Inhibitor of aldo-keto reductase 1C1 (AKR1C1)
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3-bromo-5-phenyl Salicylic Acid

Item No. 13574

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-bromo-4-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
CAS Number
4906-68-7
Synonyms
  • NSC 109116
Molecular Formula
C13H9BrO3
Formula Weight
293.1
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMF:PBS (pH 7.2) (1:9): 0.1 mg/mlDMSO: 12.5 mg/mlEthanol: 0.1 mg/ml
λmax
233, 326 nm
SMILES
BrC1=CC(C2=CC=CC=C2)=CC(C(O)=O)=C1O
InChi Code
InChI=1S/C13H9BrO3/c14-11-7-9(8-4-2-1-3-5-8)6-10(12(11)15)13(16)17/h1-7,15H,(H,16,17)
InChi Key
XVZSXNULHSIRCQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $72

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    5 mg

    $304

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    10 mg

    $537

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    25 mg

    $1,073

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    Product Description

    The aldo-keto reductase (AKR) enzymes constitute a family of related NADPH-dependent oxidoreductases. The 1C subfamily (AKR1C) includes four human hydroxysteroid dehydrogenases, with AKR1C1 being a 20α-HSD and the other three being 3α-HSDs. AKR1C1 metabolizes progesterone to an inactive progestin, 20α-hydroxy progesterone.1 In addition, AKR1C1 actions have been implicated in cancer and in the processing of neuroactive steroids involved in brain function.2,3,4,5 3-bromo-5-phenyl Salicylic acid selectively inhibits AKR1C1 (Ki = 4 nM) over AKR1C2 (Ki = 87 nM), AKR1C3 (Ki = 4.2 μM), and AKR1C4 (Ki = 18.2 μM).6 Moreover, it potently inhibits the metabolism of progesterone by bovine aortic endothelial cells overexpressing AKR1C1 (IC50 = 460 nM).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, Y., Dufort, I., Rheault, P., et al. Characterization of a human 20α-hydroxysteroid dehydrogenase. J. Mol. Endocrinol. 25(2), 221-228 (2000).

    2. Lewis, M.J., Wiebe, J.P., and Heathcote, J.G. Expression of progesterone metabolizing enzyme genes (AKR1C1, AKR1C2, AKR1C3, SRD5A1, SRD5A2) is altered in human breast carcinoma. BMC Cancer 4, 27 (2004).

    3. Wang, H.W., Lin, C.P., Chiu, J.H., et al. Reversal of inflammation-associated dihydrodiol dehydrogenases (AKR1C1 and AKR1C2) overexpression and drug resistance in nonsmall cell lung cancer cells by wogonin and chrysin. Int. J. Cancer 120(9), 2019-2027 (2007).

    4. Belelli, D., Herd, M.B., Mitchell, E.A., et al. Neuroactive steroids and inhibitory neurotransmission: Mechanisms of action and physiological relevance. Neuroscience 138(3), 821-829 (2006).

    5. Usami, N., Yamamoto, T., Shintani, S., et al. Substrate specificity of human 3(20)α-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol. Pharm. Bull. 25(4), 441-445 (2002).

    6. El-Kabbani, O., Scammells, P.J., Gosling, J., et al. Structure-guided design, synthesis, and evaluation of salicylic acid-based inhibitors targeting a selectivity pocket in the active site of human 20α-hydroxysteroid dehydrogenase (AKR1C1). J. Med. Chem. 52(10), 3259-3264 (2009).