11089-65-9 Usage
Description
Tunicamycin is 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 acid linked to the amino group of the tunicamine. The homologues vary in the composition of the fatty acid moiety. Tunicamycin is a white solid and possesses antimicrobial properties against Gram-positive bacteria, fungi, and viruses.
Uses
1. Used in Antiviral Applications:
Tunicamycin is used as an antiviral agent due to its ability to inhibit glycoprotein biosynthesis, including virus membrane glycoproteins.
2. Used in Studying Glycoproteins:
Tunicamycin is used as a tool in studying glycoproteins in a wide variety of biological systems. It is particularly useful in the study of glycoprotein synthesis, as it acts as an inhibitor of the transfer of saccharide moieties to dolichol during dolichol-linked glycoprotein synthesis.
3. Used in Cell Cycle Research:
Tunicamycin is used to prevent cell cycle progression in primary cultures of rat glial cells, as well as to inhibit lipid-mediated protein glycosylation in chick or mouse fibroblasts in a dose-dependent manner.
4. Used in Cancer Research:
Tunicamycin sensitizes EGFR inhibitor-resistant U251 glioma and Bx/PC-3 pancreatic adenocarcinoma cells to irradiation, making it a potential tool in cancer research and treatment.
5. Used in Drug Development:
Tunicamycin's ability to inhibit the N-acetylhexosamine (HexNAc) phosphotransferase family of enzymes in bacteria and prevent peptidoglycan biosynthesis, as well as its inhibition of N-acetylglucosamine (GlcNAc) phosphotransferase (GPT) in eukaryotes, makes it a valuable compound in the development of new drugs targeting various diseases, including infections and cancer.
Biochem/physiol Actions
Cell permeable: yes
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
Check Digit Verification of cas no
The CAS Registry Mumber 11089-65-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,1,0,8 and 9 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 11089-65:
(7*1)+(6*1)+(5*0)+(4*8)+(3*9)+(2*6)+(1*5)=89
89 % 10 = 9
So 11089-65-9 is a valid CAS Registry Number.
InChI:InChI=1/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
