Tautomycin

Names

[ Name ]:
Tautomycin

[Synonym ]:
MFCD00236438
tautomycin

Biological Activity

[Description]:

Tautomycin, an antifungal antibiotic isolated from the bacterium Streptomyces verticillatus, is a potent and specific inhibitor of protein phosphatases 1 and 2A and induces contraction of smooth muscle under Ca2+-free conditions, with Kiapp values of 0.16 nM and 0.4 nM for PP1 and PP2A, respectively[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphatase

Research Areas >> Inflammation/Immunology

[Target]

Kiapp: 0.16 nM (PP1), 0.4 nM (PP2A)[1].

[In Vitro]

MTC cell growth is inhibited in a dose-dependent manner by Tautomycin (0-1000 nM, 48 hours)[2]. NE markers ASCL1 and CgA in human MTC cells are decreased in a dose-dependent manner by Tautomycin (0-1000 nM, 48 hours)[2]. Cell Proliferation Assay[2] Cell Line: Human MTC cells Concentration: 0-1000 nM Incubation Time: 48 hours Result: Inhibited MTC cell growth in a dose-dependent manner. Western Blot Analysis[2] Cell Line: Human MTC cells Concentration: 0-1000 nM Incubation Time: 48 hours Result: Led to a dose-dependent decrease in the NE markers ASCL1 and CgA.

[References]

[1]. MacKintosh C, et al. Tautomycin from the bacterium Streptomyces verticillatus. Another potent and specific inhibitor of protein phosphatases 1 and 2A. FEBS Lett. 1990 Dec 17;277(1-2):137-40.

[2]. Adler JT, et al. Tautomycetin and tautomycin suppress the growth of medullary thyroid cancer cells via inhibition of glycogen synthase kinase-3beta. Mol Cancer Ther. 2009 Apr;8(4):914-20.

Chemical & Physical Properties

[ Density]:
1.18g/cm3

[ Boiling Point ]:
854.3ºC at 760mmHg

[ Molecular Formula ]:
C₄₁H₆₆O₁₃

[ Molecular Weight ]:
766.95500

[ Flash Point ]:
247.5ºC

[ Exact Mass ]:
766.45000

[ PSA ]:
192.19000

[ LogP ]:
4.78530

[ Vapour Pressure ]:
5.62E-34mmHg at 25°C

[ Index of Refraction ]:
1.527

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WX1000000

CHEMICAL NAME :: Tautomycin

CAS REGISTRY NUMBER :: 109946-35-2

LAST UPDATED :: 199410

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C42-H70-O12.3/2H2-O

MOLECULAR WEIGHT :: 793.00

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Human Leukocyte

DOSE/DURATION :: 1 mg/L

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: 41,932,1988

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
R28

[ Safety Phrases ]:
S22

[ RIDADR ]:
UN 3462 6.1/PG 2

[ RTECS ]:
WX1000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Characterization of the tautomycetin biosynthetic gene cluster from Streptomyces griseochromogenes provides new insight into dialkylmaleic anhydride biosynthesis.

J. Nat. Prod. 72(3) , 450-9, (2009)

Tautomycetin (TTN) is a highly potent and specific protein phosphatase inhibitor isolated from Streptomyces griseochromogenes. The biological activity of TTN makes it an important lead for drug discov...

The bifunctional glyceryl transferase/phosphatase OzmB belonging to the HAD superfamily that diverts 1,3-bisphosphoglycerate into polyketide biosynthesis.

J. Am. Chem. Soc. 128(32) , 10386-7, (2006)

The HAD superfamily protein OzmB from the oxazolomycin biosynthetic pathway is shown to divert the primary metabolite 1,3-diphosphoglycerate into the polyketide biosynthetic pathway as glycerate via l...

PR55 alpha, a regulatory subunit of PP2A, specifically regulates PP2A-mediated beta-catenin dephosphorylation.

J. Biol. Chem. 284 , 22649 - 22656, (2009)

A central question in Wnt signaling is the regulation of beta-catenin phosphorylation and degradation. Multiple kinases, including CKI alpha and GSK3, are involved in beta-catenin phosphorylation. Pro...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.