A polyketide and bacterial toxin
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Labeled Version(s)
3945413C28-Bongkrekic Acid
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Bongkrekic Acid

Item No. 38230

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
20-(carboxymethyl)-6R-methoxy-2,5,17S-trimethyl-2E,4Z,8Z,10E,14E,18E,20Z-docosaheptaenedioic acid
CAS Number
11076-19-0
Synonyms
  • Bongkrek Acid
Molecular Formula
C28H38O7
Formula Weight
486.6
Purity
≥98%
Formulation
A 100 µg/ml solution in 0.01M Tris buffer pH 7.5
Solubility(Learn about Variance in Solubility)
DMSO: Miscible
SMILES
OC(/C=C(CC(O)=O)\C=C\[C@@H](C)C/C=C/CC/C=C/C=C\C[C@@H](OC)/C(C)=C\C=C(C(O)=O)/C)=O
InChi Code
InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1
InChi Key
SHCXABJSXUACKU-WUTQZGRKSA-N
Origin
Bacterium/Pseudomonas gladioli
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $288

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    Product Description

    Bongkrekic acid is polyketide and bacterial toxin that has been found in B. gladioli.1,2 It is an inhibitor of ADP/ATP translocase (AAT), a carrier protein that imports ADP into the mitochondrial matrix and exports ATP into the intermembrane space.1,3 It prevents ADP import and inhibits mitochondrial respiration (Ki = 20 nM in isolated rat liver mitochondria).4,5 Bongkrekic acid induces cell death in MCF-7 human breast cancer cells deprived of estradiol for six months (EC50 = 2.58 µM).6 It is toxic to mice (LD50s = 0.68-6.84 mg/kg, p.o.).7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Henderson, P.J.F., and Lardy, H.A. Bongkrekic acid. An inhibitor of the adenine nucleotide translocase of mitochondria. The Journal of Biological Chemisty 245(6), 1319-1326 (1970).

    2. Xie, X., Khosla, C., and Cane, D.E. Elucidation of the stereospecificity of C-methyltransferases from trans-at polyketide synthases. J. Am. Chem. Soc. 139(17), 6102-6105 (2017).

    3. Lauqin, G.J., Dulpaa, A.M., Klein, G., et al. Isobongkrekic acid, a new inhibitor of mitochondrial ADP-ATP transport: Radioactive labeling and chemical and biological properties. Biochemistry 15(11), 2323-2327 (1976).

    4. Kligenberg, M., Grebe, K., and Heldt, H.W. On the inhibition of the adenine nucleotide translocation by bongkrekic acid. Biochem. Biophys. Res. Commun. 39(3), 344-351 (1970).

    5. Ruprecht, J.J., King, M.S., Zögg, T., et al. The molecular mechanism of transport by the mitochondrial ADP/ATP carrier. Cell 176(3), 435-447 (2019).

    6. Takeda, S., Okazaki, H., Kudo, T., et al. Bongkrekic acid as a warburg effect modulator in long-term estradiol-deprived MCF-7 breast cancer cells. Anticancer Res. 36(10), 5171-5182 (2016).

    7. Hu, W.J., Zhang, G.S., Chu, F.S., et al. Purification and partial characterization of flavotoxin A. Appl. Environ. Microbiol. 48(4), 690-693 (1984).