Aspergillin (Synonyms: グリオトキシン; Gliotoxin)

Name: Gliotoxin
Brand: MedChemExpress
SKU: HY-N6727
Rating: 5.0 (2 reviews)

製品番号: HY-N6727 純度: 99.50%: Data Sheet SDS COA 取扱説明書
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Gliotoxin is a secondary metabolite, the most abundant mycotoxin secreted by A. fumigatus, inhibits the phagocytosis of macrophages and the immune functions of other immune cells . Gliotoxin inhibits inducible NF-κB activity by preventing IκB degradation, which consequently induces host-cell apoptosis. Gliotoxin activates PKA and increases intracellular cAMP concentration; modulates actin cytoskeleton rearrangement to facilitate A. fumigatus internalization into lung epithelial cells. Gliotoxin is a potent NOTCH2 transactivation inhibitor, can effectively induce apoptosis of chronic lymphocytic leukemia (CLL) cells.

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Aspergillin 構造式

CAS 番号 : 67-99-2

容量	価格（税別）	在庫状況	数量
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO ready for reconstitution	USD 462	在庫あり	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in DMSO	USD 462	在庫あり	Estimated Time of Arrival: December 31
Solid
1 mg	$190	在庫あり	Estimated Time of Arrival: December 31
5 mg	$420	在庫あり	Estimated Time of Arrival: December 31
10 mg	$720	在庫あり	Estimated Time of Arrival: December 31
25 mg	$1450	在庫あり	Estimated Time of Arrival: December 31
50 mg		お問い合わせ
100 mg		お問い合わせ

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Based on 2 publication(s) in Google Scholar

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PKA PKAR PKACα

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NF-κB NF-κB1/p50 RelA/p65 RelB c-Rel

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Aminoglycoside Glycopeptide Lipopeptide Macrolide Oxazolidinone Quinolone Tetracycline β-lactam

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製品説明

Gliotoxin is a secondary metabolite, the most abundant mycotoxin secreted by A. fumigatus, inhibits the phagocytosis of macrophages and the immune functions of other immune cells ^[1]. Gliotoxin inhibits inducible NF-κB activity by preventing IκB degradation, which consequently induces host-cell apoptosis^[2]. Gliotoxin activates PKA and increases intracellular cAMP concentration; modulates actin cytoskeleton rearrangement to facilitate A. fumigatus internalization into lung epithelial cells^[3]. Gliotoxin is a potent NOTCH2 transactivation inhibitor, can effectively induce apoptosis of chronic lymphocytic leukemia (CLL) cells^[4].

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	0.003 μM Compound: 10	Cytotoxicity against human A549 cells Cytotoxicity against human A549 cells	[PMID: 20303767]
CCRF-CEM	IC₅₀	0.15 μM Compound: gliotoxin	Cytotoxicity against human CEM cells after 96 hrs Cytotoxicity against human CEM cells after 96 hrs	[PMID: 16124785]
HCT-116	IC₅₀	0.41 μM Compound: 311	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 38181652]
HCT-116	IC₅₀	1.24 μM Compound: 311	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay	[PMID: 38181652]
HEK293	IC₅₀	1.58 μM Compound: 311	Cytotoxicity against HEK293 cells assessed as cell growth inhibition Cytotoxicity against HEK293 cells assessed as cell growth inhibition	[PMID: 38181652]
HeLa	IC₅₀	2.45 μM Compound: 10	Cytotoxicity against human HeLa cells Cytotoxicity against human HeLa cells	[PMID: 20303767]
HepG2	IC₅₀	0.21 μM Compound: 311	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
HepG2	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
HUVEC	IC₅₀	0.123 μM Compound: 10	Cytotoxicity against HUVEC Cytotoxicity against HUVEC	[PMID: 20303767]
Jurkat	IC₅₀	<1 μM Compound: 10	Cytotoxicity against human Jurkat cells after 40 hrs bioluminescence assay Cytotoxicity against human Jurkat cells after 40 hrs bioluminescence assay	[PMID: 20303767]
Macrophage	ED₅₀	0.104 μM Compound: 10	Immunomodulatory activity in macrophage assessed as inhibition of phagocytosis Immunomodulatory activity in macrophage assessed as inhibition of phagocytosis	[PMID: 20303767]
MCF7	IC₅₀	0.08 μM Compound: 311	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
MCF7	IC₅₀	0.08 μM Compound: 311	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
NCI-H460	IC₅₀	0.21 μM Compound: 311	Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
NCI-H460	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
P388	IC₅₀	0.024 μM Compound: 6	Cytotoxicity against mouse P388 cells after 96 hrs by MTT assay Cytotoxicity against mouse P388 cells after 96 hrs by MTT assay	[PMID: 22148349]
P815	ED₅₀	2 μM Compound: Gliotoxin	Compound was evaluated for Thymidine incorporation in P815 cell lines Compound was evaluated for Thymidine incorporation in P815 cell lines	10.1016/S0960-894X(97)10052-X
PC-3	IC₅₀	0.39 μM Compound: 311	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability Cytotoxicity against human PC-3 cells assessed as reduction in cell viability	[PMID: 38181652]
PC-3	IC₅₀	15.87 μM Compound: 311	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay Cytotoxicity against human PC-3 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay	[PMID: 38181652]
RKO	IC₅₀	0.8 μM Compound: 311	Cytotoxicity against human RKO cells assessed as inhibition of cell growth measured after 48 hrs by MTT assay Cytotoxicity against human RKO cells assessed as inhibition of cell growth measured after 48 hrs by MTT assay	[PMID: 38181652]
SF-268	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
SF-268	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
U-937	IC₅₀	0.2 μM Compound: 311	Cytotoxicity against human U-937 cells assessed as reduction in cell viability Cytotoxicity against human U-937 cells assessed as reduction in cell viability	[PMID: 38181652]
U-937	IC₅₀	0.52 μM Compound: 311	Cytotoxicity against human U-937 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Cytotoxicity against human U-937 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 38181652]

体外実験

Gliotoxin (50 ng/ml, 48 hours) promotes the internalization of Aspergillus fumigatus by A549 type II human pneumocytes through inducing cofilin phosphorylation and actin cytoskeleton rearrangement^[3].
Gliotoxin (2.5%, 5%, 10%, 20% culture filtrates of Aspergillus fumigatus containing Gliotoxin, 16 hours) induces apoptosis in EL4 thymoma cells through Bak-dependent mechanisms and activation of caspase 3, leading to phosphatidylserine translocation and cell death^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[3]

Cell Line:	A549 type II human pneumocytes
Concentration:	50 ng/ml
Incubation Time:	48 hours
Result:	Induced cofilin phosphorylation, promoting actin cytoskeleton rearrangement and facilitating internalization of Aspergillus fumigatus.

体内実験

Gliotoxin (50 ng/ml, Intranasal administration, single dose) enhances the invasiveness of Aspergillus fumigatus in Hydrocortisone (HY-N0583)-induced immunosuppressed C57BL/6 mouse models by promoting lung tissue invasion and increasing fungal burden^[3].
Gliotoxin (Intranasal administration, single dose) significantly increases fungal burden in the lungs and mortality in Hydrocortisone (HY-N0583)-induced immunosuppressed BALB/c and 129/Sv mouse models, contributing to the virulence of Aspergillus fumigatus^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Hydrocortisone (HY-N0583)-induced immunosuppressed C57BL/6 mice^[3]
Dosage:	50 ng/ml
Administration:	Intranasal administration, single dose
Result:	Helped the gliP mutant strain (which cannot produce Gliotoxin) invade lung tissues, leading to increased fungal burden in the lungs of immunosuppressed mice.

Animal Model:	Hydrocortisone (HY-N0583)-induced immunosuppressed BALB/c and 129/Sv mouse models^[4]
Dosage:	Gliotoxin concentration not explicitly mentioned, present in Aspergillus fumigatus culture filtrates
Administration:	Intranasal administration of culture filtrates containing gliotoxin, single dose
Result:	Increased lung tissue fungal burden and mortality in immunosuppressed mice. The gliP deletion strain, which cannot produce gliotoxin, showed reduced virulence.

分子量

326.39

分子式

C₁₃H₁₄N₂O₄S₂

CAS 番号

67-99-2

Appearance

Solid

Color

White to off-white

SMILES

O=C1N([C@]2(C(N3[C@]1(CC4=CC=C[C@@H]([C@@]34[H])O)SS2)=O)CO)C

Structure Classification

Initial Source

Microorganisms

Aspergillus fumigatus

輸送条件

Room temperature in continental US; may vary elsewhere.

保管条件

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

溶剤 & 溶解度

体外:

DMSO : 5 mg/mL (15.32 mM; Need ultrasonic and warming; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

DMF : 5 mg/mL (15.32 mM; Need ultrasonic and warming)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	3.0638 mL	15.3191 mL	30.6382 mL
5 mM	0.6128 mL	3.0638 mL	6.1276 mL
10 mM	0.3064 mL	1.5319 mL	3.0638 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

一般には略語で表示されます：C₁V₁ = C₂V₂

濃度 _（開始）

体積 _（開始）

濃度 _（終了）

体積 _（終了）

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

純度とドキュメンテーション

純度: 99.51%

Select Batch:

データシート (285 KB) SDS (419 KB)

COA (258 KB) LCMS (96 KB)

取扱説明書 (2659 KB)

参考文献

[1]. Schlam D, et al. Gliotoxin Suppresses Macrophage Immune Function by Subverting Phosphatidylinositol 3,4,5-Trisphosphate Homeostasis. MBio. 2016 Apr 5;7(2):e02242. [Content Brief]

[2]. Coméra C, et al. Gliotoxin from Aspergillus fumigatus affects phagocytosis and the organization of the actin cytoskeleton by distinct signalling pathways in human neutrophils. Microbes Infect. 2007 Jan;9(1):47-54. Epub 2006 Dec 12. [Content Brief]

[3]. Zhang C, et al. Gliotoxin Induces Cofilin Phosphorylation to Promote Actin Cytoskeleton Dynamics and Internalization of Aspergillus fumigatus Into Type II Human Pneumocyte Cells. Front Microbiol. 2019 Jun 18;10:1345. [Content Brief]

[4]. Hubmann R, et al. Gliotoxin is a potent NOTCH2 transactivation inhibitor and efficiently induces apoptosis in chronic lymphocytic leukaemia (CLL) cells. Br J Haematol. 2013 Mar;160(5):618-29. [Content Brief]

[5]. Sugui JA, et al. Gliotoxin is a virulence factor of Aspergillus fumigatus: gliP deletion attenuates virulence in mice immunosuppressed with hydrocortisone. Eukaryot Cell. 2007 Sep;6(9):1562-9. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO / DMF	1 mM	3.0638 mL	15.3191 mL	30.6382 mL	76.5955 mL
	5 mM	0.6128 mL	3.0638 mL	6.1276 mL	15.3191 mL
	10 mM	0.3064 mL	1.5319 mL	3.0638 mL	7.6595 mL
	15 mM	0.2043 mL	1.0213 mL	2.0425 mL	5.1064 mL

Gliotoxin Related Classifications

Molarity Calculator
Dilution Calculator

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

質量		濃度		体積		分子量 *
	=		×		×

The dilution calculator equation

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

一般には略語で表示されます：C₁V₁ = C₂V₂

濃度 _（開始）	×	体積 _（開始）	=	濃度 _（終了）	×	体積 _（終了）
	×		=		×
C1		V1		C2		V2

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Gliotoxin67-99-2AspergillinApoptosisPKANF-κBBacterialFungalAntibioticProtein kinase ANuclear factor-κBNuclear factor-kappaBA549Immunosuppressed C57BL/6 miceInhibitorinhibitorinhibit

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Aspergillin (Synonyms: グリオトキシン; Gliotoxin)

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Complete Stock Solution Preparation Table

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