| Identification | Back Directory | [Name]
APICIDIN | [CAS]
183506-66-3 | [Synonyms]
OSI 2040
APICIDIN
Ccris 9163
Apicidin Ia
Apicidin
(OSI 2040)
APICIDIN, FUSARIUM SPECIES
CYCLO-[L-(2-AMINO-8-OXODECANOYL)-L-(N-METHOXYTRYPTOPHAN)-L-ISOLEUCYL-D-PIPECOLINYL
CYCLO-L-(2-AMINO-8-OXODEACANOYL)-L-(N-METHOXY-TRYPTOPHAN)-L-ISOLEUCYL-D-PIPECOLINYL
Cyclo(8-oxo-L-2-aMinodecanoyl-1-Methoxy-L-tryptophyl-L-isoleucyl-
D-2-piperidinecarbonyl)
Cyclo[(2S)-2-aMino-8-oxodecanoyl-1-Methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinecarbonyl]
CYCLO[(2S)-2-AMINO-8-OXODECANOYL-1-METHOXY-L-TRYPTOPHYL-L-ISOLEUCYL-(2R)-2-PIPERIDINEXCARBONYL]
Apicidin Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinecarbonyl] | [Molecular Formula]
C34H49N5O6 | [MDL Number]
MFCD03452661 | [MOL File]
183506-66-3.mol | [Molecular Weight]
623.78 |
| Chemical Properties | Back Directory | [Melting point ]
188-190oC | [density ]
1.27±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMSO: ~1mg/mL | [form ]
solid
| [pka]
13.09±0.70(Predicted) | [color ]
White | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. Compound is prone to oxidation. Protect from exposure to air. |
| Hazard Information | Back Directory | [Description]
Apicidin (183506-66-3) is a fungal toxin that is a potent, cell permeable inhibitor of histone deacetylases (HDAC’s).1?It also displays antitumor properties by inducing changes in p21WAF1/Cip1 and gelsolin gene expression causing cell cycle arrest in the G1?phase.2?Apicidin dramatically decreases HIF-1α protein levels and transcriptional activity in human and mouse tumor cell lines.3 | [Chemical Properties]
Solid | [Uses]
Apicidin is a cyclic peptide antibiotic with broad spectrum antiparasitic and antiprotozoan activity. Apicidin, a histone deacetylase inhibitor, is anti-angiogenic and induces apoptosis. | [Uses]
Apicidin is a potent (nM) cell permeable inhibitor of histone deacetylase. Also, Apicidin exhibits antiprotozoal and potential antimalarial properties. Apicidin has antiproliferative activity on HeLa
cells accompanied by cell arrest at the G1 phase. Apicidin induces selective changes in the expression of p21 and gelsolin. | [General Description]
Apicidin is a cyclic tetrapeptide fungal metabolite. | [Biochem/physiol Actions]
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. | [Enzyme inhibitor]
This fungal metabolite and potential oral chemotherapeutic agent (FW = 623.79 g/mol; CAS 183506-66-3), also known as [cyclo(N-O-methyl-L- tryptophanyl-L-isoleucinyl-D-pipecolinyl-L-2-amino-8-oxodecanoyl)], is an antiprotozoal agent. It is cell permeable and is a strong inhibitor of histone deacetylase (IC50 = 0.7 nM). Apicidin also inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. Apicidin’s low bioavailability of apicidin is mainly due to the P-gycoprotein-mediated efflux. | [storage]
-20°C | [References]
1) Darkin-Rattray,?et al. (1996)?Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase; Proc. Nat. Acad. Sci. USA,?93?13143
2) Han?et al. (2000)?Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin; Cancer Res.,?60?6068
3) Kim?et al. (2007)?Regulation of the HIF-1alpha stability by histone deacetylases; Oncol. Rep.?17?647 |
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