AT-130 is a phenylacrylamide analogue and a potent non-nucleoside inhibitor of HBV (hepatitis B virus) replication. AT-130 inhibits viral DNA synthesis with EC50 of 0.13 μM. AT-130 can inhibit wild-type and mutant HBV (hepatitis B virus). AT-130 has anti-HBV (hepatitis B virus) activity in liver cancer/tumor cells.

Physicochemical Properties

Molecular Formula	C22H22BRN3O5
Molecular Weight	488.3312
Exact Mass	487.074
CAS #	211364-06-6
PubChem CID	3002812
Appearance	White to off-white solid powder
LogP	4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Heavy Atom Count	31
Complexity	694
Defined Atom Stereocenter Count	0
SMILES	COC1=CC=CC=C1/C(=C(/C(=O)N2CCCCC2)\NC(=O)C3=CC=C(C=C3)[N+](=O)[O-])/Br
InChi Key	OQIUTYABZMBBME-FMQUCBEESA-N
InChi Code	InChI=1S/C22H22BrN3O5/c1-31-18-8-4-3-7-17(18)19(23)20(22(28)25-13-5-2-6-14-25)24-21(27)15-9-11-16(12-10-15)26(29)30/h3-4,7-12H,2,5-6,13-14H2,1H3,(H,24,27)/b20-19+
Chemical Name	N-[(E)-1-bromo-1-(2-methoxyphenyl)-3-oxo-3-piperidin-1-ylprop-1-en-2-yl]-4-nitrobenzamide
Synonyms	AT-130 AT130 AT 130
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

AT-130 suppresses rtL180M (IC50=9.8 μM), rtM204I (IC50=35.6 μM), and Wt (IC50=2.4 μM) HBV [1]. HepG2 cells transduced with HBV baculovirus showed dose-dependent suppression of wt HBV replication when treated with AT-130 (0.1, 1, 5, 10, 100 μM) for 7 days. When AT-130 is present, encapsidated HBV DNA is reduced by 50% (IC50) at 2.5 μM and by 90% (IC90) at 18.5 μM [1]. At concentrations as high as 250 μM, AT-130 does not cause harm to HepG2 or Huh-7 cells [1]. By directly inhibiting the HBV endogenous DNA polymerase reaction in Huh 7 or HepG2 cells, AT-130 (0.005, 0.05, 0.5, 5, 50 μM) does not inhibit HBV DNA synthesis. While AT-130 has no effect on viral DNA polymerase activity or core protein translation, it suppresses the replication of HBV DNA in liver cancer cells [3]. While it decreases encapsidated RNA, AT-130 (2.5, 18.5 μM) had little effect on total HBV RNA. The activity of protein expression vectors and the synthesis of nucleocapsids or core proteins are unaffected by AT-130 [3].

References

[1]. Phenylpropenamide derivatives AT-61 and AT-130 inhibit replication of wild-type and lamivudine-resistant strains of hepatitis B virus in vitro. Antimicrob Agents Chemother. 2002 Sep;46(9):3057-60. [2]. Phenylpropenamide derivatives as inhibitors of hepatitis B virus replication. Bioorg Med Chem Lett. 2000 Dec 4;10(23):2687-90. [3]. The phenylpropenamide derivative AT-130 blocks HBV replication at the level of viral RNA packaging. Antiviral Res. 2007 Nov;76(2):168-77.

Solubility Data

Solubility (In Vitro)

DMSO : ~25 mg/mL (~51.19 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.0478 mL	10.2390 mL	20.4780 mL
	5 mM	0.4096 mL	2.0478 mL	4.0956 mL
	10 mM	0.2048 mL	1.0239 mL	2.0478 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.