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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/09/04 17:23:45」(JST)

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Tunicamycin is a mixture of homologous nucleoside antibiotics that inhibits the UDP-HexNAc: polyprenol-P HexNAc-1-P family of enzymes. In eukaryotes, this includes the enzyme GlcNAc phosphotransferase (GPT), which catalyzes the transfer of N-actelyglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichol phosphate in the first step of glycoprotein synthesis. Tunicamycin blocks the synthesis of all N-linked glycoproteins (N-glycans) and causes cell cycle arrest in G1 phase. It is used as an experimental tool in biology, e.g. to induce unfolded protein response.^[1] Tunicamycin is produced by several bacteria, including Streptomyces clavuligerus and Streptomyces Iysosuperficus.

Tunicamycin homologues have varying molecular weights owing to the variability in fatty acids side chain conjugates.^[2]

References[edit source | edit]

^ Hepatitis C virus envelope proteins regulate CHOP via induction of ...
^ [1] Tunicamycin product details]

External links[edit source | edit]

Book section of Essentials in Glycobiology (1999) Tunicamycin: Inhibition of DOL-PP-GlcNAc Assembly
Tunicamycin data sheet prepared by a student of the Open University, UK

English Journal

IDH1, a CHOP and C/EBPβ-responsive gene under ER stress, sensitizes human melanoma cells to hypoxia-induced apoptosis.

Yang X1, Du T1, Wang X1, Zhang Y1, Hu W2, Du X1, Miao L3, Han C4.
Cancer letters.Cancer Lett.2015 Sep 1;365(2):201-10. doi: 10.1016/j.canlet.2015.05.027. Epub 2015 Jun 3.
Isocitrate dehydrogenase1 (IDH1) is of great importance in cell metabolism and energy conversion. However, alterations in IDH1 in response to stress and excise-regulated mechanisms are not well described. Here we investigated gene expression profiles under ER stress in melanoma cells and found that
PMID 26049021

Tunicamycin promotes apoptosis in leukemia cells through ROS generation and downregulation of survivin expression.

Lim EJ1, Heo J, Kim YH.
Apoptosis : an international journal on programmed cell death.Apoptosis.2015 Aug;20(8):1087-98. doi: 10.1007/s10495-015-1135-z.
Tunicamycin (TN), one of the endoplasmic reticulum stress inducers, has been reported to inhibit tumor cell growth and exhibit anticarcinogenic activity. However, the mechanism by which TN initiates apoptosis remains poorly understood. In the present study, we investigated the effect of TN on the ap
PMID 26022098

The glutathione mimic ebselen inhibits oxidative stress but not endoplasmic reticulum stress in endothelial cells.

Ahwach SM1, Thomas M1, Onstead-Haas L1, Mooradian AD1, Haas MJ2.
Life sciences.Life Sci.2015 Aug 1;134:9-15. doi: 10.1016/j.lfs.2015.05.004. Epub 2015 May 23.
AIMS: Reactive oxygen species are associated with cardiovascular disease, diabetes, and atherosclerosis, yet the use of antioxidants in clinical trials has been ineffective at improving outcomes. In endothelial cells, high-dextrose-induced oxidative stress and endoplasmic reticulum stress promote en
PMID 26006036

Japanese Journal

Bovine milk phospholipid fraction protects Neuro2a cells from endoplasmic reticulum stress via PKC activation and autophagy(MEDICAL BIOTECHNOLOGY)

Nagai Kaoru
Journal of bioscience and bioengineering 114(4), 466-471, 2012-10-00
… Neuro2a cells were induced cell death by ER stressor tunicamycin (TM) or thapsigargin (TG), and studied whether mPL could attenuate the toxicity. …
NAID 110009543736

神経分化制御におけるツニカマイシン誘導性小胞体ストレスの影響

川田浩一,藤永直己,山下美穂,佐藤亜紗美,東野俊作,金子雅幸,野村靖幸,大熊康修
日本神経精神薬理学雑誌 = Japanese journal of psychopharmacology 32(2), 115-116, 2012-04-25
NAID 10030657002

Role of the plant-specific endoplasmic reticulum stress-inducible gene T1N1 in the formation of pollen surface structure in Arabidopsis thaliana

Iwata Yuji,Nishino Tsuneyo,Iwano Megumi [他],TAKAYAMA Seiji,KOIZUMI Nozomu
Plant biotechnology 29(1), 51-56, 2012-03-25
… We have identified tunicamycin induced 1 (TIN1), a plant-specific ER stress-inducible Arabidopsis thaliana gene. …
NAID 10030561397

Related Pictures

★リンクテーブル★

リンク元	「ツニカマイシン」「チュニカマイシン」

「ツニカマイシン」

Tunicamycin
	IUPAC name (E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)- 3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy- 6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)- 3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan- 3-yl]-5-methylhex-2-enamide
	Other names NSC 177382
Identifiers
CAS number	11089-65-9
PubChem	6433557
MeSH	Tunicamycin
ChEMBL	CHEMBL505513
Jmol-3D images	{{#if:CC(C)C\C=C\C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)CC([C@@H]3[C@H]([C@H] ([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O\|Image 1
	SMILES CC(C)C\C=C\C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)CC([C@@H]3[C@H]([C@H] ([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O ;
Properties
Molecular formula	C39H64N4O16
Molar mass	N/A
Hazards
R-phrases	28
S-phrases	28-37/39-45
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references