T7765

衣霉素 来源于链霉菌 属

• CAS号: 11089-65-9
• Beilstein: 6888090
• MDL號碼: MFCD00065709
• 分類程式碼代碼: 12352200
• PubChem物質ID: 57654701
• NACRES: NA.77

属性

• 品質等級: 300
• 溶解度: 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
• 抗生素活性譜: fungi; viruses
• 作用方式: protein synthesis | interferes
• 儲存溫度: 2-8°C
• SMILES 字串: 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 密鑰: YJQCOFNZVFGCAF-WPTOCQRYSA-N

说明

一般說明

包含同系物A、B、C和D。成分可能因批次而异。标识在标签上的实际含量。

化学结构：核苷

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.

應用

衣霉素已被用于在HeLa细胞中研究人质子偶联叶酸转运蛋白（HsPCFT）的N联糖基化作用。衣霉素还被用于在COS-7细胞中研究柯萨奇病毒和腺病毒受体（CAR）糖基化的功能作用。

生化／生理作用

阻断蛋白质N-糖苷键的形成。

準備報告

衣霉素可以4.9-5.1 mg/ml溶于DMSO并产生一种透明至略微有点浑浊、无色至黄色的溶液。此外，衣霉素还可溶于DMF（>10 mg/ml）、吡啶（>10 mg/ml）、水（<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，最好是>8。衣霉素即使通过加热也不会溶于pH 8的磷酸盐缓冲液以形成1 mg/ml的浓度，但可通过将pH升高至9并重新滴定至pH 7-8来实现溶解性。

安全信息

• 象形圖: GHS06
• 訊號詞: Danger
• 危險聲明: H300
• 防範說明: P264 - P270 - P301 + P310 - P405 - P501
• 危險分類: Acute Tox. 1 Oral
• 儲存類別代碼: 6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
• 水污染物質分類（WGK）: WGK 3
• 閃點（°F）: Not applicable
• 閃點（°C）: Not applicable
• 個人防護裝備: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges