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Tautomycin

Names

[ CAS No. ]:
109946-35-2

[ 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...


More Articles

Related Compounds