A8843
AM580
≥98% (HPLC), RAR-α agonist, solid
Synonym(s):
4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid
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About This Item
Empirical Formula (Hill Notation):
C22H25NO3
CAS Number:
Molecular Weight:
351.44
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Product Name
AM580, ≥98% (HPLC)
Quality Level
Assay
≥98% (HPLC)
form
solid
storage temp.
−20°C
SMILES string
CC1(C)CCC(C)(C)c2cc(ccc12)C(=O)Nc3ccc(cc3)C(O)=O
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)
InChI key
SZWKGOZKRMMLAJ-UHFFFAOYSA-N
Gene Information
human ... RARA(5914), RARB(5915)
Related Categories
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.
Application
Retinoid derivative used for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Marie Virtanen et al.
Experimental dermatology, 19(7), 674-681 (2010-05-12)
Disorders of keratinization are often treated with vitamin A derivatives (retinoids) which affect keratinocyte differentiation, including keratin (KRT) gene expression. In vivo, suprabasal keratinocytes normally express only keratin (K) 1, K2 and K10, but after topical application of all-trans retinoic
Synthesis and pharmacological characterization of Disila-AM80 (Disila-tamibarotene) and Disila-AM580, silicon analogues of the RARalpha-selective retinoid agonists AM80 (Tamibarotene) and AM580.
Reinhold Tacke et al.
ChemMedChem, 4(11), 1797-1802 (2009-10-01)
Yasmeen G Ghnewa et al.
Clinical immunology (Orlando, Fla.), 183, 91-98 (2017-08-07)
Invariant natural killer T (iNKT) cells are cytotoxic T cells that respond to glycolipid antigens presented by CD1d. Therapeutic activation of iNKT cells with α-galactosylceramide (α-GalCer) can prevent and reverse tumor growth in mice and clinical trials involving α-GalCer-stimulated iNKT
You-Hong Cheng et al.
Journal of molecular endocrinology, 46(2), 139-153 (2011-02-12)
Previous studies have indicated that retinoic acid (RA) may be therapeutic for endometrial cancer. However, the downstream target genes and pathways triggered by ligand-activated RA receptor α (RARα) in endometrial cancer cells are largely unknown. In this study, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
Vitamin A in Health and Disease (2007)
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