Myxothiazol
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MedKoo CAT#: 564035

CAS#: 76706-55-3

Description: Myxothiazol is an inhibitor of mitochondrial respiratory chain complexes III. Myxothiazol induces transcription of the p53-responsive SESN2 gene that plays an important role in stress response and homeostatic regulation.

Chemical Structure

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Myxothiazol
CAS# 76706-55-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 564035
Name: Myxothiazol
CAS#: 76706-55-3
Chemical Formula: C25H33N3O3S2
Exact Mass: 487.20
Molecular Weight: 487.677
Elemental Analysis: C, 61.57; H, 6.82; N, 8.62; O, 9.84; S, 13.15

Price and Availability

Size Price Availability Quantity
1mg USD 350 2 Weeks
5g USD 950 2 Weeks
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Synonym: Myxothiazol

IUPAC/Chemical Name: (2Z,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

InChi Key: XKTFQMCPGMTBMD-ZDBABOMLSA-N

InChi Code: 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

SMILES Code: O=C(N)/C=C(OC)/[C@H](C)[C@@H](OC)/C=C/C1=CSC(C2=CSC([C@H](/C=C/C=C/C(C)C)C)=N2)=N1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#S20G11M07
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Myxothiazol, an antifungal antibiotic, is a mitochondrial electron transport chain complex III (bc1 complex) inhibitor.
In vitro activity: Myxothiazol, a new antibiotic from the myxobacterium Myxococcus fulvus, inhibited the growth of many yeasts and fungi at concentrations between 0.01 and 3 micrograms/ml. It was generally inactive against bacteria. The inhibitory effect was cytostatic. Reference: Antimicrob Agents Chemother. 1981 Apr;19(4):504-7. https://pubmed.ncbi.nlm.nih.gov/7247372/
In vivo activity: This study developed a mouse model of biochemically induced and reversible CIII inhibition using myxothiazol. This study administered myxothiazol intraperitoneally at a dose of 0.56 mg/kg to C57Bl/J6 mice every 24 h and assessed CIII activity, histology, lipid content, supercomplex formation, and gene expression in the livers of the mice. Reference: Biochem Biophys Res Commun. 2014 Apr 18;446(4):1079-84. https://pubmed.ncbi.nlm.nih.gov/24661880/

Preparing Stock Solutions

The following data is based on the product molecular weight 487.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. von Jagow G, Ljungdahl PO, Graf P, Ohnishi T, Trumpower BL. An inhibitor of mitochondrial respiration which binds to cytochrome b and displaces quinone from the iron-sulfur protein of the cytochrome bc1 complex. J Biol Chem. 1984 May 25;259(10):6318-26. PMID: 6327677. 2. Thierbach G, Reichenbach H. Myxothiazol, a new antibiotic interfering with respiration. Antimicrob Agents Chemother. 1981 Apr;19(4):504-7. doi: 10.1128/AAC.19.4.504. PMID: 7247372; PMCID: PMC181466. 3. Davoudi M, Kallijärvi J, Marjavaara S, Kotarsky H, Hansson E, Levéen P, Fellman V. A mouse model of mitochondrial complex III dysfunction induced by myxothiazol. Biochem Biophys Res Commun. 2014 Apr 18;446(4):1079-84. doi: 10.1016/j.bbrc.2014.03.058. Epub 2014 Mar 21. PMID: 24661880.
In vitro protocol: 1. von Jagow G, Ljungdahl PO, Graf P, Ohnishi T, Trumpower BL. An inhibitor of mitochondrial respiration which binds to cytochrome b and displaces quinone from the iron-sulfur protein of the cytochrome bc1 complex. J Biol Chem. 1984 May 25;259(10):6318-26. PMID: 6327677. 2. Thierbach G, Reichenbach H. Myxothiazol, a new antibiotic interfering with respiration. Antimicrob Agents Chemother. 1981 Apr;19(4):504-7. doi: 10.1128/AAC.19.4.504. PMID: 7247372; PMCID: PMC181466.
In vivo protocol: 1. Davoudi M, Kallijärvi J, Marjavaara S, Kotarsky H, Hansson E, Levéen P, Fellman V. A mouse model of mitochondrial complex III dysfunction induced by myxothiazol. Biochem Biophys Res Commun. 2014 Apr 18;446(4):1079-84. doi: 10.1016/j.bbrc.2014.03.058. Epub 2014 Mar 21. PMID: 24661880.

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1: Starkov AA, Fiskum G. Myxothiazol induces H(2)O(2) production from mitochondrial respiratory chain. Biochem Biophys Res Commun. 2001 Mar 2;281(3):645-50. PubMed PMID: 11237706.

2: Young TA, Cunningham CC, Bailey SM. Reactive oxygen species production by the mitochondrial respiratory chain in isolated rat hepatocytes and liver mitochondria: studies using myxothiazol. Arch Biochem Biophys. 2002 Sep 1;405(1):65-72. PubMed PMID: 12176058.

3: Weinig S, Mahmud T, Müller R. Markerless mutations in the myxothiazol biosynthetic gene cluster: a delicate megasynthetase with a superfluous nonribosomal peptide synthetase domain. Chem Biol. 2003 Oct;10(10):953-60. PubMed PMID: 14583261.

4: Lai B, Zhang L, Dong LY, Zhu YH, Sun FY, Zheng P. Impact of inhibition of Qo site of mitochondrial complex III with myxothiazol on persistent sodium currents via superoxide and protein kinase C in rat hippocampal CA1 cells. Neurobiol Dis. 2006 Jan;21(1):206-16. Epub 2005 Aug 2. PubMed PMID: 16081299.

5: Perlova O, Fu J, Kuhlmann S, Krug D, Stewart AF, Zhang Y, Müller R. Reconstitution of the myxothiazol biosynthetic gene cluster by Red/ET recombination and heterologous expression in Myxococcus xanthus. Appl Environ Microbiol. 2006 Dec;72(12):7485-94. Epub 2006 Sep 22. PubMed PMID: 16997979; PubMed Central PMCID: PMC1694261.

6: Midzak AS, Liu J, Zirkin BR, Chen H. Effect of myxothiazol on Leydig cell steroidogenesis: inhibition of luteinizing hormone-mediated testosterone synthesis but stimulation of basal steroidogenesis. Endocrinology. 2007 Jun;148(6):2583-90. Epub 2007 Mar 1. PubMed PMID: 17332065.

7: Sandmann A, Frank B, Müller R. A transposon-based strategy to scale up myxothiazol production in myxobacterial cell factories. J Biotechnol. 2008 Jun 30;135(3):255-61. doi: 10.1016/j.jbiotec.2008.05.001. Epub 2008 May 13. PubMed PMID: 18555551.

8: Davoudi M, Kallijärvi J, Marjavaara S, Kotarsky H, Hansson E, Levéen P, Fellman V. A mouse model of mitochondrial complex III dysfunction induced by myxothiazol. Biochem Biophys Res Commun. 2014 Apr 18;446(4):1079-84. doi: 10.1016/j.bbrc.2014.03.058. Epub 2014 Mar 21. PubMed PMID: 24661880.