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Acetyl Podocarpic Acid Anhydride Exclusive

Cayman Chemical Item Number 10007686

APD (CAS 344327-48-6)

Acetyl Podocarpic Acid Anhydride (CAS 344327-48-6)

See more	Nuclear Receptors (86) Steroids (37) Atherosclerosis (323) Oxidative Injury (258)

Description

The liver X receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands are oxysterols.¹ Acetyl podocarpic acid anhydride (APD) is potent, semi-synthetic LXR agonist derived from extracts of the mayapple. APD acting through LXR in concert with the retinoid X receptor (RXR), its heterodimerization partner, induces the expression of the ABCA1 reverse cholesterol transporter.² This acts to increase the efflux of cholesterol from enterocytes and thus inhibits the overall absorption of cholesterol (ED₅₀ value of 1 nM).³ In transient transactivation assays, APD was found to be approximately 1,000 times more potent and have 8-10-fold greater maximal stimulation of LXR than 22(R)-hydroxy cholesterol.^3,4 APD can be used as a positive control for the testing of LXR agonists, which have potential as therapeutic agents for the treatment of atherosclerosis.

1 Repa, J.J., Turley, S.D., Lobaccaro, J.A., et al. Regulation of absorption and ABC1-mediated efflux of cholesterol by RXR heterodimers. Science 289 1524-1529 (2000).

2 Costet, P., Luo, Y., Wang, N., et al. Sterol-dependent transactivation of the ABC1 promoter by the liver X receptor/retinoid X receptor. J Biol Chem 275 28240-28245 (2000).

3 Sparrow, C.P., Baffic, J., Lam, M., et al. A potent synthetic LXR agonist is more effective than cholesterol loading at inducing ABCA1 mRNA and stimulating cholesterol efflux. J Biol Chem 277(12) 10021-10027 (2002).

4 Singh, S.B., Ondeyka, J.G., Liu, W., et al. Discovery and development of dimeric podocarpic acid leads as potent agonists of liver X receptor with HDL cholesterol raising activity in mice and hamsters. Bioorg Med Chem Lett 15 2824-2828 (2005).

Synonyms	APD
Formal Name	6-(acetyloxy)-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-1-phenanthrenecarboxylic acid, anhydride
CAS Number	344327-48-6
Molecular Formula	C₃₈H₄₆O₇
Formula Weight	614.8
Formulation	A crystalline solid
Purity	>98%
λ_max	208, 268 nm
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CC(=O)Oc1ccc2CC[C@H]3[C@](C)(CCC[C@]3(C)c2c1)[C@@H](=O)O[C@H](=O)[C@@]1(C)CCC[C@]2(C)c3cc(ccc3CC[C@@H]12)OC(=O)C

Background Reading

Repa, J.J., Turley, S.D., Lobaccaro, J.A., et al. Regulation of absorption and ABC1-mediated efflux of cholesterol by RXR heterodimers. Science 289 1524-1529 (2000).

Cole, A.R., Hall, N.E., Treutlein, H.R., et al. Disulfide bond structure and N-glycosylation sites of the extracellular domain of the human interleukin-6 receptor. J Biol Chem 274 7207-7215 (1999).

Sparrow, C.P., Baffic, J., Lam, M., et al. A potent synthetic LXR agonist is more effective than cholesterol loading at inducing ABCA1 mRNA and stimulating cholesterol efflux. J Biol Chem 277(12) 10021-10027 (2002).

Singh, S.B., Ondeyka, J.G., Liu, W., et al. Discovery and development of dimeric podocarpic acid leads as potent agonists of liver X receptor with HDL cholesterol raising activity in mice and hamsters. Bioorg Med Chem Lett 15 2824-2828 (2005).

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Size	Price	Quantity	Subtotal
1 mg	$18.00		$0.00
5 mg	$81.00		$0.00
10 mg	$144.00		$0.00
50 mg	$630.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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