Myxothiazol

Names

[ Name ]:
Myxothiazol

[Synonym ]:
2,6-Heptadienamide,7-(2'-((1S,2E,4E)-1,6-dimethyl-2,4-heptadienyl)(2,4'-bithiazol)-4-yl)-3,5-dimethoxy-4-methyl-,(2E,4R,5S,6E)
MFCD00043397
MYXOTHIAZOL
7-(2
5-dimethoxy-4-methyl
2,6-Heptadienamide,7-(2'-(1,6-dimethyl-2,4-heptadienyl)(2,4'-bithiazol)-4-yl)-3,5-dimethoxy-4-methyl

Biological Activity

[Description]:

Myxothiazol, an antifungal antibiotic, is a mitochondrial electron transport chain complex III (bc1 complex) inhibitor. Myxothiazol inhibits the growth of many yeasts and fungi at concentrations between 0.01 and 3 μg/ml[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

Myxothiazol inhibits the growth of many yeasts and fungi at concentrations between 0.01 and 3 μg/ml[2]. Myxothiazol binds to the ubiquinol oxidation site Qo of complex III and blocks electron transfer from ubiquinol to cytochrome b and thus inhibits complex III activity[3].

[In Vivo]

Myxothiazol (i.p.; 0.56 mg/kg; daily for 4 days)-induced complex III inhibition can be induced in mice for four days in a row without overt hepatotoxicity or lethality[3]. Animal Model: C57Bl/J6 mice[3] Dosage: 0.56 mg/kg Administration: I.p.; 24 hours intervals for at most 4 times Result: A reversible complex III activity decrease to 50% of control value occurred at 2 h post-injection. At 74 h only minor histological changes in the liver were found, supercomplex formation was preserved and no significant changes in the expression of genes indicating hepatotoxicity or inflammation were found.

[References]

[1]. Thierbach G, et al. Myxothiazol, a new antibiotic interfering with respiration. Antimicrob Agents Chemother. 1981;19(4):504-507.

[2]. von Jagow G,et al. 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;259(10):6318-6326.

[3]. Davoudi M, et al. A mouse model of mitochondrial complex III dysfunction induced by myxothiazol. Biochem Biophys Res Commun. 2014;446(4):1079-1084.

Chemical & Physical Properties

[ Density]:
1.158g/cm3

[ Boiling Point ]:
679.6ºC at 760 mmHg

[ Molecular Formula ]:
C₂₅H₃₃N₃O₃S₂

[ Molecular Weight ]:
487.67800

[ Flash Point ]:
364.8ºC

[ Exact Mass ]:
487.19600

[ PSA ]:
143.81000

[ LogP ]:
6.51870

[ Index of Refraction ]:
1.584

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QH7580000

CHEMICAL NAME :: 2,6-Heptadienamide, 7-(2'-(1,6-dimethyl-2,4-heptadienyl)(2,4'-bithiazol)- 4-yl)-3,5-dimethoxy- 4-methyl-

CAS REGISTRY NUMBER :: 76706-55-3

LAST UPDATED :: 199307

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C25-H33-N3-O3-S2

MOLECULAR WEIGHT :: 487.73

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 33,1474,1980

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
28

[ Safety Phrases ]:
28-36/37-45

[ RIDADR ]:
UN 3462 6.1/PG 1

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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