An internal standard for the quantification of bongkrekic acid
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Unlabeled Version(s)
38230Bongkrekic Acid
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13C28-Bongkrekic Acid

Item No. 39454

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-((carboxy-13C)methyl-13C)-6-(methoxy-13C)-2,5,17-tri(methyl-13C)docosa-2,4,8,10,14,18,20-heptaenedioic-1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22-13C22 acid
Synonyms
  • 13C28-Bongkrek Acid
Molecular Formula
[13C]28H38O7
Formula Weight
514.4
Purity
≥98%
Formulation
A 5 µg/ml solution in methanol
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O[13C](/[13CH]=[13C]([13CH2][13C](O)=O)\[13CH]=[13CH]\[13C@@H]([13CH3])[13CH2]/[13CH]=[13CH]/[13CH2][13CH2]/[13CH]=[13CH]/[13CH]=[13CH]\[13CH2][13C@@H](O[13CH3])/[13C]([13CH3])=[13CH]\[13CH]=[13C]([13C](O)=O)/[13CH3])=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/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1,11+1,12+1,13+1,14+1,15+1,16+1,17+1,18+1,19+1,20+1,21+1,22+1,23+1,24+1,25+1,26+1,27+1,28+1
InChi Key
SHCXABJSXUACKU-LGIAGIHQSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1.2 ml

    $1,095

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    Product Description

    13C28-Bongkrekic Acid is intended for use as an internal standard for the quantification of bongkrekic acid (Item No. 38230) by GC- or LC-MS. 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).