4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID
- Product Name
- 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID
- CAS No.
- 102121-60-8
- Chemical Name
- 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID
- Synonyms
- cd336;AM 580;CS-1051;l)amino-;ro40-6055;NSC 608001;AM580 (CD336);AM-580;AM 580;CD336; NSC608001; RO 40-6055;4-(1,1,4,4-Tetramethyltetralin-6-ylcarbonylamino)benzoic acid;4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CA...
- CBNumber
- CB9781234
- Molecular Formula
- C22H25NO3
- Formula Weight
- 351.44
- MOL File
- 102121-60-8.mol
4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Property
- 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
- WGK Germany
- 3
- RTECS
- DH6834890
- HS Code
- 2924.29.7790
N-Bromosuccinimide Price
- Product number
- A8843
- Product name
- AM 580
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $229
- Updated
- 2024/03/01
- Product number
- A3082
- Product name
- AM 580
- Packaging
- 5MG
- Price
- $63
- Updated
- 2024/03/01
- Product number
- A3082
- Product name
- AM 580
- Packaging
- 100MG
- Price
- $516
- Updated
- 2024/03/01
- Product number
- J65155
- Product name
- AM 580
- Packaging
- 10mg
- Price
- $131.65
- Updated
- 2024/03/01
- Product number
- 15261
- Product name
- AM 580
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Chemical Properties,Usage,Production
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
4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Preparation Products And Raw materials
Raw materials
Preparation Products
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