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SML1287

Sigma-Aldrich

Tunicamycin

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

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About This Item

Wzór empiryczny (zapis Hilla):
C37H60N4O16
Numer CAS:
11089-65-9
Masa cząsteczkowa:
816.89
Numer WE:
200-664-3
Kod UNSPSC:
51111800
NACRES:
NA.77

product name

Tunicamycin Ready Made Solution, 5 mg/mL in DMSO, from Streptomyces sp.

pochodzenie biologiczne

Streptomyces sp.

Poziom jakości

200

Postać

DMSO solution

stężenie

5 mg/mL in DMSO

temp. przechowywania

2-8°C

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

Klucz InChI

ZHSGGJXRNHWHRS-PEALBESXSA-N

Opis ogólny

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.

Zastosowanie

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.

Działania biochem./fizjol.

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).
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Kod klasy składowania

10 - Combustible liquids

Klasa zagrożenia wodnego (WGK)

WGK 1

Temperatura zapłonu (°F)

188.6 °F

Temperatura zapłonu (°C)

87 °C

Certyfikaty analizy (CoA)

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The specific site of tunicamycin inhibition in the formation of dolichol-bound N-acetylglucosamine derivatives.
L Lehle et al.
FEBS letters, 72(1), 167-170 (1976-11-15)
Tunicamycin enhances the antitumor activity of trastuzumab on breast cancer in vitro and in vivo.
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Oncotarget, 6(36), 38912?38925-38912?38925 (2015)
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Protein homeostasis in eukaryotic cells is regulated by 2 highly conserved degradative pathways, the ubiquitin-proteasome system (UPS) and macroautophagy/autophagy. Recent studies revealed a coordinated and complementary crosstalk between these systems that becomes critical under proteostatic stress. Under physiological conditions, however
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The enhancer of zeste homolog 2 (EZH2) is the main enzymatic subunit of the PRC2 complex, which catalyzes trimethylation of histone H3 lysine 27 (H3K27me3) to promote transcriptional silencing. EZH2 is overexpressed in multiple types of cancer including triple-negative breast
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