A cyclic tetrapeptide with diverse biological activities
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Apicidin

Item No. 10575

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
Acetonitrile: 1 mg/mlDMSO: 1 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.2 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $66

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    10 mg

    $473

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    Product Description

    Apicidin is a cyclic tetrapeptide that has been found in F. pallidoroseum and has diverse biological activities.1,2,3,4 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.1 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).1,2 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.3 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-β (1-40) (Αβ40) and Αβ42 in the hippocampus and cortex in an APPswe/PSEN1dE9 transgenic mouse model of Alzheimer's disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Darkin-Rattray, S.J., Gurnett, A.M., Myers, R.W., et al. Apicidin: A novel antiprotozoal agent that inhibits parasite histone deacetylase. Proc. Natl. Acad. Sci. USA 93(23), 13143-13147 (1996).

    2. Khan, N., Jeffers, M., Kumar, S., et al. Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. Biochem. J. 409(2), 581-589 (2008).

    3. Ueda, T., Takai, N., Nishida, M., et al. Apicidin, a novel histone deacetylase inhibitor, has profound anti-growth activity in human endometrial and ovarian cancer cells. Int. J. Mol. Med. 19, 301-308 (2007).

    4. Luo, B., Chen, J., Zhou, G.-F., et al. Apicidin attenuates memory deficits by reducing the Aβ load in APP/PS1 mice. CNS Neurosci. Ther. (0)0, 1-12 (2023).