Oligomycin D
(Synonyms: 芦他霉素,26-Demethyloligomycin A) 目录号 : GC44506An inhibitor of mitochondrial F1FO-ATPase
Cas No.:1404-59-7
Sample solution is provided at 25 µL, 10mM.
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Oligomycin D is a macrolide antibiotic produced by several species of Streptomyces that inhibits the mitochondrial F1FO-ATPase and is used to uncouple oxidative phosphorylation from electron transport. [1] Oligomycin D is reported to inhibit K-Ras plasma membrane localization in MDCK cells with an IC50 value of 3.49 nM and is cytotoxic to SW620 colon cancer cells with an IC50 value of 36 µM.[2]
Reference:
[1]. Inoue, S., Mizutani, A., Sugita, R., et al. Purification and characterization of a novel protein activator of Ca2+/calmodulin-dependent protein kinase I. Biochemical and Biophysical Research Communications 215(3), 861-867 (1995).
[2]. Salim, A.A., Tan, L., Huang, X.-C., et al. Oligomycins as inhibitors of K-Ras plasma membrane localisation. Organic & Biomolecular Chemistry 14(2), 711-715 (2016).
Cas No. | 1404-59-7 | SDF | |
别名 | 芦他霉素,26-Demethyloligomycin A | ||
化学名 | (1S,2'R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,29R)-22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,29-octamethyl-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione | ||
Canonical SMILES | C[C@H](C[C@H]1[C@@H](C)CC[C@@]2(C[C@@H]([C@@]([H])([C@@H](O2)CC[C@@]([H])(CC)/C=C/C=C/C[C@@H](C)[C@H](O)[C@@](O)(C3=O)C)C)OC(/C=C/[C@H](C)[C@@H](O)[C@H](C)C([C@H](C)[C@@H](O)[C@@H]3C)=O)=O)O1)O | ||
分子式 | C44H72O11 | 分子量 | 777 |
溶解度 | Soluble in methanol, or in ethanol, or in DMSO, or in DMF | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.287 mL | 6.435 mL | 12.87 mL |
5 mM | 0.2574 mL | 1.287 mL | 2.574 mL |
10 mM | 0.1287 mL | 0.6435 mL | 1.287 mL |
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Mitochondrial signaling in Saccharomyces cerevisiae pseudohyphae formation induced by butanol
FEMS Yeast Res 2013 Jun;13(4):367-74.PMID:23448552DOI:10.1111/1567-1364.12039.
Yeasts growing limited for nitrogen source or treated with fusel alcohols form elongated cells--pseudohyphae. Absence of mitochondrial DNA or anaerobic conditions inhibits this process, but the precise role of mitochondria is not clear. We found that a significant percentage of pseudohyphal cells contained mitochondria with different levels of membrane potential within one cell. An uncoupler carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone (FCCP), but not the ATP-synthase inhibitor Oligomycin D, prevented pseudohyphal growth. Interestingly, repression of the MIH1 gene encoding phosphatase activator of the G2/M transition partially restores the ability of yeast to form pseudohyphal cells in the presence of FCCP or in the absence of mitochondrial DNA. At the same time, retrograde signaling (the one triggered by dysfunctional mitochondria) appeared to be a positive regulator of butanol-induced pseudohyphae formation: the deletion of any of the retrograde signaling genes (RTG1, RTG2, or RTG3) partially suppressed pseudohyphal growth. Together, our data suggest that two subpopulations of mitochondria are required for filamentous growth: one with high and another with low transmembrane potential. These mitochondria-activated signaling pathways appear to converge at Mih1p level.
[Construction of SPA7074-deficient mutant of biocontrol strain Streptomyces pactum Act12 and characterization of its secondary metabolites]
Wei Sheng Wu Xue Bao 2016 Dec 4;56(12):1883-91.PMID:29741854doi
Objective: To disrupt spa7074, which encodes a member of the TetR family transcriptional factors, in biocontrol strain Act12 and characterize the secondary metabolites in the mutant strain. Methods: We disrupted the gene spa7074 by homologous recombination. The secondary metabolites of the mutant strain Δspa7074 and Act12 were detected by HPLC. The structure was analyzed by MS and NMR. Results: Compared to the wild-type strain, the production of some unknown compounds in the mutant strain Δspa7074 increased obviously. We purified one of the compounds and identified as Oligomycin D by MS and NMR analysis. Conclusion: An oligomycin D-producing strain Δspa7074 was derived via genetic engineering.