A component of the antimycin A complex
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Antimycin A3

Item No. 21998

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2(or 3)-methyl-butanoic acid, (2R,3S,6S,7R,8R)-3-[[3-(formylamino)-2-hydroxybenzoyl]amino]-8-butyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester
CAS Number
522-70-3
Synonyms
  • Blastomycin
  • NSC 58239
Molecular Formula
C26H36N2O9
Formula Weight
520.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC(C)CC(O[C@@H]([C@@H]1C)[C@H](C(O[C@@H]([C@@H](C(O1)=O)NC(C(C=CC=C2NC([H])=O)=C2O)=O)C)=O)CCCC)=O
InChi Code
InChI=1S/C26H36N2O9/c1-6-7-9-18-23(37-20(30)12-14(2)3)16(5)36-26(34)21(15(4)35-25(18)33)28-24(32)17-10-8-11-19(22(17)31)27-13-29/h8,10-11,13-16,18,21,23,31H,6-7,9,12H2,1-5H3,(H,27,29)(H,28,32)/t15-,16+,18-,21+,23+/m1/s1
InChi Key
PVEVXUMVNWSNIG-PDPGNHKXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $219

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    5 mg

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    Product Description

    Antimycin A3 is a component of the antimycin A complex that is more polar than antimycin A1 (Item No. 19433) and antimycin A2 (Item No. 21997) but not antimycin A4 (Item No. 21999).1,2,3,4 Antimycin A3 binds to the Q(inner) site of mitochondrial complex III (cytochrome bc1) and inhibits mitochondrial respiration (IC50 = 38 nM in isolated rat liver mitochondria).5 It also inhibits ATP-citrate lyase with a Ki value of 60.1 µM, and it stimulates the production of reactive oxygen species.6,7 In molecular modeling studies, antimycin binds to a mutant form of Bcl-2 (hBcl-2Δ22) and has a Kd value of 0.82 µM for binding to a recombinant mutant form of Bcl-2 (rhBcl-2Δ22) in an isothermal calorimetry assay.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liu, W.-C., and Strong, F.M. The chemistry of antimycin A. VI. Separation and properties of antimycin A subcomponents. J. Am. Chem. Soc. 81(16), 4387-4390 (1959).

    2. Wang, J., Wen, Y., Chen, X., et al. Preparative separation of six antimycin A components from antimycin fermentation broth by high-speed counter-current chromatography. J. Chromatogr. A. 1217(36), 5687-5692 (2010).

    3. Dunshee, B.R., Leben, C., Keitt, G.W., et al. The isolation and properties of antimycin A. J. Am Chem. Soc. 71(7), 2436-2437 (1949).

    4. Kluepfel, D., Sehgal, S.N., and Vezina, C. Antimycin A components. I. Isolation and biological activity. J. Antibiot. (Tokyo) 23(2), 75-80 (1970).

    5. Miyoshi, H., Kondo, H., Oritani, T., et al. Inhibition of electron transport of rat liver mitochondria by unnatural (−)-antimycin A3. FEBES Lett. 292(1-2), 61-63 (1991).

    6. Barrow, C.J., Oleynek, J.J., Marinelli, V., et al. Antimycins, inhibitors of ATP-citrate lyase, from a Streptomyces sp. J. Antibiot. (Tokyo) 50(9), 729-733 (1997).

    7. Takimoto, H., Machida, K., Ueki, M., et al. UK-2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-02 IV. Comparative studies of UK-2A with antimycin A3 on cytotoxic activity and reactive oxygen species generation in LLC-PK1 cells. J. Antibiot. (Tokyo) 52(5), 480-484 (1999).

    8. Kim, K.M., Giedt, C.D., Basanez, G., et al. Biophysical characterization of recombinant human Bcl-2 and its interactions with an inhibitory ligand, antimycin A. Biochemistry 40(16), 4911-4922 (2001).