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Merck
CN

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:
102121-60-8
Molecular Weight:
351.44
UNSPSC Code:
12352200
PubChem Substance ID:
24891374
NACRES:
NA.77
MDL number:
MFCD00673916

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Product Name

AM580, ≥98% (HPLC)

SMILES string

CC1(C)CCC(C)(C)c2cc(ccc12)C(=O)Nc3ccc(cc3)C(O)=O

InChI key

SZWKGOZKRMMLAJ-UHFFFAOYSA-N

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)

assay

≥98% (HPLC)

form

solid

storage temp.

−20°C

Quality Level

200

Gene Information

human ... RARA(5914), RARB(5915)

Related Categories

Application

Retinoid derivative used for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000510455
0000510455
0000507930
0000507930
0000500132

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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
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)
Vitamin A in Health and Disease (2007)
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