Auranofin CAS: 34031-32-8
MF: C20H34AuO9PS
MW: 678.48

Auranofin (CAS 34031-32-8)

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Nomi alternativi: Auranofin also known an SKF 39162; 1-Thio-β-D-glucopyranosatotriethyl phosphine gold-2,3,4,6-tetraacetate; NSC 321521
Applicazione: Auranofin is a gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects and an inhibitor of 5-LO (5-lipoxygenase)/LTA synthase
Numero CAS: 34031-32-8
Purezza: ≥95%
Peso molecolare: 678.48
Formula molecolare: C20H34AuO9PS
Informazioni supplementari: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
Solo per uso in Ricerca. Non previsto per Uso Diagnostico o Terapeutico.
* Vedere Certificato di Analisi per informazioni sul lotto specifico (incluso il contenuto d'acqua).
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Auranofin is a gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects. Auranofin is described to block IgE (anti-IgE) and non-IgE histamine release from basophils and to inhibit the de novo synthesis of sulfidopeptide leukotriene C4 (LTC4) induced by anti-IgE from basophils and mast cells. At low concentrations, auranofin is described to stimulate leukotriene B4 (LTB4) synthesis through induction of LTA hydrolase activity, and at high concentrations is described to completely block all lipoxygenase products through inhibition of 5-LO (5-lipoxygenase)/LTA synthase. Auranofin also inhibits IκB kinase (IKK) by modifying Cys179 of the IKKβ subunit. Mitochondrial membrane permeability transition was induced by auranofin in the presence of Ca2+ ions, and demonstrated potent inhibition of mitochondrial thioredoxin reductase through interaction with the active site selenol group. Auranofin and other Au(I) compounds are described to quench reactive singlet oxygen species. Auranofin is an inhibitor of GSTP1, Stat3 and TrxR2.


Referenze

1. Corey, E.J., et al. 1987. Science. 236: 68-69. PMID: 3563489

2. Columbo, M., et al. 1990. Biochem. Pharmacol. 39: 285-291. PMID: 2105731

3. Betts, W.H., et al. 1990. Biochem. Pharmacol. 39: 1233-1237. PMID: 2157444

4. Rudkowski, R., et al. 1991. Biochem. Pharmacol. 41: 1921-1929. PMID: 1645553

5. Rigobello, M.P., et al. 2002. Br. J. Pharmacol. 136: 1162-1168. PMID: 12163349

Stato fisico :
Solid
Solubilità :
Soluble in DMSO (≥5 mg/ml), 100% ethanol (4 mg/ml), chloroform, and methanol.
CONSERVAZIONE :
Store at room temperature
Punto di scioglimento :
112-155° C
Attività ottica :
α20D -58.6, c = 1 in chloroform
IC50 :
TrxR: IC50 = 20 nM (human)
Ki Data :
The NADPH-reduced form of human cytosolic TrxR: Ki= 4 nM (human)
Solo per uso in Ricerca. Non previsto per Uso Diagnostico o Terapeutico.
WGK Germania :
3
RTECS :
MD6500000
PubChem CID :
Indice Merck :
14: 878
Numero MDL :
MFCD00080759
Numero EC :
251-801-9
Registro Beilstein :
8187029
SMILES :
CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]

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Auranofin (CAS 34031-32-8)  Citazioni prodotti

Vedi quanti altri hanno usato Auranofin (CAS 34031-32-8). Clicca sulla voce per laccesso a PubMed .

Ciatazioni 1 a10 di 33 totali

PMID: # 31639438  Dogar, I.|Dixon, S.|Gill, R.|Young, A.|Mallay, S.|Oldford, C.|Mailloux, RJ.| et al. 2020. Free Radic. Biol. Med. 146: 59-69.

PMID: # 31378680  Yin, N.|Liu, Y.|Khoor, A.|Wang, X.|Thompson, EA.|Leitges, M.|Justilien, V.|Weems, C.|Murray, NR.|Fields, AP.| et al. 2019. Cancer Cell. 36: 156-167.e7.

PMID: # 30861284  Fidyt, K.|Pastorczak, A.|Goral, A.|Szczygiel, K.|Fendler, W.|Muchowicz, A.|Bartlomiejczyk, MA.|Madzio, J.|Cyran, J.|Graczyk-Jarzynka, A.|Jansen, E.|Patkowska, E.|Lech-Maranda, E.|Pal, D.|Blair, H.|Burdzinska, A.|Pedzisz, P.|Glodkowska-Mrowka, E.|Demkow, U.|Gawle-Krawczyk, K.|Matysiak, M.|Winiarska, M.|Juszczynski, P.|Mlynarski, W.|Heidenreich, O.|Golab, J.|Firczuk, M.| et al. 2019. Mol Oncol. 13: 1180-1195.

PMID: # 31028540  Skaga, E.|Skaga, IØ.|Grieg, Z.|Sandberg, CJ.|Langmoen, IA.|Vik-Mo, EO.| et al. 2019. J. Cancer Res. Clin. Oncol. 145: 1495-1507.

PMID: # 31298580  Tharmalingam, N.|Ribeiro, NQ.|da Silva, DL.|Naik, MT.|Cruz, LI.|Kim, W.|Shen, S.|Dos Santos, JD.|Ezikovich, K.|D'Agata, EM.|Mylonakis, E.|Fuchs, BB.| et al. 2019. Future Med Chem. 11: 1417-1425.

PMID: # 31231607  Dabiri, Y.|Abu El Maaty, MA.|Chan, HY.|Wölker, J.|Ott, I.|Wölfl, S.|Cheng, X.| et al. 2019. Front Oncol. 9: 438.

PMID: # 30873389  Liu, H. et al. 2019. Front Cell Infect Microbiol. 9: 37.

PMID: # 27581528  Zhang, L. et al. 2016. Free Radic. Biol. Med. 99: 426-435.

PMID: # 26530353  You, BR. et al. 2016. Oncology reports. 35: 546-51.

PMID: # 26157704  Schott, C. et al. 2015. Front Oncol. 5: 131.

Ciatazioni 1 a10 di 33 totali
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