A mixture of macrotetralide antibiotics that act as ionophores
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Nonactin, Monactin, and Dinactin Mixture

Item No. 19468

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2R,5R,7R,10S,11S,14S,16S,19R,20R,23R,25R,28S,29S,32S,34S)-2,5,11,14,20,23,29,32-octamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
Molecular Formula
C40H64O12 (for Nonactin)
Formula Weight
736.9
Purity
≥95% (mixture of homologues)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 0.25 mg/mlEthanol: 1 mg/ml
SMILES
O=C(O[C@@H](C)C[C@@]1([H])O[C@]([C@@H](C)C(O[C@H](C)C[C@]2([H])O[C@@]3([H])CC2)=O)([H])CC1)[C@@H](C)[C@]4([H])CC[C@@](C[C@@H](C)OC([C@H](C)[C@@]5([H])CC[C@](C[C@H](C)OC([C@H]3C)=O)([H])O5)=O)([H])O4
InChi Code
InChI=1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32
InChi Key
RMIXHJPMNBXMBU-QIIXEHPYSA-N
Origin
Bacterium/Streptomyces griseus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Nonactin, monactin, and dinactin mixture is a macrotetralide antibiotic.1 This product is a mixture of the macrotetralide antibiotic homologs nonactin, monactin (Item No. 25742), and dinactin (Item No. 20752) that all act as ionophores for monovalent cations.2,3,4,5,6,7 Nonactin is a mitochondrial membrane uncoupler and an inhibitor of adenine nucleotide translocase (ANT; IC50s = 4.4, 3.3, 4.7, and 3.3 µM for recombinant human ANT1-4, respectively).8,9 It selectively induces apoptosis in cancer cells and induces tumor regression in mouse xenograft models expressing mutant β-catenin over cancer cells and xenografts expressing wild-type β-catenin.8 Monactin induces swelling of rat liver mitochondria in medium containing either potassium or sodium, stimulates respiration, and uncouples oxidative phosphorylation.10 It also inhibits Wnt signaling via inhibition of TCF-β-catenin transcriptional activity.11 Dinactin inhibits T cell proliferation and cytokine production in vitro and reduces pulmonary eosinophilia in antigen-challenged mice.12

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pampaloni, F., Mayer, B., Kabat Vel-Job, K., et al. A novel cellular spheroid-based autophagy screen applying live fluorescence microscopy identifies nonactin as a strong inducer of autophagosomal turnover. SLAS Discov. 22(5), 558-570 (2017).

    2. Hall, J.E., and Latorre, R. Nonactin-K+ complex as a probe for membrane asymmetry. Biophys.J. 16(1), 99-103 (1976).

    3. Browne, A., and O'Donnell, M.J. Ammonium secretion by Malpighian tubules of Drosophila melanogaster: Application of a novel ammonium-selective microelectrode. J. Exp. Biol. 216(Pt 20), 3818-3827 (2013).

    4. Skulskii, I.A., Saris, N.-E.L., Savina, M.V., et al. Uptake of thallous ions by mitochondria is stimulated by nonactin but not by respiration alone. Eur. J. Biochem. 120(2), 263-266 (1981).

    5. Beck, J., Gerlach, H., Prelog, V., et al. Metabolic products of actinomycetes. XXXV. Constitution of the macrotetrolides, monactin, dinactin, and trinactin. Helv. Chim. Acta 45, 620-630 (1962).

    6. Harold, F.M., and Baarda, J.R. Effects of nigericin and monactin on cation permeability of Streptococcus faecalis and metabolic capacities of potassium-depleted cells. J. Bacteriol. 95(3), 816-823 (1968).

    7. Laprade, R., Grenier, F., Pagé-Dansereau, M., et al. Carrier-mediated ion transport in lipid bilayer membranes. Can. J. Biochem. Cell Biol. 62(8), 738-751 (1984).

    8. Shikata, Y., Kiga, M., Futamura, Y., et al. Mitochondrial uncoupler exerts a synthetic lethal effect against β-catenin mutant tumor cells. Cancer Sci. 108(4), 772-784 (2017).

    9. Zhang, Y., Tian, D., Matsuyama, H., et al. Human adenine nucleotide translocase (ANT) modulators identified by high-throughput screening of transgenic yeast. J. Biomol. Screen. 21(4), 381-390 (2016).

    10. Graven, S.N., Lardy, H.A., and Estrada-O, S. Antibiotics as tools for metabolic studies. 8. Effect of nonactin homologs on alkali metal cation transport and rate of respiration in mitochondria. Biochem. 6(2), 365-371 (1967).

    11. Tamai, Y., Toume, K., Arai, M.A., et al. Nonactin and related compounds found in a screening program for Wnt signal inhibitory activity. Heterocycles 84(2), 1245-1250 (2012).

    12. Umland, S.P., Shah, H., Jakway, J.P., et al. Effects of cyclosporin A and dinactin on T-cell proliferation, interleukin-5 production, and murine pulmonary inflammation. Am. J. Respir. Cell Mol. Biol. 20(3), 481-492 (1999).