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Merck
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Documentos

A8843

Sigma-Aldrich

AM580

≥98% (HPLC)

Sinónimos:

4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid

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About This Item

Fórmula empírica (notación de Hill):
C22H25NO3
Número de CAS:
102121-60-8
Peso molecular:
351.44
MDL number:
MFCD00673916
UNSPSC Code:
12352200
PubChem Substance ID:
24891374
NACRES:
NA.77

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)

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

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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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
Endocrinologia Experimentalis (2012)
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)
S C Brooks et al.
Blood, 87(1), 227-237 (1996-01-01)
The ability of subtypes of retinoic acid receptors (RARs) and retinoid X receptors (RXRs) singly and in combination to elicit myeloid differentiation, G1/0-specific growth arrest, and retinoblastoma (RB) tumor suppressor protein dephosphorylation was determined in the human myeloblastic leukemia cell
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Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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