L-Chicoric Acid

• CAT Number: I004654
• CAS Number: 70831-56-0
• Molecular Formula: C22H18O12
• Molecular Weight: 474.374
• Purity: ≥95%
• Solubility: 10 mM in DMSO
• Storage: Desiccate at -20C
• IUPAC Name: (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
• InChI: InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
• InChIKey: YDDGKXBLOXEEMN-IABMMNSOSA-N
• SMILES: C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O

L-Chicoric acid is an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase in vitro and of HIV-1 replication in tissue culture.IC50 value:Target:In vitro: Using quantitative real-time polymerase chain reaction (PCR), l-CA inhibits integration at concentrations from 500 nM to 10 μM but also inhibits entry at concentrations above 1 μM [1]. l-Chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of Zidovudine plus a protease inhibitor (AG1350) [2]. L-chicoric acid inhibits integrase and that the drug is likely to interact at residues near the catalytic triad in the integrase active site [3].In vivo:

Reference

[1]. Ryan A Reinke, et al. l-Chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology
Volume 326, Issue 2, 1 September 2004, Pages 203–219

[2]. W Edward Robinson Jr., et al. l-Chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of Zidovudine plus a protease inhibitor (AG1350). Antiviral Research
Volume 39, Issue 2, August 1998, Pages 101–111

[3]. King PJ, et al. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. Journal of Virology, 1998, 72(10): 8420-8424