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3-bromo-5-phenyl Salicylic Acid Exclusive

Cayman Chemical Item Number 13574

NSC 109116 (CAS 4906-68-7)

3-bromo-5-phenyl Salicylic Acid (CAS 4906-68-7)

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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

1 Zhang, Y., Dufort, I., Rheault, P., et al. Characterization of a human 20α-hydroxysteroid dehydrogenase. J Mol Endocrinol 25 221-228 (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., Lin, C., Chiu, J., 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 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 138 821-829 (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 20a-hydroxysteroid dehydrogenase (AKR1C1). J Med Chem 52 3259-3264 (2009).

Synonyms
  • NSC 109116
Formal Name 5-​bromo-​4-​hydroxy-​[1,​1'-​biphenyl]-​3-​carboxylic acid
CAS Number 4906-68-7
Molecular Formula C13H9BrO3
Formula Weight 293.1
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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BrC1=CC(C2=CC=CC=C2)​=CC(C(O)​=O)​=C1O

Background Reading

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 20a-hydroxysteroid dehydrogenase (AKR1C1). J Med Chem 52 3259-3264 (2009).

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).

Wang, H., Lin, C., Chiu, J., 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 2019-2027 (2007).

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

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

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).

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Size Price Quantity Subtotal
1 mg $51.00 $0.00
5 mg $230.00 $0.00
10 mg $408.00 $0.00
25 mg $893.00 $0.00
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Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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