| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| Other Sizes |
|
| Targets |
Macrolide antibiotic
|
|---|---|
| ln Vitro |
When pure CYP107W1 and oligomycin C interact, type I binding occurs, with a Kd value of 14.4 μM [2].
|
| Enzyme Assay |
Streptomyces avermitilis contains 33 cytochrome P450 genes in its genome, many of which play important roles in the biosynthesis process of antimicrobial agents. Here, we characterized the biochemical function and structure of CYP107W1 from S. avermitilis, which is responsible for the 12-hydroxylation reaction of oligomycin C. CYP107W1 was expressed and purified from Escherichia coli. Purified proteins exhibited the typical CO-binding spectrum of P450. Interaction of oligomycin C and oligomycin A (12-hydroxylated oligomycin C) with purified CYP107W1 resulted in a type I binding with Kd values of 14.4 ± 0.7 μM and 2.0 ± 0.1 μM, respectively. LC-mass spectrometry analysis showed that CYP107W1 produced oligomycin A by regioselectively hydroxylating C12 of oligomycin C. Steady-state kinetic analysis yielded a kcat value of 0.2 min(-1) and a Km value of 18 μM. The crystal structure of CYP107W1 was determined at 2.1 Å resolution. The overall P450 folding conformations are well conserved, and the open access binding pocket for the large macrolide oligomycin C was observed above the distal side of heme. This study of CYP107W1 can help a better understanding of clinically important P450 enzymes as well as their optimization and engineering for synthesizing novel antibacterial agents and other pharmaceutically important compounds.[2]
|
| Cell Assay |
During the screening program for fungicides, one actinomycete strain ECO 00047 was isolated with the potential activity against fungus. According to the morphology and analysis of the nucleotide sequence of the 16S rRNA gene (1500 bp) this isolate was identified as Streptomyces diastaticus. The active compounds were separated by silica gel column chromatography, Sephadex LH-20 gel filtration and then purified by flash chromatography on C18 (20-45 microm). The chemical structure of the bioactive compounds I and II were elucidated, based on the spectroscopic data of MS, IR, UV, 1H-NMR, 13C-NMR and X-ray single crystal diffraction analysis. Compounds I and II were identical with oligomycins A and C, the macrolide antibiotics which have been known to be produced by Streptomyces diastatochromogenes, S. libani and S. avermitilis. The two compounds exhibited a strong activity against Aspergillus niger, Alternaria alternata, Botrytis cinerea and Phytophthora capsici but no activity toward bacteria. Although the two above antibiotics were known, their isolation has so far not been reported from S. diastaticus.[1]
|
| Toxicity/Toxicokinetics |
mouse LD50 intraperitoneal 8300 ug/kg
|
| References |
|
| Additional Infomation |
See also: Oligomycin C (annotation moved to).
|
| Molecular Formula |
C45H74O10
|
|---|---|
| Molecular Weight |
775.06306
|
| Exact Mass |
774.528
|
| CAS # |
11052-72-5
|
| Related CAS # |
Oligomycin A;579-13-5;Oligomycin;1404-19-9;Oligomycin B;11050-94-5
|
| PubChem CID |
5472287
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.12g/cm3
|
| Boiling Point |
876.2ºC at 760mmHg
|
| Flash Point |
249.4ºC
|
| Vapour Pressure |
0mmHg at 25°C
|
| Index of Refraction |
1.535
|
| LogP |
6.767
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
10
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
55
|
| Complexity |
1340
|
| Defined Atom Stereocenter Count |
17
|
| SMILES |
CC[C@H]1C=CC=CC[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C=CC(=O)OC2[C@@H](C)C(OC3([C@@H]2C)CC[C@H](C)[C@H](C[C@H](O)C)O3)CC1 |t:3,5,30,&1:2,8,10,12,16,18,20,24,26,28,36,41,45,47,49|
|
| InChi Key |
CMMLZMMKTYEOKV-HQCSJJBPSA-N
|
| InChi Code |
InChI=1S/C45H74O10/c1-12-35-17-15-13-14-16-26(3)39(48)30(7)41(50)32(9)43(52)33(10)42(51)31(8)40(49)27(4)18-21-38(47)53-44-29(6)36(20-19-35)54-45(34(44)11)23-22-25(2)37(55-45)24-28(5)46/h13-15,17-18,21,25-37,39-40,43-44,46,48-49,52H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26+,27-,28?,29+,30-,31-,32+,33-,34-,35-,36-,37-,39-,40+,43-,44+,45-/m1/s1
|
| Chemical Name |
(1S,4E,5'R,6R,6'R,7S,8R,10S,11R,12R,14R,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,15-trihydroxy-6'-(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]-3,9,13-trione
|
| Synonyms |
Oligomycin C; 12-deoxyoligomycin A; 11052-72-5; Oligomycin A, 12-deoxy-; 4F7MA81184; (-)-Oligomycin C; (1R,4E,5'S,6S,6'S,7R,8S,10R,11S,12S,14S,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,15-trihydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione; UNII-4F7MA81184;
|
| 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 | 1.2902 mL | 6.4511 mL | 12.9022 mL | |
| 5 mM | 0.2580 mL | 1.2902 mL | 2.5804 mL | |
| 10 mM | 0.1290 mL | 0.6451 mL | 1.2902 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
