AM580

• CAT Number: I000150
• CAS Number: 102121-60-8
• Molecular Formula: C22H25NO3
• Molecular Weight: 351.44
• Purity: ≥95%
• Target: RAR/RXR
• Solubility: DMSO: ≥ 45 mg/mL
• Storage: -20°C
• IUPAC Name: 4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid
• InChI: InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
• InChIKey: SZWKGOZKRMMLAJ-UHFFFAOYSA-N
• SMILES: CC1(CCC(C2=C1C=CC(=C2)C(=O)NC3=CC=C(C=C3)C(=O)O)(C)C)C

AM580(Cat No.:I000150), also known as Ro 40-6055; NSC608001; CD336, is a stable retinoic acid derivative originally synthesized as a RARα agonist. AM580 is also a potent inducer of granulocyte maturation in NB4 (an APL-derived cell line) and freshly isolated APL blasts.

Reference

1:Reversal by RARα agonist Am580 of c-Myc-induced imbalance in RARα/RARγ expression during MMTV-Myc tumorigenesis. Bosch A, Bertran SP, Lu Y, Garcia A, Jones AM, Dawson MI, Farias EF.Breast Cancer Res. 2012 Aug 24;14(4):R121. doi: 10.1186/bcr3247. PMID: 22920668 Free PMC Article2:Mechanism of inhibition of MMTV-neu and MMTV-wnt1 induced mammary oncogenesis by RARalpha agonist AM580. Lu Y, Bertran S, Samuels TA, Mira-y-Lopez R, Farias EF.Oncogene. 2010 Jun 24;29(25):3665-76. doi: 10.1038/onc.2010.119. Epub 2010 May 10. PMID: 20453882 Free PMC Article3:Synthesis and pharmacological characterization of Disila-AM80 (Disila-tamibarotene) and Disila-AM580, silicon analogues of the RARalpha-selective retinoid agonists AM80 (Tamibarotene) and AM580. Tacke R, Müller V, Büttner MW, Lippert WP, Bertermann R, Daiss JO, Khanwalkar H, Furst A, Gaudon C, Gronemeyer H.ChemMedChem. 2009 Nov;4(11):1797-802. doi: 10.1002/cmdc.200900257. No abstract available. PMID: 19790202 4:AM580, a stable benzoic derivative of retinoic acid, has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells. Gianní M, Li Calzi M, Terao M, Guiso G, Caccia S, Barbui T, Rambaldi A, Garattini E.Blood. 1996 Feb 15;87(4):1520-31. PMID: 8608243 Free Article5:Determination of the retinobenzoic acid derivative Am580 in rat plasma by high-performance liquid chromatography. Dimitrova B, Caccia S, Garattini E, Guiso G.J Chromatogr B Biomed Appl. 1995 May 19;667(2):301-6. PMID: 7663703 6:Synthetic retinoids, retinobenzoic acids, Am80, Am580 and Ch55 regulate morphogenesis in chick limb bud. Tamura K, Kagechika H, Hashimoto Y, Shudo K, Ohsugi K, Ide H.Cell Differ Dev. 1990 Oct;32(1):17-26. PMID: 2090329