| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
ATP synthase; Antibiotic
|
|---|---|
| ln Vitro |
Four antibiotics (pamamycin, oligomycin A, oligomycin B and echinosporin) were isolated and characterized from the fermentation broth of the marine Streptomyces strains B8496 and B8739. Bioassays revealed that each of these compounds impaired motility and caused subsequent lysis of P. viticola zoospores in a dose- and time-dependent manner. Pamamycin displayed the strongest motility inhibitory and lytic activities (IC50 0.1 μg mL(-1)) followed by oligomycin B (IC50 0.15 and 0.2 μg mL(-1)) and oligomycin F (IC50 0.3 and 0.5 μg mL(-1)). Oligomycin A and echinosporin also showed motility inhibitory activities against the zoospores with IC50 values of 3.0 and 10.0 μg mL(-1), respectively. This is the first report of motility inhibitory and lytic activities of these antibiotics against zoospores of a phytopathogenic peronosporomycete. Structures of all the isolated compounds were determined based on detailed spectroscopic analysis.[2]
|
| ln Vivo |
Production of zoospores and bioassay[2]
For the isolation of sporangia of Plasmopara viticola, infected leaves of grapevine. The strain was maintained by continuous culturing on the lower surface of young grapevine leaves on Petri dishes containing 1.5% water agar at 25°C and 95% relative humidity (Islam and Tiedemann 2011; Islam, Tiedemann and Laatsch 2011). On the sixth day of cultivation, the sporangiophores containing the lemon-shaped sporangia were harvested into an Eppendorf vial by a micro-vacuum cleaner. The freshly harvested sporangia were separated from sporangiophores by filtration through a nylon sieve (50 mesh), washed twice with distilled water and then incubated in sterilized tap water (3 × 104 sporangia per mL) in the dark for 6 h at room temperature (23°C) to release zoospores. The zoospores remained motile up to 12 h in sterilized water, and they were used for the motility bioassay (Islam and Tahara 2001). Stock solutions of the antibiotics were first prepared in dimethyl sulfoxide (DMSO) and then diluted with distilled water. The final concentration of DMSO in the zoospore suspension never exceeded 1% (v/v), a condition that does not affect zoospore motility. The effects of compounds on motility and viability of zoospores were assayed using protocols described earlier (Islam et al.2005; Abdalla et al.2011; Islam, Tiedemann and Laatsch 2011). Motility of the zoospores was observed under a light microscope at 100-fold magnification. Quantification of time-course changes of motility and lysis of the zoospores were carried out as described earlier (Islam, Tiedemann and Laatsch 2011). Each treatment was replicated three times. The mean value % ±SE (standard error) of the affected spores in each treatment was calculated and the statistical significance was determined by one- and two-way Analysis of Varience (ANOVA) and t-test. Two-way ANOVA (see Table S1, Supporting Information) was used to test the significance of differences in motility inhibition and lytic activities of the antibiotics at different times and doses of treatment. The difference is considered statistically significant with a value of P < 0.05. |
| Cell Assay |
Scabrosin esters (SEs), which have been recently isolated from the lichen Xanthoparmelia scabrosa, belong to the epipolythiodioxopiperazine (ETP) class of secondary metabolites characterized by possession of a reactive disulfide bond. Colony forming assays show that these toxins are active against human tumor cell lines at nanomolar concentrations. Other members of the ETP class of toxins such as gliotoxin have been shown to induce apoptosis in cells, although the cellular target(s) of the ETP toxins is currently unknown. ETP toxins have been shown to inhibit a variety of enzymes via interaction with sensitive cysteine residues. Here we show that the typical scabrosin ester acetate butyrate induces early mitochondrial membrane hyperpolarization assessed by JC-1 staining accompanied by apoptotic cell death. The toxin lowers ATP in intact cells and inhibits the rate of ATP synthesis in permeabilzed cells. Comparison with the effects of the known ATP synthase inhibitor oligomycin B is consistent with ATP synthase as an early target in scabrosin ester-induced cell death.[1]
|
| Animal Protocol |
Production of zoospores and bioassay[2]
For the isolation of sporangia of Plasmopara viticola, infected leaves of grapevine. The strain was maintained by continuous culturing on the lower surface of young grapevine leaves on Petri dishes containing 1.5% water agar at 25°C and 95% relative humidity (Islam and Tiedemann 2011; Islam, Tiedemann and Laatsch 2011). On the sixth day of cultivation, the sporangiophores containing the lemon-shaped sporangia were harvested into an Eppendorf vial by a micro-vacuum cleaner. The freshly harvested sporangia were separated from sporangiophores by filtration through a nylon sieve (50 mesh), washed twice with distilled water and then incubated in sterilized tap water (3 × 104 sporangia per mL) in the dark for 6 h at room temperature (23°C) to release zoospores. The zoospores remained motile up to 12 h in sterilized water, and they were used for the motility bioassay (Islam and Tahara 2001). Stock solutions of the antibiotics were first prepared in dimethyl sulfoxide (DMSO) and then diluted with distilled water. The final concentration of DMSO in the zoospore suspension never exceeded 1% (v/v), a condition that does not affect zoospore motility. The effects of compounds on motility and viability of zoospores were assayed using protocols described earlier (Islam et al.2005; Abdalla et al.2011; Islam, Tiedemann and Laatsch 2011). Motility of the zoospores was observed under a light microscope at 100-fold magnification. Quantification of time-course changes of motility and lysis of the zoospores were carried out as described earlier (Islam, Tiedemann and Laatsch 2011). Each treatment was replicated three times. The mean value % ±SE (standard error) of the affected spores in each treatment was calculated and the statistical significance was determined by one- and two-way Analysis of Varience (ANOVA) and t-test. Two-way ANOVA (see Table S1, Supporting Information) was used to test the significance of differences in motility inhibition and lytic activities of the antibiotics at different times and doses of treatment. The difference is considered statistically significant with a value of P < 0.05. |
| Toxicity/Toxicokinetics |
mouse LD50 intraperitoneal 2900 ug/kg
|
| References |
|
| Additional Infomation |
Oligomycin B is an oligomycin with formula C45H72O12 that is oligomycin A in which the spirocyclic ring bearing the 2-hydroxypropyl substituent has been substituted by an oxo group at the carbon which is directly attached to the spirocentre. It is a nonselective inhibitor of the mitochondrial F1F0 ATP synthase. It has a role as an EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor. It is an oligomycin, a triketone and a pentol.
Oligomycin A, 28-oxo- has been reported in Apis cerana with data available. |
| Molecular Formula |
C45H72O12
|
|---|---|
| Molecular Weight |
805.04598
|
| Exact Mass |
804.502
|
| CAS # |
11050-94-5
|
| Related CAS # |
Oligomycin A;579-13-5;Oligomycin;1404-19-9;Oligomycin D;1404-59-7;Oligomycin C;11052-72-5
|
| PubChem CID |
76958645
|
| Appearance |
Typically exists as White to off-white solid at room temperature
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
911.4±65.0 °C at 760 mmHg
|
| Melting Point |
160-161℃
|
| Flash Point |
260.3±27.8 °C
|
| Vapour Pressure |
0.0±0.6 mmHg at 25°C
|
| Index of Refraction |
1.547
|
| LogP |
5.5
|
| Hydrogen Bond Donor Count |
5
|
| Hydrogen Bond Acceptor Count |
12
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
57
|
| Complexity |
1470
|
| Defined Atom Stereocenter Count |
18
|
| SMILES |
CC[C@@H]1C=CC=CC[C@H](C)[C@H]([C@@](C)(C(=O)[C@H](C)[C@H]([C@H](C)C(=O)[C@H](C)[C@H]([C@H](C)C=CC(=O)O[C@H]2[C@@H](C)[C@@H](CC1)O[C@]3([C@@H]2C)C(=O)C[C@@H](C)[C@@H](C[C@H](C)O)O3)O)O)O)O
|
| InChi Key |
QPRQJOHKNJIMGN-WVUAJZTGSA-N
|
| InChi Code |
InChI=1S/C45H72O12/c1-12-33-17-15-13-14-16-25(3)42(52)44(11,54)43(53)31(9)40(51)30(8)39(50)29(7)38(49)24(2)18-21-37(48)55-41-28(6)34(20-19-33)56-45(32(41)10)36(47)22-26(4)35(57-45)23-27(5)46/h13-15,17-18,21,24-35,38,40-42,46,49,51-52,54H,12,16,19-20,22-23H2,1-11H3/b14-13+,17-15+,21-18+/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34-,35-,38+,40+,41+,42-,44+,45+/m0/s1
|
| Chemical Name |
(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27S,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,3',9,13-tetrone
|
| Synonyms |
Oligomycin B; 11050-94-5; Oligomycin A, 28-oxo-; 387OE420H7; EINECS 234-275-5; BRN 5705502; (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27S,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-5',6'-dihydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,3',9,13(4'H)-tetrone; 28-OXOOLIGOMYCIN A;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2422 mL | 6.2108 mL | 12.4216 mL | |
| 5 mM | 0.2484 mL | 1.2422 mL | 2.4843 mL | |
| 10 mM | 0.1242 mL | 0.6211 mL | 1.2422 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
