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5-bromo-3-phenyl Salicylic Acid

Cayman Chemical Item Number 13379

(CAS 99514-99-5)

5-bromo-3-phenyl Salicylic Acid (CAS 99514-99-5)

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Description

The aldo-keto reductase (AKR) enzymes constitute a family of related NADP-dependent oxidoreductases.The 1C subfamily (AKR1C) includes four human hydroxysteroid dehydrogenases (HSD), 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 5-bromo-3-phenyl Salicyclic acid selectively inhibits AKR1C1 (Ki = 140 nM) over AKR1C2 (K1 = 1.97 µM) and AKR1C3 (Ki = 21 µM).6 It does not inhibit AKR1C4 at 100 µM.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).

Formal Name 5-​bromo-​2-​hydroxy-​[1,​1'-​biphenyl]-​3-​carboxylic acid
CAS Number 99514-99-5
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)​=C(O)​C(C(O)​=O)​=C1

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).

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).

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).

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).

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).

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

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Size Price Quantity Subtotal
1 mg $43.00 $0.00
5 mg $194.00 $0.00
10 mg $344.00 $0.00
25 mg $753.00 $0.00
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Pricing updated 2012-05-26. Prices are subject to change without notice.

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