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| 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Basic information |
| Product Name: | 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID | | Synonyms: | AM 580;4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID;2-Naphthalenecarboxamide,5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-N-3-quinolinyl-;Benzoic acid,4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]-;4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamido)benzoic acid;4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl)aminobenz;4-(1,1,4,4-Tetramethyltetralin-6-ylcarbonylamino)benzoic acid;4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-ylcarbonylamino)benzoic acid | | CAS: | 102121-60-8 | | MF: | C22H25NO3 | | MW: | 351.44 | | EINECS: | | Product Categories: | Intracellular receptor | | Mol File: | 102121-60-8.mol |
| 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. |
| WGK Germany | 3 | | RTECS | DH6834890 |
| 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 . | | 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 |
| 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Preparation Products And Raw materials |
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![4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID](/img/102121-60-8.jpg "4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID")
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