T7765

Tunicamycin

from Streptomyces sp., ≥98% (HPLC), powder, N-acetylglucosamine transferase inhibitor

• CAS Number: 11089-65-9
• Beilstein: 6888090
• MDL number: MFCD00065709
• UNSPSC Code: 51111800
• PubChem Substance ID: 57654701
• NACRES: NA.77

Properties

• product name: Tunicamycin from Streptomyces sp.,
• Quality Level: 300
• solubility: 95% ethanol: soluble 1 mg/mL, clear to faintly hazy; THF: soluble <1 mg/mL; dioxane: soluble <1 mg/mL; DMF: soluble >10 mg/mL; pyridine: >10 mg/mL; DMSO: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow; methanol: slightly soluble 4.9-5.1 mg/mL; methanol: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow; acetone: insoluble; aqueous base: insoluble; chloroform: insoluble; ethyl acetate: insoluble
• antibiotic activity spectrum: fungi; viruses
• Mode of action: protein synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: CC(C)CCCCCCCC\C=C\C(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)O[C@H]1O[C@@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4NC(C)=O
• InChI: 1S/C37H60N4O16/c1-18(2)12-10-8-6-4-5-7-9-11-13-23(45)39-26-30(50)27(47)21(54-36(26)57-35-25(38-19(3)43)29(49)28(48)22(17-42)55-35)16-20(44)33-31(51)32(52)34(56-33)41-15-14-24(46)40-37(41)53/h11,13-15,18,20-22,25-36,42,44,47-52H,4-10,12,16-17H2,1-3H3,(H,38,43)(H,39,45)(H,40,46,53)/b13-11+/t20-,21-,22+,25+,26-,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+/m1/s1
• InChI key: YJQCOFNZVFGCAF-WPTOCQRYSA-N

Description

General description

Chemical structure: nucleoside

Contains homologues A,B,C, and D. Composition may vary from lot to lot. Actual content given on label.

Tunicamycin is an antibiotic and a glycosylation inhibitor. Its mode of action includes blocking human UDP-HexNAc:polyprenol-P HexNAc-1-P enzymes in the enzyme GlcNAc phosphotransferase (GPT). Glycosylation is a major post-translational modification that plays a critical role in glycoprotein folding, stability, and subcellular localization, as well as in the biological functions of the glycoprotein. Abnormal glycosylation has been identified as a signature of cancer and has been shown to play a significant role in tumor progression, metastasis, and chemoresistance. Research shows tunicamycin exhibits antitumor action. Furthermore, tunicamycin inhibition of N-glycosylation ultimately results in the build-up of unstructured proteins in the endoplasmic reticulum (ER) lumen, potentially leading to ER stress. Tunicamycin also exhibits antibacterial and antifungal actions. It blocks the formation of protein N-glycosidic linkages by inhibiting the transfer of N-acetylglucosamine 1-phosphate to dolichol monophosphate. Tunicamycin also Inhibits bacterial and eukaryote N-acetylglucosamine transferases and prevents the formation of N-acetylglucosamine lipid intermediates.

Application

Tunicamycin has been used to study the effect of N-linked glycosylation of human proton-coupled folate transporter (HsPCFT) in HeLa cells. Tunicamycin has also been used to study the functional effects of coxsackievirus and adenovirus receptor (CAR) glycosylation in COS-7 cells. Tunicamycin from Streptomyces sp. has been used to inhibit N-glycosylation in cell culture experiments.

Biochem/physiol Actions

Blocks the formation of protein N-glycosidic linkages.

Preparation Note

Tunicamycin dissolves in DMSO at 4.9-5.1 mg/ml and yields a clear to very slightly hazy, colorless to yellow solution. Furthermore, tunicamycin is soluble in DMF (>10 mg/ml), pyridine (>10 mg/ml), water (<5 mg/ml, pH 9.0), dioxane (<1 mg/ml) and THF. However, it is insoluble in other organic solvents such as acetone, chloroform, and ethyl acetate, and in aqueous solutions with pH <6. Aqueous solutions can be prepared from stock solutions by diluting with water at pH 8-10 or with buffers with pH >7, preferably >8. Tunicamycin will not dissolve in phosphate buffer, pH 8, at 1 mg/ml, even with heating, but solubility can be achieved by raising the pH to 9 and back titrating to pH 7-8.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 1 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves