An OATP and MDR2 substrate and inhibitor
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Bromosulfalein

Item No. 21058

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,3'-(4,5,6,7-tetrabromo-3-oxo-1(3H)-isobenzofuranylidene)bis[6-hydroxy-benzenesulfonic acid, disodium salt
CAS Number
71-67-0
Synonyms
  • Bromosulfophthalein
  • Bromosulphalein
  • Sulfobromophthalein
  • Sulphobromophthalein
Molecular Formula
C20H8Br4O10S2 • 2Na
Formula Weight
838.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlEthanol: slightly solublePBS (pH 7.2): 1 mg/ml
λmax
230 nm
SMILES
O=C1OC(C2=CC(S([O-])(=O)=O)=C(O)C=C2)(C3=CC(S([O-])(=O)=O)=C(O)C=C3)C4=C(Br)C(Br)=C(Br)C(Br)=C41.[Na+].[Na+]
InChi Code
InChI=1S/C20H10Br4O10S2.2Na/c21-15-13-14(16(22)18(24)17(15)23)20(34-19(13)27,7-1-3-9(25)11(5-7)35(28,29)30)8-2-4-10(26)12(6-8)36(31,32)33;;/h1-6,25-26H,(H,28,29,30)(H,31,32,33);;/q;2*+1/p-2
InChi Key
GHAFORRTMVIXHS-UHFFFAOYSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $35

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    5 g

    $94

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    10 g

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    Product Description

    Bromosulfalein has been commonly used as both a substrate and inhibitor of organic anionic transporting polypeptide 1B1 (OATP1B1), OATP1B3, OATP1A2, and OATP2B1, as well as multidrug resistance protein 2 (MDR2).1,2,3,4,5,6 It has also been used for in vivo studies of liver and biliary system function and as an anionic dye for the quantitative estimation of protein levels in tissue homogenates or purified samples.7,8,9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Consortium, I.T., Giacomini, K.M., Huang, S.M., et al. Membrane transporters in drug development. Nat. Rev. Drug Dis. 9(3), 215-236 (2010).

    2. Izumi, S., Nozaki, Y., Komori, T., et al. Substrate-dependent inhibition of organic anion transporting polypeptide 1B1: Comparative analysis with prototypical probe substrates estradiol-17β-glucuronide, estrone-3-sulfate, and sulfobromophthalein. Drug Metab. Dispos. 41(10), 1859-1866 (2013).

    3. Karlgren, M., Vildhede, A., Norinder, U., et al. Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): Influence of protein expression on drug-drug interactions. J. Med. Chem. 55(10), 4740-4763 (2012).

    4. Patik, I., Székely, V., Német, O., et al. Identification of novel cell-impermeant fluorescent substrates for testing the function and drug interaction of organic anion-transporting polypeptides, OATP1B1/1B3 and 2B1. Sci. Rep. 8(1), 2630 (2018).

    5. Zhang, J., Zhang, M., Sun, B., et al. Hyperammonemia enhances the function and expression of P-glycoprotein and Mrp2 at the blood-brain barrier through NF-κB. J. Neurochem. 131(6), 791-802 (2014).

    6. Matsson, P., Pedersen, J.M., Norinder, U., et al. Identification of novel specific and general inhibitors of the three major human ATP-binding cassette transporters P-gp, BCRP and MRP2 among registered drugs. Pharm Res. 26(8), 1816-1831 (2009).

    7. Itoh, T., Itagaki, S., Sasaki, K., et al. Pharmacokinetic modulation of irinotecan metabolites by sulphobromophthalein in rats. J. Pharm. Pharmacol. 56(6), 809-812 (2004).

    8. Oh, J.H., Park, S.E., Shim, C.K., et al. Biliary clearance of bromosulfophthalein in anesthetized and freely moving conscious rat. Biopharm. Drug. Dispos. 30(2), 94-98 (2009).

    9. McGuire, J.C., Taylor, P., and Greene, L.A. A modified bromosulfalein assay for the quantitative estimation of protein. Anal. Biochem. 83(1), 75-81 (1977).