PD 118,576: A new antitumor macrolide antibiotic.

Wilton, John H.; Hokanson, Gerard C.; French, James C.

doi:10.7164/antibiotics.38.1449

Cited by 26 publications

(17 citation statements)

References 9 publications

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“…1 Natural hygrolidin and bafilomycin derivatives differ in the substitution pattern of the polyketide backbone (C-2 and tetrahydropyran ring), as well as optional side chains. These well-known actinomyces metabolites are pharmacologically important, because of their biological activities including antiparasitic, antitumor and immunosuppressant, [2][3][4][5] together with bactericidal, fungicidal, insecticidal and herbicidal effects. [6][7][8] Bafilomycin A1 (2) is a highly potent and specific inhibitor of vacuolar ATPase enzymes, 9,10 and has a role as carrier type K + ionophore, 11 which has led to a considerable interest in these metabolites.…”

Section: Introductionmentioning

confidence: 99%

Hygrobafilomycin, a cytotoxic and antifungal macrolide bearing a unique monoalkylmaleic anhydride moiety, from Streptomyces varsoviensis

et al. 2010

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A new bafilomycin-type macrolide, named hygrobafilomycin (6), was isolated by a bioassay-guided selection and fractionation from a terrestrial actinomycete, Streptomyces varsoviensis, along with three known derivatives, bafilomycin D (3), C1 (4) and C2 (5). The structure of hygrobafilomycin was fully established by MS and NMR analyses, revealing a hygrolidin-bafilomycin hybrid with an unusual monoalkylmaleic anhydride moiety. Hygrobafilomycin (6) shows strong antifungal, antiproliferative and cytotoxic activities. In a panel of 40 tumor cell lines, compound 6 shows high cytotoxic potency (mean IC 50 ¼5.3 nM).

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Section: Introductionmentioning

confidence: 99%

Hygrobafilomycin, a cytotoxic and antifungal macrolide bearing a unique monoalkylmaleic anhydride moiety, from Streptomyces varsoviensis

et al. 2010

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“…Bafilomycins are 16-membered macrolides, to which various side chains are attached (at the lactone terminus C15), leading to the generic term bafiloid [162] . To this class, numerous structural groups are belonging: the concanamycins [163] , forma-micins [164] , hydrolidins [165] , leucanicidins [166] , PD-118576 [167] and micromonospolides [168] .…”

Section: Ts155mentioning

confidence: 99%

“…Albaflavenone (167), an unsaturated sesquiterpene ketone with a zizaene skeleton, was isolated from S. albidoflavus and reported as antibacterial agent with MIC of 8~10 µg/ml against Bacillus subtilis [262] . In our antitumor assay, albaflavenone [262] .…”

Section: Structure Activities Relationships Of Mansouramycinsmentioning

confidence: 99%

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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“…The bafilomycins, which are potent vacuolar ATPase inhibitors (Bowman et al 1988), display a wide spectrum of biological activities, e.g., antiviral (Uyeda et al 1995), cytotoxic (Wilton et al 1985), and insecticidal (Goetz et al 1985). No reports about the effects of bafilomycins on fungal radial growth and hyphal morphology have been published from other laboratories, although some investigators have recorded antifungal effects (Werner et al 1984;Bowman et al 1992).…”

mentioning

confidence: 94%

Streptomyces halstediiK122 produces the antifungal compounds bafilomycin B1 and C1

Frändberg

Petersson²,

Lundgren³

et al. 2000

Can. J. Microbiol.

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Streptomyces halstedii K122 was previously found to produce antifungal compounds on solid substrates that inhibit radial growth of fungi among Ascomycetes, Basidiomycetes, Deuteromycetes, Oomycetes, and Zygomycetes, and strongly affected hyphal branching and morphology. During growth of S. halstedii K122 in submerged culture, no antifungal activity could be detected. However, cultivation of S. halstedii in thin (1 mm) liquid substrate layers in large surface-area tissue culture flasks caused intense growth and sporulation of S. halstedii K122, and the biologically active compounds could be extracted from the mycelium with methanol. Antifungal compounds were purified using C18 solid phase extraction and silica gel column chromatography, and identified as bafilomycins B1 and C1, using 2D NMR and FAB MS. Production of bafilomycins, which are specific inhibitors of vacuolar ATPases, has not been reported from S. halstedii previously. Minimum inhibitory concentrations (MIC) of bafilomycins B1 and C1, amphotericin B, and nikkomycin Z were determined at pH 5.5 and 7.0 for the target fungi Aspergillus fumigatus, Mucor hiemalis, Penicillium roqueforti, and Paecilomyces variotii. Penicillium roqueforti was the most sensitive species to all the compounds investigated. The MIC values for amphotericin B were 0.5-4 micrograms.mL-1 for the fungi tested, and pH did not affect the toxicity. The MIC values for nikkomycin Z ranged from < 0.5 microgram.mL-1 for Mucor hiemalis to > 500 micrograms.mL-1 for Aspergillus fumigatus, and pH had no influence on toxicity. Bafilomycins B1 and C1 were equally active against the fungal species tested, with MIC values in the range of < 0.5-64 micrograms.mL-1. All fungi were more sensitive to both bafilomycin B1 and C1 at pH 7.0 than at pH 5.5.

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PD 118,576: A new antitumor macrolide antibiotic.

Cited by 26 publications

References 9 publications

Hygrobafilomycin, a cytotoxic and antifungal macrolide bearing a unique monoalkylmaleic anhydride moiety, from Streptomyces varsoviensis

Hygrobafilomycin, a cytotoxic and antifungal macrolide bearing a unique monoalkylmaleic anhydride moiety, from Streptomyces varsoviensis

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Streptomyces halstediiK122 produces the antifungal compounds bafilomycin B1 and C1

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