Myxothiazol
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02569 |
| CAS | 76706-55-3 |
| Molecular Weight | 487.68 |
| Molecular Formula | C25H33N3O3S2 |
| Purity | 95% |
Online Inquiry
Description
Myxothiazol is an antibiotic produced by Myxococcus fulvus MXfl6. It has activity against filamentous fungi and individual gram-positive bacteria.
Specification
| Synonyms | Myxothiazol A |
| Storage | 2-8ºC |
| IUPAC Name | (2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-[2-[2-[(2S,3E,5E)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]hepta-2,6-dienamide |
| Canonical SMILES | CC(C)C=CC=CC(C)C1=NC(=CS1)C2=NC(=CS2)C=CC(C(C)C(=CC(=O)N)OC)OC |
| InChI | InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/b9-7+,10-8+,12-11+,22-13+/t17-,18+,21-/m0/s1 |
| InChI Key | XKTFQMCPGMTBMD-FYHMSGCOSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 679.6°C at 760 mmHg |
| Melting Point | 50-55°C |
| Density | 1.158 g/cm3 |
Reference Reading
1.Neisseria meningitis GNA1030 is a ubiquinone-8 binding protein.
Donnarumma D1, Golfieri G1, Brier S1, Castagnini M1, Veggi D1, Bottomley MJ1, Delany I1, Norais N2. FASEB J. 2015 Jun;29(6):2260-7. doi: 10.1096/fj.14-263954. Epub 2015 Feb 20.
Bexsero, a new vaccine against Neisseria meningitidis serogroup B (MenB), is composed of 3 main recombinant proteins and an outer membrane vesicle component. One of the main bactericidal antigens, neisseria heparin binding antigen (NHBA), is present as a fusion protein with the accessory protein genome-derived neisserial antigen (GNA) 1030 to further increase its immunogenicity. The gene encoding for GNA1030 is present and highly conserved in all Neisseria strains, and although orthologs are present in numerous species, its biologic function is unknown. Native mass spectrometry was used to demonstrate that GNA1030 forms a homodimer associated with 2 molecules of ubiquinone-8 (Ub8), a cofactor mainly involved in the electron transport chain and with antioxidant properties. Disc diffusion assays on the wild-type and knockout mutant of GNA1030, in the presence of various compounds, suggested that GNA1030 is not involved in oxidative stress or electron chain transport per se, although it contributes to constitutive refilling of the inner membrane with Ub8.
2.Deciphering the Nongenomic, Mitochondrial Toxicity of Tamoxifens As Determined by Cell Metabolism and Redox Activity.
Theodossiou TA1, Wälchli S2, Olsen CE1, Skarpen E3, Berg K1. ACS Chem Biol. 2016 Jan 15;11(1):251-62. doi: 10.1021/acschembio.5b00734. Epub 2015 Nov 30.
Tamoxifen is not only considered a very potent chemotherapeutic adjuvant for estrogen receptor positive breast cancers but also a very good chemo-preventive drug. Recently, there has been a rising amount of evidence for a nongenomic cytotoxicity of tamoxifen, even in estrogen receptor negative cells, which has greatly confounded researchers. Clinically, the side effects of tamoxifen can be very serious, ranging from liver steatosis to cirrhosis, tumorigenesis, or onset of porphyrias. Herein, we deciphered the nongenomic, mitochondrial cytotoxicity of tamoxifen in estrogen receptor positive MCF7 versus triple-negative MDA-MB-231 cells, employing the mitochondrial complex III quinoloxidizing-center inhibitor myxothiazol. We showed a role for hydroxyl-radical-mediated lipid peroxidation, catalyzed by iron, stemming from the redox interactions of tamoxifen quinoid metabolites with complex III, resulting in Fenton-capable reduced quinones. The role of tamoxifen semiquinone species in mitochondrial toxicity was also shown together with evidence of mitochondrial DNA damage.
3.Thiol-based antioxidants elicit mitochondrial oxidation via respiratory complex III.
Kolossov VL, Beaudoin JN, Ponnuraj N, DiLiberto SJ, Hanafin WP, Kenis PJ, Gaskins HR. Am J Physiol Cell Physiol. 2015 Jul 15;309(2):C81-91.
Excessive oxidation is widely accepted as a precursor to deleterious cellular function. On the other hand, an awareness of the role of reductive stress as a similar pathological insult is emerging. Here we report early dynamic changes in compartmentalized glutathione (GSH) redox potentials in living cells in response to exogenously supplied thiol-based antioxidants. Noninvasive monitoring of intracellular thiol-disulfide exchange via a genetically encoded biosensor targeted to cytosol and mitochondria revealed unexpectedly rapid oxidation of the mitochondrial matrix in response to GSH ethyl ester or N-acetyl-l-cysteine. Oxidation of the probe occurred within seconds in a concentration-dependent manner and was attenuated with the membrane-permeable ROS scavenger tiron. In contrast, the cytosolic sensor did not respond to similar treatments. Surprisingly, the immediate mitochondrial oxidation was not abrogated by depolarization of mitochondrial membrane potential or inhibition of mitochondrial GSH uptake.
4.A sustained deficiency of mitochondrial respiratory complex III induces an apoptotic cell death through the p53-mediated inhibition of pro-survival activities of the activating transcription factor 4.
Evstafieva AG1, Garaeva AA2, Khutornenko AA3, Klepikova AV4, Logacheva MD1, Penin AA4, Novakovsky GE2, Kovaleva IE3, Chumakov PM5. Cell Death Dis. 2014 Nov 6;5:e1511. doi: 10.1038/cddis.2014.469.
Generation of energy in mitochondria is subjected to physiological regulation at many levels, and its malfunction may result in mitochondrial diseases. Mitochondrial dysfunction is associated with different environmental influences or certain genetic conditions, and can be artificially induced by inhibitors acting at different steps of the mitochondrial electron transport chain (ETC). We found that a short-term (5 h) inhibition of ETC complex III with myxothiazol results in the phosphorylation of translation initiation factor eIF2α and upregulation of mRNA for the activating transcription factor 4 (ATF4) and several ATF4-regulated genes. The changes are characteristic for the adaptive integrated stress response (ISR), which is known to be triggered by unfolded proteins, nutrient and metabolic deficiency, and mitochondrial dysfunctions. However, after a prolonged incubation with myxothiazol (13-17 h), levels of ATF4 mRNA and ATF4-regulated transcripts were found substantially suppressed.
Recommended Products
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
