A8851

Apicidin

≥98% (HPLC), from microbial

• Synonyme(s) : Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]
• Formule empirique (notation de Hill) : C₃₄H₄₉N₅O₆
• CAS Number: 183506-66-3
• Poids moléculaire : 623.78
• Numéro MDL: MFCD03452661
• Code UNSPSC : 12352200
• ID de substance PubChem : 329771019
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: microbial
• Niveau de qualité: 200
• Stérilité: non-sterile
• Essai: ≥98% (HPLC)
• Forme: solid
• Solubilité: DMSO: ~1 mg/mL
• Spectre d'activité de l'antibiotique: parasites
• Mode d’action: enzyme | inhibits
• Conditions d'expédition: wet ice
• Température de stockage: −20°C
• Chaîne SMILES: [H][C@]12CCCCN1C(=O)[C@@H](NC(=O)[C@H](Cc3cn(OC)c4ccccc34)NC(=O)[C@H](CCCCCC(=O)CC)NC2=O)C(C)CC
• InChI: 1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22?,26-,27-,29+,30?/m0/s1
• Clé InChI: JWOGUUIOCYMBPV-PYAAAQPJSA-N

Description

Description générale

Apicidin is a cyclic tetrapeptide fungal metabolite.

Application

Apicidin has been used as a histone deacetylase 2 (HDAC2) inhibitor to study its effects on 5-lipoxygenase (5-LO) mRNA expression in cell lines of Mono Mac6. It has also been used to study the effects of toll-like receptor 8 (TLR-8) stimulation and histone modification on the expression of an activator protein 1 [AP-1] family member(Fra-2) and tissue inhibitor of metalloproteinases 1 (TIMP-1) in monocytes.

Actions biochimiques/physiologiques

Apicidin is a potent inhibitor of histone deacetylase (HDAC). It particularlyinhibits histone deacetylase 1 and 3 (HDAC1 and HDAC3). Apicidin exhibits anti-protozoal activity against apicomplexan metabolite produced by parasites. It also possesses anti-proliferative activity against several cancer cell lines. Apicidin shows anti-cancer activity against human acute promyelocytic leukemia cell.

Potent (nM) cell permeable inhibitor of histone deacetylase.

Caractéristiques et avantages

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Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges