Tautomycin

Modify Date: 2024-01-06 20:29:38

Tautomycin Structure
Tautomycin structure
Common Name Tautomycin
CAS Number 109946-35-2 Molecular Weight 766.95500
Density 1.18g/cm3 Boiling Point 854.3ºC at 760mmHg
Molecular Formula C41H66O13 Melting Point N/A
MSDS Chinese USA Flash Point 247.5ºC
Symbol GHS06
GHS06
Signal Word Danger

 Use of Tautomycin


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].

 Names

Name Tautomycin from Streptomyces spiroverticillatus
Synonym More Synonyms

 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
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

Name: Tautomycin Material Safety Data Sheet
Synonym: None Known
CAS: 109946-35-2
Section 1 - Chemical Product MSDS Name:Tautomycin Material Safety Data Sheet
Synonym:None Known

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
109946-35-2 Tautomycin unlisted
Hazard Symbols: T+
Risk Phrases: 28

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Very toxic if swallowed.The toxicological properties of this material have not been fully investigated.Mutagen.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May be fatal if swallowed. May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
Laboratory experiments have resulted in mutagenic effects.

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Deep freeze (below -20C).

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 109946-35-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C41H66O13
Molecular Weight: 766.4542

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 109946-35-2: WX1000000 LD50/LC50:
CAS# 109946-35-2: Oral, mouse: LD50 = 7500 ug/kg.
Carcinogenicity:
Tautomycin - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION


Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T+
Risk Phrases:
R 28 Very toxic if swallowed.
Safety Phrases:
S 1 Keep locked up.
S 28A After contact with skin, wash immediately with
plenty of water.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 109946-35-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 109946-35-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 109946-35-2 is not listed on the TSCA inventory.
It is for research and development use only.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 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
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

 Precursor & DownStream

Precursor  1

DownStream  0

 Articles26

More 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...

 Synonyms

MFCD00236438
tautomycin
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