been described by us and others, exemplified by the pseudomycins and cryptocandins (Ballio et al, 1994;Strobel et al, 1999;Miller et al, 1998). It is to be noted that other highly functionalized peptides have been virtually inseparable, as with commercially available echinomycin, which contains a family of related compounds (Waring, 1979;Castillo et al, 2003). It is important to note the strongly hydrophobic nature of coronamycin, imparted by the lipid component and the three leucine residues.…”

Section: Chemical Characterization Of Coronamycinmentioning

confidence: 86%

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Coronamycins, peptide antibiotics produced by a verticillate Streptomyces sp. (MSU-2110) endophytic on Monstera sp.

et al. 2004

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Coronamycin is a complex of novel peptide antibiotics with activity against pythiaceous fungi and the human fungal pathogen Cryptococcus neoformans. It is also active against the malarial parasite, Plasmodium falciparum, with an IC 50 of 9?0 ng ml "1. Coronamycin is produced by a verticillate Streptomyces sp. isolated as an endophyte from an epiphytic vine, Monstera sp., found in the Manu region of the upper Amazon of Peru. Bioassay-guided fractionation of the fermentation broths of this endophyte on silica gel and HPLC chromatography yielded two principal, inseparable, peptides with masses of 1217?9 and 1203?8 Da. Three other minor, but related components, are also present in the preparation. Amino acid analysis of coronamycin revealed residues of component 1, component 2, methionine, tyrosine and leucine at a ratio of 2 : 2 : 1 : 1 : 3. Other compounds with antifungal activities are also produced by this endophytic streptomycete.

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Section: Other Inhibitory Compounds Of Streptomyces Sp Msu-2110mentioning

confidence: 58%

Section: Chemical Characterization Of Coronamycinmentioning

confidence: 86%

Coronamycins, peptide antibiotics produced by a verticillate Streptomyces sp. (MSU-2110) endophytic on Monstera sp.

et al. 2004

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“…The major antibiotic product produced by this organism is kakadumycin A, a compound closely related to the previously described antibiotic echinomycin (and to triostin). Because kakadumycin A appears to be closely related to echinomycin, this report not only describes the isolation of this novel compound but demonstrates that kakadumycin A is structurally distinct from echinomycin [2]. Echinomycin (or quinomycin) is a well known quinoxaline antibiotic whose mode of action is to inhibit DNA-directed enzymatic RNA synthesis [3,4].…”

Section: Introductionmentioning

confidence: 98%

Kakadumycins, novel antibiotics fromStreptomycessp. NRRL 30566, an endophyte ofGrevillea pteridifolia

Castillo

Harper

Strobel

et al. 2003

FEMS Microbiology Letters

226

113

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An endophytic streptomycete (NRRL 30566) is described and partially characterized from a fern-leaved grevillea (Grevillea pteridifolia) tree growing in the Northern Territory of Australia. This endophytic streptomycete produces, in culture, novel antibiotics - the kakadumycins. Methods are outlined for the production and chemical characterization of kakadumycin A and related compounds. This antibiotic is structurally related to a quinoxaline antibiotic, echinomycin. Each contains, by virtue of their amino acid compositions, alanine, serine and an unknown amino acid. Other biological, spectral and chromatographic differences between these two compounds occur and are given. Kakadumycin A has wide spectrum antibiotic activity, especially against Gram-positive bacteria, and it generally displays better bioactivity than echinomycin. For instance, against Bacillus anthracis strains, kakadumycin A has minimum inhibitory concentrations of 0.2-0.3 microg x ml(-1) in contrast to echinomycin at 1.0-1.2 microg x ml(-1). Both echinomycin and kakadumycin A have impressive activity against the malarial parasite Plasmodium falciparum with LD(50)s in the range of 7-10 ng x ml(-1). In macromolecular synthesis assays both kakadumycin A and echinomycin have similar effects on the inhibition of RNA synthesis. It appears that the endophytic Streptomyces sp. offer some promise for the discovery of novel antibiotics with pharmacological potential.

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“…These compounds have a twofold medicinal interest as they exhibit both extreme potency against tumors and activity against reverse transcriptase. They are structurally related to the quinoxaline family, comprising antibiotics such as echinomycin and triostin (Waring, 1993), and share a similar mode of DNA binding characterized by bisintercalation (Huang et al, 1982). However, luzopeptin binds to DNA at least one order of magnitude more strongly than echinomycin (K a $ 10 7 M À1 ) and can reduce the mobility of DNA in nondenaturing polyacrylamide gels, which has led to the speculation that luzopeptin might form covalent complexes with DNA (Fox et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

The binding mode of the DNA bisintercalator luzopeptin investigated using atomic force microscopy

Berge

Haken

Waring

et al. 2003

Journal of Structural Biology

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Echinomycin and Related Quinoxaline Antibiotics

Cited by 23 publications

References 76 publications

Coronamycins, peptide antibiotics produced by a verticillate Streptomyces sp. (MSU-2110) endophytic on Monstera sp.

Coronamycins, peptide antibiotics produced by a verticillate Streptomyces sp. (MSU-2110) endophytic on Monstera sp.

Kakadumycins, novel antibiotics fromStreptomycessp. NRRL 30566, an endophyte ofGrevillea pteridifolia

The binding mode of the DNA bisintercalator luzopeptin investigated using atomic force microscopy

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