TUNICAMYCIN

Product Name: TUNICAMYCIN
CAS No.: 11089-65-9
Chemical Name: TUNICAMYCIN
Synonyms: isamycin;Nsc177382;Aids010655;TUNICAMYCIN;Aids-010655;TunicaMycin coMplex;Tunicamycin Mixture;TUNICAMYCIN USP/EP/BP;InSolution? Tunicamycin,;Tunicamycin (n= 8,9,10,11)
CBNumber: CB4211576
Molecular Formula: C37H60N4O16
Formula Weight: 816.89
MOL File: 11089-65-9.mol

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TUNICAMYCIN Property

Melting point:: 234-235℃ (decomposition)
alpha: D20 +52° (c = 0.5 in pyridine)
Flash point:: 87℃
storage temp.: 2-8°C
solubility: Soluble in methanol, ethanol, DMSO, or DMF
form: White to off-white solid
color: White
Sensitive: Moisture & Light Sensitive
BRN: 6888090
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey: YJQCOFNZVFGCAF-WPTOCQRYSA-N
EPA Substance Registry System: Tunicamycin (11089-65-9)

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Safety

Hazard Codes: T+,T
Risk Statements: 28
Safety Statements: 28-37/39-45
RIDADR: UN 3462 6.1/PG 2
WGK Germany: 3
RTECS: YO7980200
F: 8-10-18-21
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 29419090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 654380
Product name: Tunicamycin,
Purity: Tunicamycin,
Packaging: 10mg
Price: $230
Updated: 2024/03/01

Sigma-Aldrich

Product number: 654380
Product name: Tunicamycin,
Purity: Tunicamycin,
Packaging: 50mg
Price: $604
Updated: 2024/03/01

Alfa Aesar

Product number: J67401
Product name: Tunicamycin, 10 mg/ml in DMSO
Purity: sterile-filtered
Packaging: 1ml
Price: $485
Updated: 2024/03/01

Alfa Aesar

Product number: J62217
Product name: Tunicamycin
Purity: 95%
Packaging: 10mg
Price: $243
Updated: 2024/03/01

Cayman Chemical

Product number: 11445
Product name: Tunicamycin
Purity: ≥95% (mixture of isomers)
Packaging: 1mg
Price: $32
Updated: 2024/03/01

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TUNICAMYCIN Chemical Properties,Usage,Production

Description

Tunicamycin mixture is a mixture of tunicamycins with variable trans-2,3-unsaturated branched chain fatty acid (BFCA) chain lengths. Tunicamycins are anti-microbial agents that are active against Gram-positive bacteria, fungi, and viruses. They inhibit the N-acetylhexosamine (HexNAc) phosphotransferase family of enzymes in bacteria and prevent peptidoglycan biosynthesis. In eukaryotes, they inhibit N-acetylglucosamine (GlcNAc) phosphotransferase (GPT), preventing the first step in N-linked glycosylation and inducing the unfolded protein response and cell death. The cellular toxicity of tunicamycins is linked to the trans-2,3-unsaturated BCFA, and saturated BCFA-containing tunicamycin derivatives, such as TunR1 and TunR2 , have reduced toxicity. Tunicamycins impair glycosylation of the receptor tyrosine kinases EGFR, HER2, HER3, and IGF-1R, which prevents their translocation out of the endoplasmic reticulum and Golgi apparatus and reduces their protein levels and activity. Tunicamycin sensitizes EGFR inhibitor-resistant U251 glioma and Bx/PC-3 pancreatic adenocarcinoma cells to irradiation.

Chemical Properties

White solid

Uses

Tunicamycin has been widely used in the study of glycoprotein synthesis in various biological systems. During protein glycosylation, tunicamycin is noted to be an inhibitor of the transfer of saccharide moieties to dolichol during dolichol-linked glycoprotein synthesis. Dose-dependent inhibition of DNA synthesis may be related to the alteration of glycoproteins, which thereby affects the transport of thymidine into cells. Additionally, tunicamycin has been reported to prevent cell cycle progression in primary cultures of rat glial cells, as well as inhibit lipid-mediated protein glycosylation in chick or mouse fibroblasts in a dose-dependent manner.

Uses

The tunicamycins are a family of lipophilic nucleosides with fatty acids conjugated to an aminoglycoside group. The complex comprises analogues, tunicamycins I to X. This composition is typical of other products less precisely described as tunicamycins A to D. The tunicamycins act by blocking the formation of N-glycoside linkages to proteins via inhibition of formation of dolichol monophosphate from N-acetylglucosamine-1-phosphate. Tunicamycin blocks the synthesis of all N-linked glycoproteins (N-glycans) and causes cell cycle arrest in G1 phase. Tunicamycins are broadly active against prokaryotes, eukaryotes and viruses.

Uses

As a tool in studying glycoproteins in a wide variety of biological systems.

Definition

ChEBI: A mixture of antiviral nucleoside antibiotics produced by Streptomyces lysosuperificus. It contains at least 10 homologues comprising uracil, N-acetylglucosamine, an 11-carbon aminodialdose called tunicamine, and a fatty aci linked to the amino group of the tunicamine. The homologues vary in the composition of the fatty acid moiety.

General Description

Tunicamycin was first isolated from Streptomyces lysosuperificus based on its antiviral activity. It contains N-acetylglucosamine and inhibits glycoprotein biosynthesis, including virus membrane glycoproteins.

Biochem/physiol Actions

Cell permeable: yes

storage

+4°C

Purification Methods

The components of this nucleotide antibiotic from Streptomyces sp. are purified by recrystallising 3 times from hot glass-distilled MeOH, and the white crystals are dissolved in 25% aqueous MeOH and separated on a Partisil ODS-10_ column (9.4 x 25 cm) [Magnum-9 Whatman] using a 260nm detector. The column is eluted with MeOH/H2O mixture adjusted to 1:4 (v/v) then to 2:4 (v/v). The individual components are recovered and lyophilised. Ten components have been isolated, and all were active (to varying extents) depending on the lengths of the aliphatic side-chains. The mixture has UV max at 205 and 260nm (A 1cm 230 and 110). It is stable in H2O at neutral pH but unstable in acidic solution. It inhibits protein glycosylation. [Mahoney & Duskin J Biol Chem 254 6572 1979, Elnein Trends Biochem Sci 6 219 1981, Takatsuki J Antibiot 24 215 1971.] Uracil, uridine and uridine nucleotides. These are resolved by ion-exchange chromatography with AG1 (Cl form). [Lindsay et al. Anal Biochem 24 506 1968.]

References

1) Langan?et al. (1991),?Isoprenoids and astroglial cell cycling: diminished mevalonate availability and inhibition of dolichol-linked glycoprotein synthesis arrest cycling through distinct mechanisms;? J. Cell Physiol.,?149?284 2) Ding?et al. (2007),?Differential effects of endoplasmic reticulum stress-induced autophagy on cell survival;? J. Biol. Chem.,?282?4702 3) Jiang?et al. (2007),?Tunicamycin sensitizes human melanoma cells to tumor necrosis factor-related apoptosis inducing ligand-induced apoptosis by up-regulation of TRAIL-R2 via the unfolded protein response; Cancer Res.,?67?5880 4) Ishii?et al. (1987),?Dolichol-linked glycoprotein synthesis in G1 is necessary for DNA synthesis in synchronized primary cultures of cerebral glia;? J. Neurochem.,?49?1606

TUNICAMYCIN Preparation Products And Raw materials

Raw materials

Preparation Products

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TUNICAMYCIN Suppliers

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View Lastest Price from TUNICAMYCIN manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: TUNICAMYCIN 11089-65-9
Price: US $1.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-11

Hebei Mojin Biotechnology Co., Ltd

Product: TUNICAMYCIN 11089-65-9
Price: US $100.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 5000KG
Release date: 2023-09-05

Zhuozhou Wenxi import and Export Co., Ltd

Product: tunicamycin 11089-65-9
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-26

11089-65-9, TUNICAMYCINRelated Search:

10-AMINO-1-DECANOL ACETALDEHYDE DI-N-HEXYL ACETAL 8-DIMETHYLAMINO-1-OCTANOL TUNICAMYCIN 1,10-DIAMINODECANE 3-Acryloylamino-1-propanol solution, 50% in water DIPENTOXYETHANE 1,2,7,8-OCTANETETROL N-(2-Hydroxyethyl)acrylamide, HEAA N-DECYL ACRYLAMIDE 1,5-BIS(METHYLAMINO)-3-OXAPENTANE, 98 TUNICAMYCIN C1),TUNICAMYCIN B COMPLEX,tunicamycin C1 homolog TETRAHYDRO-2H-PYRAN-2-ETHANOL TUNICAMYCIN A1 HOMOLOG,tunicamycin A1 tunicamycin B3 TUNICAMYCIN UN3172 (III) 10 MG TUNICAMYCIN FROMSTEPTOMYCES CHARTREUSIS reducing agent and tunicamycin-responsive protein

Aids010655

Aids-010655

Nsc177382

TunicaMycin froM StreptoMyces lysosuperficus

TunicaMycin coMplex

InSolution? Tunicamycin,

TUNICAMYCIN, STREPTOMYCES IYSOSUPERFICUS

TUNICAMYCIN, STREPTOMYCES LYSOSUPERFICUS

TUNICAMYCIN

tunicamycin from A streptomyces species

tunicamycin from streptomyces lysosuperificus

Tunicamycin Streptomyces sp.

TUNICAMYCIN FROM STREPTOMYCES LYSOSUPERFIUS NOV. SP.

Tunicamycin from Streptomyces chartreusis

tunicamycin from streptomyces sp.

Tunicamycin (n= 8,9,10,11)

InSolution Tunicamycin, Streptomyces lysosuperficus - CAS 11089-65-9 - Calbiochem

TUNICAMYCIN USP/EP/BP

Tunicamycin Mixture

N-linked,DNA,UDP-HexNAc,inhibit,anti-cancer,Inhibitor,ATF6,synthesis,Influenza Virus,invasion,XBP-1,Bacterial,Fungal,glycoprotein,Tunicamycin,Antibiotic

isamycin

11089-65-9

C25H38N4O16

C39H64N4O16tunicamycinCn10

BioChemical

Antibiotics T-Z

Antibiotics

Antibiotics A to Z

NucleosidesMore...Close...

antibiotic

Antibacterial

Antibiotics

Antibiotics A to

Antibiotics by Application

Antibiotics T-ZAntibiotics

AntifungalAntibiotics

Antineoplastic and Immunosuppressive AntibioticsAntibiotics

AntiviralAntibiotics

Chemical Structure Class

Interferes with Protein SynthesisSpectrum of Activity

L - ZAntibiotics

Mechanism of Action

Spectrum of Activity

Signalling