4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Chemical Properties

Melting point:

265-267℃

Boiling point:

485.24°C (rough estimate)

Density 

1.154

refractive index 

1.5614 (estimate)

storage temp. 

-20°C

solubility 

Soluble in DMSO (20mg/ml) or ethanol (10mg/ml).

form 

White to off-white solid.

pka

4.28±0.10(Predicted)

color 

Off-white

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

Safety Information

WGK Germany 

3

RTECS 

DH6834890

HS Code 

2924.29.7790

MSDS

• Language:English Provider:SigmaAldrich

4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Usage And Synthesis

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

Retinoid derivative used for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation. AM 580 inhibits tumor proliferation by reducing the level of RARγ and activates RAR β. This receptor increases the expression of disintegrin and metalloprotease.

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 .

storage

Store at RT

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

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