Apicidin

Apicidin is a cyclic tetrapeptide that has been found in F. pallidoroseum and has diverse biological activities. It is active against E. tenella, T. gondii, P. falciparum, C. parvum, N. caninum, B. jellisoni, and C. bigenetica (MICs = 62, 8, 125, 30, 15, 4, and 8 ng/ml, respectively) and decreases the percentage of P. berghei-infected erythrocytes in a mouse model of malaria when administered at a dose of 25 mg/kg. Apicidin inhibits histone deacetylase (HDAC) activity in E. tenella homogenates (IC50 = 0.7 nM) and recombinant human HDAC2 and HDAC3 (EC50s = 120 and 43 nM, respectively). It inhibits the proliferation of SKOV3 ovarian cancer cells (EC50 = 1-2.5 µM) and induces cell cycle arrest at the G0/G1 phase in SKOV3 cells when used at a concentration of 50 nM. Apicidin (3.5 mg/kg every two days, i.p.) prevents decreases in freezing time in contextual fear conditioning tests, indicating a reversal of memory deficits, and accumulation of amyloid-beta (1-40) (?beta40) and ?beta42 in the hippocampus and cortex in an APPswe/PSEN1dE9 transgenic mouse model of Alzheimer's disease.Formal Name: cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinecarbonyl]. CAS Number: 183506-66-3. Synonyms: OSI 2040. Molecular Formula: C34H49N5O6. Formula Weight: 623.8. Purity: >90%. Formulation: (Request formulation change), A crystalline solid. Solubility: Acetonitrile: 1 mg/ml, DMSO: 1 mg/ml, DMSO:PBS(pH 7.2) (1:4): 0.2 mg/ml. lambdamax: 221 nm. SMILES: O=C1C([C@@H](C)CC)NC([C@H](CC2=CN(OC)C3=C2C=CC=C3)NC([C@H](CCCCCC(CC)=O)NC([C@@]4([H])CCCCN41)=O)=O)=O. InChi Code: 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-. InChi Key: JWOGUUIOCYMBPV-GTMVXCKXSA-N.