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TUNICAMYCIN

TUNICAMYCIN Structure
TUNICAMYCIN
  • CAS No.11089-65-9
  • Chemical Name:TUNICAMYCIN
  • CBNumber:CB4211576
  • Molecular Formula:C37H60N4O16
  • Formula Weight:816.89
  • MOL File:11089-65-9.mol
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
  • biological source Streptomyces sp.
  • 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
  • EWG's Food Scores 1
  • FDA UNII 55W4525Q2E
  • EPA Substance Registry System Tunicamycin (11089-65-9)
  • UNSPSC Code 51111800
  • NACRES NA.77
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
  • NFPA 704:
    0
    4 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H300
  • Precautionary statements P264-P270-P301+P310-P405-P501
TUNICAMYCIN Price More Price(7)
  • Brand: Sigma-Aldrich(India)
  • Product number: T7765
  • Product name : Tunicamycin from Streptomyces sp.
  • Purity: 
  • Packaging: 1MG
  • Price: ₹5585.7
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: T7765
  • Product name : Tunicamycin from Streptomyces sp.
  • Purity: 
  • Packaging: 5MG
  • Price: ₹17341.65
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: T7765
  • Product name : Tunicamycin from Streptomyces sp.
  • Purity: 
  • Packaging: 10MG
  • Price: ₹31706.43
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: T7765
  • Product name : Tunicamycin from Streptomyces sp.
  • Purity: 
  • Packaging: 50MG
  • Price: ₹93343.98
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: 654380
  • Product name : Tunicamycin, Streptomyces lysosuperficus - CAS 11089-65-9 - Calbiochem
  • Purity: Tunicamycin, Streptomyces lysosuperficus, CAS 11089-65-9, is a nucleoside antibiotic that inhibits N-linked glycosylation and blocks the formation of
  • Packaging: 10MG
  • Price: ₹23150
  • Updated: 2022/06/14
  • Buy: Buy

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 As a tool in studying glycoproteins in a wide variety of biological systems.
  • 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.
  • 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
TUNICAMYCIN Suppliers
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    BOC Sciences
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    TargetMol Chemicals Inc.
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TUNICAMYCIN Spectrum
11089-65-9, TUNICAMYCINRelated Search:
  • Signalling
  • Spectrum of Activity
  • Mechanism of Action
  • L - ZAntibiotics
  • Interferes with Protein SynthesisSpectrum of Activity
  • Chemical Structure Class
  • AntiviralAntibiotics
  • Antineoplastic and Immunosuppressive AntibioticsAntibiotics
  • AntifungalAntibiotics
  • Antibiotics T-ZAntibiotics
  • Antibiotics by Application
  • Antibiotics A to
  • Antibiotics
  • Antibacterial
  • antibiotic
  • NucleosidesMore...Close...
  • 抑制剂
  • 原料药
  • 小分子
  • 试剂盒-细胞分析试剂盒
  • 化工原料
  • 化合物
  • 对照品
  • 生化试剂
  • 抗生素、生物碱
  • 抗生素及抗病毒
  • 抗生素
  • 细胞生物学
  • 细胞信号和神经生物学
  • 微生物代谢物
  • Antibiotics A to Z
  • Antibiotics
  • Antibiotics T-Z
  • BioChemical
  • C39H64N4O16tunicamycinCn10
  • C25H38N4O16
  • TUNICAMYCIN FROM STREPTOMYCES LYSOSUPERFICUS 衣霉素 | CAS 11089-65-9
  • TUNICAMYCIN,蛋白GLYCOSYLATION抑制剂
  • 衣霉素(混合物)
  • TUNICAMYCIN游离态
  • 衣霉素(N-连接的糖基化抑制剂)
  • 衣霉素来源于链霉菌
  • 衣霉素,来源于溶血链球菌
  • 衣霉素(链霉菌属)
  • TUNICAMYCIN FROM STREPTOMYCES SP. 来源于链霉菌 属
  • 衣霉素 来源于链霉菌属
  • 链病毒菌素
  • 源于STREPTOMYCESLYSOSUPERFIUSNOV.SP.的链病毒菌素
  • 衣霉素
  • TUNICAMYCIN 衣霉素
  • 衣霉素复合物
  • 11089-65-9
  • Tunicamycin, <i>Streptomyces lysosuperficus</i>
  • Tunicamycin, Protein glycosylation inhibitor
  • isamycin
  • N-linked,DNA,UDP-HexNAc,inhibit,anti-cancer,Inhibitor,ATF6,synthesis,Influenza Virus,invasion,XBP-1,Bacterial,Fungal,glycoprotein,Tunicamycin,Antibiotic
  • Tunicamycin Mixture
  • TUNICAMYCIN USP/EP/BP

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