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AM580 CAS: 102121-60-8

Category: Inhibitors
Product Name: AM580
Cat No: I000150
CAS No: 102121-60-8
Synonyms: None
Molecular Formula: C22H25NO3
Molecular Weight: 351.4
SMILES: OC(C1=CC=C(NC(C2=CC(C(C)(C)CCC3(C)C)=C3C=C2)=O)C=C1)=O
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
Solubility: DMSO: ≥ 45 mg/mL
Target: RAR/RXR
Storage: Store at -20°C
CAS 102121-60-8,AM580
  • Description

AM580(Am-580; Ro 40-6055; NSC608001; CD336) is a stable retinobenzoic derivative originally synthesized as a RARα agonist.
IC50 value:
Target: RARα agonist
in vitro: AM580 is a powerful inducer of granulocytic maturation in NB4, an APL-derived cell line, and in freshly isolated APL blasts. After treatment of APL cells with AM580 either alone or in combination with granulocyte colony-stimulating factor (G-CSF), the compound induces granulocytic maturation, as assessed by determination of the levels of leukocyte alkaline phosphatase, CD11b, CD33, and G-CSF receptor mRNA, at concentrations that are 10- to 100-fold lower than those of ATRA necessary to produce similar effects [1].
in vivo: A dose of 0.3mg/kg/day of Am580, was tested by treating 10 FVB mice for 4 months; no overt toxicity was found in liver, lungs, kidney, and spleen [2]. Treatment of MMTV-Myc mice with the RARα-selective agonist Am580 led to significant inhibition of mammary tumor growth (~90%, P<0.001), lung metastasis (P<0.01) and extended tumor latency in 63% of mice. Immunocytochemical analysis showed that in these mice, RARα responsive genes such as Cyp26A1, E-cadherin, cellular retinol-binding protein 1 (CRBP1) and p27, were up-regulated [3].

  • Spec

Appearance:Solid powder
Purity: > 98%

  • References


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 Article
2: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 Article
3: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 Article
5: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


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