Tunicamycin

Names

[ Name ]:
Tunicamycin

[Synonym ]:
TUNICAMYCIN,STREPTOMYCES LYSOSUPERFICUS
MFCD00065709
Tunicamycin Streptomyces sp.
(2E)-N-[(2S,3R,4R,5R,6R)-2-{[(2S,3S,4S,5R,6S)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-{(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-3,4-dihydroxytetrahydro-2-furanyl]-2-hydroxyethyl}-4,5-dihydroxytetrahydro-2H-pyran-3-yl]-12-methyl-2-tridecenamide
(2E)-N-[(2S,3R,4R,5R,6R)-2-{[(2S,3S,4S,5R,6S)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-{(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-2-hydroxyethyl}-4,5-dihydroxytetrahydro-2H-pyran-3-yl]-12-methyltridec-2-enamide (non-preferred name)
TUNICAMYCIN

Biological Activity

[Description]:

Tunicamycin is a N-acetylglucosamine containing antibiotic from Streptomyces lysosuperijkus which inhibits protein glycosylation.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Inflammation/Immunology

[References]

[1]. Nami B et al. Tunicamycin-induced endoplasmic reticulum stress reduces in vitro subpopulation and invasion of CD44+/CD24- phenotype breast cancer stem cells. Exp Toxicol Pathol. 2016 Aug;68(7):419-26.

[2]. Guo Q et al. Tunicamycin Aggravates Endoplasmic Reticulum Stress and Airway Inflammation via PERK-ATF4-CHOP Signaling in a Murine Model of Neutrophilic Asthma. J Asthma. 2016 Jul 6

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
234 - 235ºC

[ Molecular Formula ]:
C₃₉H₆₄N₄O₁₆(n=₁₀)

[ Molecular Weight ]:
844.94 (n=10)

[ PSA ]:
311.82000

[ LogP ]:
2.58

[ Index of Refraction ]:
1.617

[ Storage condition ]:
2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YO7980200

CHEMICAL NAME :: Tunicamycin

CAS REGISTRY NUMBER :: 11089-65-9

LAST UPDATED :: 199710

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 500 ug/kg

SEX/DURATION :: female 6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Cells - not otherwise specified

DOSE/DURATION :: 4 ug/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: 39,1148,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - E0225 No. of Facilities: 10 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 80 (estimated) No. of Female Employees: 30 (estimated)

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 ]:
28

[ Safety Phrases ]:
28-37/39-45

[ RIDADR ]:
UN 3462 6

[ WGK Germany ]:
3

[ RTECS ]:
YO7980200

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
29419090

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