102121-60-8 Usage
Description
4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID, also known as AM-580, is a retinoic acid analog and a selective RARα (retinoic acid receptor-α) agonist. It is a retinobenzoic 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. AM-580 exhibits various biological activities, including inducing or blocking differentiation depending on cell type and environment, and suppressing endometrial cancer cell proliferation.
Uses
Used in Gene Expression Studies:
4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID is used as a retinoid derivative for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation. It inhibits tumor proliferation by reducing the level of RARγ and activates RAR β, which increases the expression of disintegrin and metalloprotease.
Used in Cancer Treatment:
In the Pharmaceutical Industry, 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID is used as an anti-cancer agent, particularly for the treatment of acute promyelocytic leukemia (APL). It stimulates the maturation of granulocytes in NB4 promyelocytic leukemia cell line and APL blasts, and exhibits anti-angiogenic activity in vivo, inducing differentiation of acute promyelocytic leukemia cells.
Used in Stem Cell Differentiation:
In the Biotechnology Industry, 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID is used as a differentiation agent for human induced pluripotent stem cells (iPSCs). In combination with CHIR-99021, it induces differentiation of iPSCs into intermediate mesoderm with an 80% induction rate in 5 days, which is capable of forming kidney structures.
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
Check Digit Verification of cas no
The CAS Registry Mumber 102121-60-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,2,1,2 and 1 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 102121-60:
(8*1)+(7*0)+(6*2)+(5*1)+(4*2)+(3*1)+(2*6)+(1*0)=48
48 % 10 = 8
So 102121-60-8 is a valid CAS Registry Number.
InChI:InChI=1/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)
102121-60-8Relevant articles and documents
Synthetic method of retinoic acid derivative Am580
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, (2021/03/13)
The invention discloses a synthetic method of retinoic acid derivative Am580, which comprises: stirring a solution of 2, 5-dimethyl hexane-2, 5-diol in concentrated HCl for 30 min, introducing HCl gasinto the system, carrying out a reaction for 3 h, performing stirring until the system becomes a two-phase mixture, performing cooling to a room temperature, performing filtering to obtain a light pink solid, washing the solid with water, performing recrystallizing in methanol, and performing filtering to obtain an intermediate 3 which is a white solid; dissolving 2, 5-dichloro-2, 5-dimethylhexane in an organic solvent, adding AlCl3 into the solution according to a molar ratio of the 2, 5-dichloro-2, 5-dimethylhexane to the AlCl3 of 1: 0.1-1: 0.2, performing heating to 100-120 DEG C, performing stirring for 16 hours, quenching the reaction by using 3M HCl, performing extracting by using normal hexane, and performing distilling under reduced pressure to remove the solvent to obtain a colorless oily matter intermediate 4. The method has the beneficial effects that the yield of each step is relatively high, the post-treatment is simple, and the industrial production is easier; reaction conditions and a solvent system are optimized for the Friedel-Crafts reaction and the oxidation reaction, and industrial production is better facilitated.
Tricyclic hydroxamate and benzaminde derivatives, compositions and methods
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Page/Page column 13-14; 37, (2008/06/13)
The present invention relates to compounds and methods for inhibiting histone deacetylase enzymatic activity. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit histone deacetylases (HDACs), and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, and also central nervous system diseases. It further deals with processes for preparing said compounds.
Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Amides with Retinoidal Activity
Kagechika, Hiroyuki,Kawachi, Emiko,Hashimoto, Yuichi,Himi, Toshiyuki,Shudo, Koichi
, p. 2182 - 2192 (2007/10/02)
Two types of aromatic amides, terephthalic monoanilides and (arylcarboxamido)benzoic acids, have been shown to possess potent retinoidal activities and can be classified as retinoids.The structure-activity relationships of these amides are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.In generic formula 4 (X = NHCO or CONH), the necessary factors to elicit the retinoidal activities are a medium-sized alkyl group (isopropyl, tert-butyl, etc.) at the meta position and a carboxyl group at the para position of the other benzene ring.The bonding of the amide structure can be reversed, this moiety apparently having the role of locating the two benzene rings at suitable positions with respect to each other.Substitution at the ring position ortho to the amide group or N-methylation of the amido group caused loss of activity, presumably owing to the resultant change of conformation.It is clear that the mutual orientation of the benzylic methyl group(s) and the carboxyl group and their distance apart are essential factors determining the retinoidal activity.Among the synthesized compounds, 4-benzoic acid (Am80) and 4-benzoic acid (Am580) were several times more active than retinoic acid in the assay.They are structurally related to retinoic acid, as is clear from the biological activity of the hybrid compounds (M2 and R2).
