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Merck
모든 사진(3)

Key Documents

A6733

Sigma-Aldrich

Auranofin

≥98% (HPLC), powder, leukocyte activation pathway inhibitor

동의어(들):

1-Thio-β-D-glucopyranosatotriethylphosphine gold-2,3,4,6-tetraacetate, 3,4,5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium, SKF 39162

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About This Item

실험식(Hill 표기법):
C20H34AuO9PS
CAS Number:
Molecular Weight:
678.48
EC Number:
MDL number:
UNSPSC 코드:
51111800
PubChem Substance ID:
NACRES:
NA.77

product name

Auranofin, ≥98% (HPLC)

Quality Level

분석

≥98% (HPLC)

형태

powder

solubility

DMSO: ≥5 mg/mL

주관자

Prometheus

저장 온도

room temp

SMILES string

CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O

InChI

1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1

InChI key

AUJRCFUBUPVWSZ-XTZHGVARSA-M

애플리케이션

Auranofin inhibits both leukocyte activation pathways at multiple sites and the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. Auranofin also inhibits 5-lipoxygenase in human neutrophils, IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5 and selenoenzyme thioredoxin reductase (TrxR) which is involved in the defense against oxidative stress. Auranofin is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.

생화학적/생리학적 작용

Auranofin inhibits various leukocyte activation pathways at multiple sites. Auranofin inhibits the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. The compound also inhibits 5-lipoxygenase in human neutrophils. Auranofin is a disease-modifying antirheumatic drug (DMARD). The compound is a potent inhibitor of selenoenzyme thioredoxin reductase (TrxR), which is involved in defense against oxidative stress. Auranofin is an efficient inducer of mitochondrial membrane permeability transition pore in the presence of calcium ions related to its inhibition of mitochondrial thioredoxin reductase. Auranofin inhibits IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5.

특징 및 장점

This compound was developed by Prometheus. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

픽토그램

Skull and crossbonesHealth hazard

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


시험 성적서(COA)

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문서 라이브러리 방문

Jong-Lyel Roh et al.
Antioxidants & redox signaling, 27(2), 106-114 (2016-10-14)
The glutathione (GSH), thioredoxin (Trx), and Nrf2 systems represent a major defense against reactive oxygen species (ROS), the cellular imbalance of which in cancer promotes growth and therapeutic resistance. This study investigated whether targeting the GSH, Trx, and Nrf2 antioxidant
Samuel Pearson et al.
Chemical communications (Cambridge, England), 48(39), 4695-4697 (2012-04-05)
Polymeric versions of deacetylated auranofin, a gold complex with a sugar ligand, were prepared by post-modifying RAFT glycopolymers. Micellisation of a block copolymer containing pendant Au(I) units produced nanoparticles with an increased anti-proliferative effect against OVCAR-3 human ovarian carcinoma cells.
Lorenzo Turcano et al.
PLoS neglected tropical diseases, 12(11), e0006969-e0006969 (2018-11-27)
Trypanothione reductase (TR) is considered to be one of the best targets to find new drugs against Leishmaniasis. This enzyme is fundamental for parasite survival in the host since it reduces trypanothione, a molecule used by the tryparedoxin/tryparedoxin peroxidase system
David Leitsch
International journal for parasitology. Drugs and drug resistance, 7(3), 321-327 (2017-09-15)
The microaerophilic parasites Entamoeba histolytica, Trichomonas vaginalis, and Giardia lamblia annually cause hundreds of millions of human infections which are treated with antiparasitic drugs. Metronidazole is the most often prescribed drug but also other drugs are in use, and novel
Xiaodong Chen et al.
PloS one, 11(11), e0166386-e0166386 (2016-11-16)
Abnormal survival of retinal pigment epithelium (RPE) cells contributes to the pathogenesis of proliferative vitreoretinopathy (PVR), a sight-threatening disease. In this study, we explored the effect of the anti-rheumatic agent auranofin (AF) on RPE cell survival and studied the underlying

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