A8843

AM580

Name: AM580
Brand: SIGMA
Price: 252 USD
Availability: InStock

≥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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5 MG

$252.00

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₅NO₃

CAS Number:

102121-60-8

Molecular Weight:

351.44

MDL number:

MFCD00673916

UNSPSC Code:

12352200

PubChem Substance ID:

24891374

NACRES:

NA.77

Key Documents

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Product Name

AM580, ≥98% (HPLC)

Quality Level

200

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

Bioactive Small Molecule Agonists

Bioactive Small Molecules

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Show Differences

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This Item	SML1070	SML0771	T3205
Sigma-Aldrich A8843 AM580	Sigma-Aldrich SML1070 SR-58611A	Sigma-Aldrich SML0771 LG100754	Sigma-Aldrich T3205 Tamibarotene
form solid	form powder	form powder	form powder
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. room temp
Gene Information human ... RARA(5914), RARB(5915)	Gene Information human ... ADRB3(155)	Gene Information -	Gene Information -

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.[1] AM580 suppresses endometrial cancer cell proliferation.[2]

Application

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

Storage Class

11 - Combustible Solids

wgk_germany

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

0000507930

0000500132

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Endocrinologia Experimentalis (2012)

The basic helix-loop-helix transcription factor, heart and neural crest derivatives expressed transcript 2, marks hepatic stellate cells in zebrafish: analysis of stellate cell entry into the developing liver.

Chunyue Yin et al.

Hepatology (Baltimore, Md.), 56(5), 1958-1970 (2012-04-11)

Hepatic stellate cells (HSCs) are liver-specific mesenchymal cells that play vital roles in liver development and injury. Our knowledge of HSC biology is limited by the paucity of in vivo data. HSCs and sinusoidal endothelial cells (SECs) reside in close

Vitamin A in Health and Disease (2007)

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)

Keratins 2 and 4/13 in reconstituted human skin are reciprocally regulated by retinoids binding to nuclear receptor RARalpha.

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

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AM580