SML1287

Tunicamycin

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

• Empirical Formula (Hill Notation): C₃₇H₆₀N₄O₁₆
• CAS Number: 11089-65-9
• Molecular Weight: 816.89
• UNSPSC Code: 51111800
• NACRES: NA.77
• EC Number: 200-664-3
• Form: DMSO solution

Properties

• Product Name: Tunicamycin Ready Made Solution, 5 mg/mL in DMSO, from Streptomyces sp.
• biological source: Streptomyces sp.
• Quality Segment: 200
• form: DMSO solution
• concentration: 5 mg/mL in DMSO
• storage temp.: 2-8°C
• SMILES string: N4(C=CC(=O)NC4=O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(O)C[C@H]2O[C@@H]([C@@H]([C@H]([C@H]2O)O)NC(=O)\C=C\CC(C)C)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3NC(=O)C)O)O)CO
• InChI: 1S/C30H46N4O16/c1-11(2)5-4-6-16(38)32-19-23(43)20(40)14(47-29(19)50-28-18(31-12(3)36)22(42)21(41)15(10-35)48-28)9-13(37)26-24(44)25(45)27(49-26)34-8-7-17(39)33-30(34)46/h4,6-8,11,13-15,18-29,35,37,40-45H,5,9-10H2,1-3H3,(H,31,36)(H,32,38)(H,33,39,46)/b6-4+/t13?,14-,15-,18-,19-,20+,21-,22-,23-,24+,25-,26-,27-,28-,29-/m1/s1
• InChI key: ZHSGGJXRNHWHRS-PEALBESXSA-N

Description

General description

Tunicamycin Ready Made Solution contains homologues A,B,C, and D. The composition may vary from lot to lot. Actual content given on label.

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

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.

Biochem/physiol Actions

Tunicamycin is an antibacterial and antifungal.

Tunicamycin is an antibacterial and antifungal. Tunicamycin blocks the formation of protein N-glycosidic linkages by inhibiting the transfer of N-acetylglucosamine 1-phosphate to dolichol monophosphate. Tunicamycin inhibits bacterial and eukaryote N-acetylglucosamine transferases and prevents formation of N-acetylglucosamine lipid intermediates.

Tunicamycin plays an important role in the antitumor activity of trastuzumab on breast cancer in vitro and in vivo. In human cell lines, tunicamycin enhances cytotoxicity stimulated by cisplatin. It prevents angiogenesis in nude mice by reducing the expression of vascular endothelial growth factor (VEGF).

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk: WGK 1
• flash_point_f: 188.6 °F
• flash_point_c: 87 °C