Tunicamycin | CAS#11089-65-9

MedKoo Cat#: 462648 | Name: Tunicamycin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tunicamycin, a mixture of nucleoside antibiotics, is a specific inhibitor of N-linked glycoslylation that blocks the first step of glycoprotein synthesis thereby inducing protein unfolding. Tunicamycin impairs ALK phosphorylation and disrupts pro-survival signaling and cell viability in various neuroblastoma cell lines. Tunicamycin can also inhibit protein palmitoylation.

Chemical Structure

Tunicamycin

CAS#11089-65-9

Theoretical Analysis

MedKoo Cat#: 462648

Name: Tunicamycin

CAS#: 11089-65-9

Chemical Formula: C30H46N4O16

Exact Mass: 718.2909

Molecular Weight: 718.71

Elemental Analysis: C, 50.14; H, 6.45; N, 7.80; O, 35.62

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

NSC 177382; NSC177382; NSC-177382;

IUPAC/Chemical Name

(E)-N-((2S,3R,4R,5R,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(2-((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)-5-methylhex-2-enamide

InChi Key

ZHSGGJXRNHWHRS-VIDYELAYSA-N

InChi Code

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

SMILES Code

CC(C/C=C/C(N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@H]2O[C@@H]([C@H]([C@@H]([C@H]2NC(C)=O)O)O)CO)CC([C@H]3O[C@@H](N4C=CC(NC4=O)=O)[C@@H]([C@@H]3O)O)O)O)O)=O)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 718.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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Endoplasmic reticulum stress induced by tunicamycin and thapsigargin protects against transient ischemic brain injury: Involvement of PARK2-dependent mitophagy. Autophagy. 2014 Oct 1;10(10):1801-13. doi: 10.4161/auto.32136. Epub 2014 Aug 5. PMID: 25126734; PMCID: PMC4198364. 5: Zhang S, Gui C, Shao M, Kumar PS, Huang H, Ju J. Antimicrobial tunicamycin derivatives from the deep sea-derived Streptomyces xinghaiensis SCSIO S15077. Nat Prod Res. 2020 Jun;34(11):1499-1504. doi: 10.1080/14786419.2018.1493736. Epub 2018 Nov 16. PMID: 30445836. 6: Feng B, Huang X, Jiang D, Hua L, Zhuo Y, Wu D. Endoplasmic Reticulum Stress Inducer Tunicamycin Alters Hepatic Energy Homeostasis in Mice. Int J Mol Sci. 2017 Aug 4;18(8):1710. doi: 10.3390/ijms18081710. PMID: 28777337; PMCID: PMC5578100. 7: Rapino C, Castellucci A, Lizzi AR, Sabatucci A, Angelucci CB, Tortolani D, Rossi G, D'Andrea G, Maccarrone M. Modulation of Endocannabinoid-Binding Receptors in Human Neuroblastoma Cells by Tunicamycin. Molecules. 2019 Apr 11;24(7):1432. doi: 10.3390/molecules24071432. PMID: 30979007; PMCID: PMC6479803. 8: Yabuki Y, Ikeda A, Araki M, Kajiwara K, Mizuta K, Funato K. Sphingolipid/Pkh1/2-TORC1/Sch9 Signaling Regulates Ribosome Biogenesis in Tunicamycin-Induced Stress Response in Yeast. Genetics. 2019 May;212(1):175-186. doi: 10.1534/genetics.118.301874. Epub 2019 Mar 1. PMID: 30824472; PMCID: PMC6499531. 9: Cırrık S, Hacioglu G, Ayyıldız SN, Tezcan B, Abidin İ, Aydın-Abidin S, Noyan T. Renal response to tunicamycin-induced endoplasmic reticulum stress in BDNF heterozygous mice. Adv Clin Exp Med. 2019 Sep;28(9):1161-1170. doi: 10.17219/acem/100647. PMID: 31430074. 10: Yamamoto K, Katsuyama A, Ichikawa S. Structural requirement of tunicamycin V for MraY inhibition. Bioorg Med Chem. 2019 Apr 15;27(8):1714-1719. doi: 10.1016/j.bmc.2019.02.035. Epub 2019 Mar 2. PMID: 30850266. 11: Xiao H, Smeekens JM, Wu R. Quantification of tunicamycin-induced protein expression and N-glycosylation changes in yeast. Analyst. 2016 Jun 21;141(12):3737-45. doi: 10.1039/c6an00144k. Epub 2016 Mar 23. PMID: 27007503. 12: Price NP, Jackson MA, Vermillion KE, Blackburn JA, Li J, Yu B. Selective catalytic hydrogenation of the N-acyl and uridyl double bonds in the tunicamycin family of protein N-glycosylation inhibitors. J Antibiot (Tokyo). 2017 Dec;70(12):1122-1128. doi: 10.1038/ja.2017.141. Epub 2017 Nov 1. PMID: 29089601. 13: Bik E , Mielniczek N , Jarosz M , Denbigh J , Budzynska R , Baranska M , Majzner K . Tunicamycin induced endoplasmic reticulum changes in endothelial cells investigated in vitro by confocal Raman imaging. Analyst. 2019 Nov 4;144(22):6561-6569. doi: 10.1039/c9an01456j. PMID: 31576836. 14: Hakulinen JK, Hering J, Brändén G, Chen H, Snijder A, Ek M, Johansson P. MraY-antibiotic complex reveals details of tunicamycin mode of action. Nat Chem Biol. 2017 Mar;13(3):265-267. doi: 10.1038/nchembio.2270. Epub 2017 Jan 9. PMID: 28068312. 15: Price NPJ, Jackson MA, Singh V, Hartman TM, Blackburn JA, Dowd PF. Synergistic enhancement of beta-lactam antibiotics by modified tunicamycin analogs TunR1 and TunR2. J Antibiot (Tokyo). 2019 Nov;72(11):807-815. doi: 10.1038/s41429-019-0220-x. Epub 2019 Aug 16. PMID: 31420587. 16: Gabani BB, Sulochana SP, Kiran V, Todmal U, Mullangi R. Validated LC-ESI- MS/MS method for the determination of tunicamycin in rat plasma: Application to a pharmacokinetic study. Biomed Chromatogr. 2019 Nov;33(11):e4661. doi: 10.1002/bmc.4661. Epub 2019 Sep 1. PMID: 31325183. 17: Chen W, Qu D, Zhai L, Tao M, Wang Y, Lin S, Price NP, Deng Z. Characterization of the tunicamycin gene cluster unveiling unique steps involved in its biosynthesis. Protein Cell. 2010 Dec;1(12):1093-105. doi: 10.1007/s13238-010-0127-6. Epub 2010 Dec 9. PMID: 21153459; PMCID: PMC4875072. 18: Han X, Zhang X, Li H, Huang S, Zhang S, Wang F, Shi Y. Tunicamycin enhances the antitumor activity of trastuzumab on breast cancer in vitro and in vivo. Oncotarget. 2015 Nov 17;6(36):38912-25. doi: 10.18632/oncotarget.5334. PMID: 26498681; PMCID: PMC4770746. 19: Dong YY, Wang H, Pike ACW, Cochrane SA, Hamedzadeh S, Wyszyński FJ, Bushell SR, Royer SF, Widdick DA, Sajid A, Boshoff HI, Park Y, Lucas R, Liu WM, Lee SS, Machida T, Minall L, Mehmood S, Belaya K, Liu WW, Chu A, Shrestha L, Mukhopadhyay SMM, Strain-Damerell C, Chalk R, Burgess-Brown NA, Bibb MJ, Barry Iii CE, Robinson CV, Beeson D, Davis BG, Carpenter EP. Structures of DPAGT1 Explain Glycosylation Disease Mechanisms and Advance TB Antibiotic Design. Cell. 2018 Nov 1;175(4):1045-1058.e16. doi: 10.1016/j.cell.2018.10.037. PMID: 30388443; PMCID: PMC6218659. 20: Price NP, Labeda DP, Naumann TA, Vermillion KE, Bowman MJ, Berhow MA, Metcalf WW, Bischoff KM. Quinovosamycins: new tunicamycin-type antibiotics in which the α, β-1″,11'-linked N-acetylglucosamine residue is replaced by N-acetylquinovosamine. J Antibiot (Tokyo). 2016 Aug;69(8):637-46. doi: 10.1038/ja.2016.49. Epub 2016 May 18. PMID: 27189123.