基本情報
- CAS
67-99-2- 標準SMILES
CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3- InChIKey
FIVPIPIDMRVLAY-RBJBARPLSA-N- 分子式
- C13H14N2O4S2
- 平均分子量
- 326.4 g/mol
- 単同位体質量
- 326.03949928
概要
Gliotoxin is a pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. It has a role as a mycotoxin, an immunosuppressive agent, an antifungal agent, a proteasome inhibitor and an EC 2.5.1.58 (protein farnesyltransferase) inhibitor. It is an organic disulfide, an organic heterotetracyclic compound, a dipeptide and a pyrazinoindole.
名称と識別子
- 優先名称
- Gliotoxin
- IUPAC
- (1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione
- 現地名
- (3R)-2-メチル-3-(ヒドロキシメチル)-6β-ヒドロキシ-3α,10aα-エピジチオ-1,2,3,4,5aβ,6,10,10a-オクタヒドロピラジノ[1,2-a]インドール-1,4-ジオン
- 英語名
- GLIOTOXIN
- 分子式
- C13H14N2O4S2
- 分子量
- 326.39
名称と別名
gliotoxin67-99-2AspergillinDTXSID608771795L648PH06KCHEBI:5385NSC-10286610H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-GliotoxinsS. N.-12870(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dioneNSC102866
名称をさらに表示
2,3,5aβ,6-テトラヒドロ-6β-ヒドロキシ-3β-(ヒドロキシメチル)-2-メチル-10H-3α,10aα-エピジチオピラジノ[1,2-a]インドール-1,4-ジオングリオトキシンアスペルギリン(3R)-2-メチル-3-(ヒドロキシメチル)-6β-ヒドロキシ-3α,10aα-エピジチオ-1,2,3,4,5aβ,6,10,10a-オクタヒドロピラジノ[1,2-a]インドール-1,4-ジオン抗菌グリオトキシン 100ΜG/MLグリオトキシン FROM GLIOCLADIUM FIMBRIATUM(1R,7S,8S,11R)-7-ヒドロキシ-11-(ヒドロキシメチル)-15-メチル-12,13-ジチア-9,15-ジアザテトラシクロ[9.2.2.01,9.03,8]ペンタデカ-3,5-ジエン-10,14-ジオン(3R,5aS,6S,10aR)-2,3,5a,6-テトラヒドロ-6-ヒドロキシ-3-(ヒドロキシメチル)-2-メチル-10H-3α,10a-エピジチオピラジノ[1,2-a]インドール-1,4-ジオン(3R,5aS,6S,10aR)-2-メチル-3-(ヒドロキシメチル)-6-ヒドロキシ-3,10a-エピジチオ-1,2,3,4,5a,6,10,10a-オクタヒドロピラジノ[1,2-a]インドール-1,4-ジオン
物性
構造計算による物性
- XLogP
- -0.7
- 極性表面積
- 132 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 6
- 回転可能結合数
- 1
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 621
実験および物理化学的性質
DrugsPharmaceuticals -> Antibiotics
物理化学的性質
- 融点
- 221 °C · 221°C (rough estimate)
- 沸点
- 699.7 · 699.7±55.0 °C(Predicted)
- 比旋光度
- 25 · D25 -290° (c = 0.08 in ethanol)
- 比重(密度)
- 1.4069 · 1.4069 (rough estimate)
- 屈折率
- 1.651 · 1.6510 (estimate)
- 闪点
- 2 ℃ · 2℃
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 10 mg/mL · クロロホルム：10 mg/mL 無色透明
- 外見
- 白い固体
- 酸解離定数(Pka)
- 12.9 · 12.90±0.40(Predicted)
- 色
- MeOHからの単斜晶系結晶
- Merck
- 13 · 13,4454
- BRN
- 50675 · 50675
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 1 か月間保存できます。
- InChI
- InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
- InChIKey
- FIVPIPIDMRVLAY-RBJBARPLSA-N
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information10H-3,10a-Epidithiopyrazino1,2-aindole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-, (3R,5aS,6S,10aR)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (100%)
毒性情報
Health EffectsGliotoxin has immunosuppressive effects. It is also cytotoxic and causes neurite degeneration. (L1941, A2951)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. It also acts as an inhibitor of farnesyl transferase. Gliotoxin noncompetitively inhibits the chymotrypsin-like activity of the 20S proteasome and displays anti-inflammatory activity. It acts by blocking thiol groups in the cell membranes. Gliotoxin is also cytotoxic and causes neurite degeneration. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (L1941, A2951, A3014)
化学と産業
薬理情報
MeSH Pharmacological Classification
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
用途と製造
Uses
Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Gliotoxin possesses immunosuppressive properties. (L1941)
応用分野
使用Gliotoxin is a sulfur-containing mycotoxin produced by species of fungi and pathogens of humans. Gliotoxin exhibits inhibitory activities against histone H3K9 methyltransferase, a key enzyme in the re gulation of transcriptional activity by writing epigenetic marks. Gliotoxin also exhibits immunosuppressive properties by causing apoptosis of cells of the immune system. In addition, various studies suggests Gliotoxin may also be a potential anti-inflammatory, antibiotic, antifungal and antiviral agent.
調製方法
純化方法Purify gliotoxin by recrystallisation from MeOH. Its solubility in CHCl3 is 1%. The dibenzoyl derivative has m 202o (from CHCl3/MeOH). [Glister & Williams Nature 153 651 1944, Elvidge & Spring J Chem Soc Suppl 135 1949, Johnson et al. J Am Chem Soc 65 2005 1943, Bracken & Raistrick Biochem J 41 569 1947.]
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