Description
AM-580 (102121-60-8) is a retinoic acid analog acting as a RARα agonist (Kd = 8 nM).1 Induces or blocks differentiation depending on cell type and environment.2,3 In combination with CHIR-99021 it induces differentiation of human induced pluripotent stem cells (iPSCs) into intermediate mesoderm (80% induction rate in 5 days) capable of forming kidney structures.4 AM-580 exhibits anti-angiogenic activity in vivo, and induces differentiation of acute promyelocytic leukemia cells.5,6
Uses
Retinoic acid analog which acts as a selective RARα agonist with no affinity for RXRs. Induces differentiation in leukemia cell lines and inhibits angiogenesis in chick embryos.
Definition
ChEBI: An amidobenzoic acid obtained by formal condensation of the carboxy group of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzoic acid with the anilino group of 4-aminobenzoic acid. A selective RARalpha agonist.
General Description
AM580 is a retinobenzoic derivative and a RAR-α (retinoic acid receptor-α) agonist. It stimulates the maturation of granulocytes in NB4 promyelocytic leukemia cell line and APL (acute promyelocytic leukemia) blasts. AM580 suppresses endometrial cancer cell proliferation.
Biological Activity
An analog of retinoic acid that acts as a selective RAR α agonist (EC 50 values are 0.3, 8.6 and 13 nM for RAR α , RAR β and RAR γ respectively). Significantly induces IL-4, IL-5 and IL-13 and inhibits IL-12 and IFN γ synthesis, and induces cell differentiation with over 7 times the activity of retinoic acid in vitro .
References
Bernard et al. (1992), Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor gamma; Biochem. Biophys. Res. Commun. 186 977
Safonova et al. (1994), Fatty acids and retinoids act synergistically on adipose cell differentiation; Biochem. Biophys. Res. Commun. 204 498
Shibuyua et al. (2005), Retinoic acid is a potential negative regulator for differentiation of human periodontal ligament cells; J. Periodontal Res. 40 432
Araoka et al. (2014), Efficient and rapid induction of human iPSCs/ESCs into nephrogenic intermediate mesoderm using small molecule-based differentiation methods; PLoS One. 9 e84881
Oikawa et al. (1993), Three novel synthetic retinoids, Re 80, Am 580 and Am 80, all exhibit anti-angiogenic activity in vivo; Eur. J. Pharmacol.249 113
Gianni et al. (1996), AM580, s stable benzoic acid derivative of retinoic acid has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells; Blood 87 1520
