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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)

See more	Inhibitors (493) Cancer (606) Endocrinology (335)

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 (K_i = 140 nM) over AKR1C2 (K₁ = 1.97 µM) and AKR1C3 (K_i = 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	Copy SMILES to clipboard 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).

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

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).

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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
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-11. Prices are subject to change without notice.

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