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Oligomycin Complex

(Synonyms: 寡霉素) 目录号 : GC16533

寡霉素复合物(Oligomycin complex)由寡霉素A、B和C的混合物组成。

Oligomycin Complex Chemical Structure

Cas No.:1404-19-9

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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment 1 [1]:

Cell lines

R-HepG2 and HepG2 cells

Preparation method

Cells were treated with oligomycin at the concentration indicated or medium alone at 37°C, 5% CO2 for 24 h.

Reaction Conditions

0-50μg/ml; 24h

Applications

Oligomycin induced mitochondrial depolarization in R-HepG2 and HepG2 cells.

Cell experiment 2 [2]:

Cell lines

HT29 cell

Preparation method

Cells were cultured with different concentrations of oligomycin A for 12,24,36 and 48 h.

Reaction Conditions

0-16 μM;12-48 h

Applications

Oligomycin promotes HT29 cell survival and proliferation.

References:

[1]. Li YC, Fung KP, et,al. Mitochondria-targeting drug oligomycin blocked P-glycoprotein activity and triggered apoptosis in doxorubicin-resistant HepG2 cells. Chemotherapy. 2004 Jun;50(2):55-62. doi: 10.1159/000077803. PMID: 15211078.

[2]. Li X, Tian R, et,al. Oligomycin A promotes radioresistance in HT29 colorectal cancer cells and its mechanisms. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2021 Feb 28;46(2):113-120. English, Chinese. doi: 10.11817/j.issn.1672-7347.2021.200063. PMID: 33678646.

产品描述

Oligomycin complex consists of a blend of oligomycins A, B, and C. Oligomycin is a class of similar 26-membered macrolide antibiotics isolated from Streptomyces amylase chromogenes. Oligomycin has antifungal activity, oxidative phosphorylation inhibition and insecticidal activity[1].Oligomycin A primarily exerts its inhibitory effect on mitochondrial oxidative phosphorylation by blocking the proton channel (F0 subunit) of ATP synthase, thus inhibiting ATP synthesis. Additionally, it reduces the compensatory increase in oxidative phosphorylation in tumor cells, leading to a decrease in cellular glycolysis levels[2-4].Oligomycin B acts as a non-selective inhibitor of ATP synthases, effectively slowing down ATP depletion in cases of myocardial ischemia. Oligomycin C is an inhibitor of mitochondrial F1F0-ATP synthase, which induces more sensitive cell death and shifts the cell death pattern from apoptosis to necrosis.

Oligomycin(0-50µg/ml; 24h) induced mitochondrial membrane depolarization and cytochrome c release in HepG2 and R-HepG2 cells[5].Oligomycin A(0-16 µM;12-48 h) promotes HT29 cell survival and proliferation[6]. In A549 cells, 100 ng/ml Oligomycin could completely inhibit OXPHOS phosphorylation activity in 1 hour and stimulate various levels of glycolysis gains[7]. 5 µg/ml Oligomycin could inhibit the F0 part of H+-ATP-synthase, and strongly suppress cytochrome c release and apoptosis in Hela cells induced by TNF[8]. Oligomycin B(1 µM) induced vasodilations that were 39-61% smaller in sulfonylurea receptor 2 null (SUR2(nl)) than in SUR2 wild-type (SUR2(wt)) arteries[9].

References:
[1]. SMITH RM, PETERSON WH, et,al.Oligomycin, a new antifungal antibiotic. Antibiot Chemother (Northfield). 1954 Sep;4(9):962-70. PMID: 24543225.
[2]. Vestergaard M, NØhr-Meldgaard K, et al. Inhibition of the ATP synthase eliminates the intrinsic resistance of Staphylococcus aureustowards polymyxins[J].mBio, 2017, 8(5): e01114-17.
[3]. Untereiner AA, Pavlidou A, et al. Drug resistance induces the upregulation of H2S-producing enzymes in HCT116 colon cancer cells[J].Biochem Pharmacol, 2018, 149: 174-185.
[4]. Ruas JS, Siqueira-Santos ES, et al. High glycolytic activity of tumor cells leads to underestimation of electron transport system capacity when mitochondrial ATP synthase is inhibited[J].Sci Rep, 2018, 8(1): 17383.
[5]. Li YC, Fung KP, et,al. Mitochondria-targeting drug oligomycin blocked P-glycoprotein activity and triggered apoptosis in doxorubicin-resistant HepG2 cells. Chemotherapy. 2004 Jun;50(2):55-62. doi: 10.1159/000077803. PMID: 15211078.
[6]. Li X, Tian R, et,al. Oligomycin A promotes radioresistance in HT29 colorectal cancer cells and its mechanisms. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2021 Feb 28;46(2):113-120. English, Chinese. doi: 10.11817/j.issn.1672-7347.2021.200063. PMID: 33678646.
[7]. Hao W, Chang CP, et al. Oligomycin-induced bioenergetic adaptation in cancer cells with heterogeneous bioenergetic organization. J Biol Chem. 2010 Apr 23;285(17):12647-54. doi: 10.1074/jbc.M109.084194. Epub 2010 Jan 28. PMID: 20110356; PMCID: PMC2857128.
[8]. Shchepina LA, Pletjushkina OY, et al. Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis. Oncogene. 2002 Nov 21;21(53):8149-57. doi: 10.1038/sj.onc.1206053. PMID: 12444550.
[9]. Adebiyi A, McNally EM, et al. Vasodilation induced by oxygen/glucose deprivation is attenuated in cerebral arteries of SUR2 null mice. Am J Physiol Heart Circ Physiol. 2011 Oct;301(4):H1360-8. doi: 10.1152/ajpheart.00406.2011. Epub 2011 Jul 22. PMID: 21784985; PMCID: PMC3197357.

寡霉素复合物(Oligomycin complex)由寡霉素A、B和C的混合物组成。寡霉素是从链霉菌淀粉酶色素中分离出来的一类类似26元大环内酯类抗生素。寡霉素具有抗真菌、氧化磷酸化抑制和杀虫活性[1-2]。寡霉素A主要通过阻断ATP合酶的质子通道(F0亚基),抑制ATP的合成来发挥其对线粒体氧化磷酸化的抑制作用。此外,它减少了肿瘤细胞中氧化磷酸化的代偿性增加,导致细胞糖酵解水平降低[3-5]。寡霉素B作为ATP合酶的非选择性抑制剂,在心肌缺血时有效减缓ATP的消耗。寡霉素C是一种线粒体F1F0-ATP合成酶抑制剂,可诱导更敏感的细胞死亡,并将细胞死亡模式从凋亡转变为坏死。

Oligomycin诱导HepG2和R-HepG2细胞线粒体膜去极化和细胞色素c释放[5]。Oligomycin A(0-16 µM;12-48 h)促进HT29细胞存活和增殖[6]。100 ng/ml Oligomycin在A549细胞中可在1小时内完全抑制OXPHOS磷酸化活性,并刺激不同程度的糖酵解增益[7]。5 µg/ml寡霉素可抑制H+- ATP合酶F0部分,强烈抑制TNF诱导的Hela细胞细胞色素c的释放和凋亡[8]。寡霉素B(1 µM)诱导的血管舒张在SUR2(nl)中比在SUR2野生型动脉中减少39-61%[9]。

Chemical Properties

Cas No. 1404-19-9 SDF
别名 寡霉素
Canonical SMILES O=C([C@H]([C@@H]([C@H](C([C@](C)([C@@H]([C@H](C/C=C/C=C/[C@]([H])(CC[C@@]1([C@@H]([C@]([H])(O2)[C@H]([C@@]3(O1)C(C[C@H]([C@]([H])(O3)C[C@H](C)O)C)=O)C)C)[H])CC)C)O)O)=O)C)O)C)[C@@H]([C@H]([C@@H](/C=C/C2=O)C)O)C.O=C([C@H]([C@@H]([C@H](C([C@](C)([C@@H]([C@H
分子式 C45H74O11 for Oligomycin A; C45H72O12 for Oligomycin B; C45H74O10 for Oligomycin C. 分子量 791.06 for Oligomycin A; 805.1 for Oligomycin B; 775.1 for Oligomycin C.
溶解度 ≤30mg/ml in ethanol;20mg/ml in DMSO;30mg/ml in dimethyl formamide 储存条件 Store at -20°C, protect from light
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1 mM 1.2641 mL 6.3206 mL 12.6413 mL
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10 mM 0.1264 mL 0.6321 mL 1.2641 mL
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