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102121-60-8,MFCD00673916
Catalog No.:AA0006LM

102121-60-8 | AM580

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1mg
98%
in stock  
$26.00   $18.00
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10mg
≥98%
in stock  
$172.00   $120.00
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25mg
≥98%
in stock  
$382.00   $267.00
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50mg
in stock  
$702.00   $492.00
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100mg
98% by HPLC
in stock  
$1,270.00   $889.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0006LM
Chemical Name:
AM580
CAS Number:
102121-60-8
Molecular Formula:
C22H25NO3
Molecular Weight:
351.4388
MDL Number:
MFCD00673916
SMILES:
O=C(c1ccc2c(c1)C(C)(C)CCC2(C)C)Nc1ccc(cc1)C(=O)O
NSC Number:
608001
Properties
Computed Properties
 
Complexity:
546  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
3  
XLogP3:
5.4  

Literature

Title: Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor.

Journal: Scientific reports 20140101

Title: Roflumilast enhances the renal protective effects of retinoids in an HIV-1 transgenic mouse model of rapidly progressive renal failure.

Journal: Kidney international 20120501

Title: Can we cure HIV-1-associated nephropathy in transgenic mice?

Journal: Kidney international 20120501

Title: Retinoic acid receptor agonists regulate expression of ATP-binding cassette transporter G1 in macrophages.

Journal: Biochimica et biophysica acta 20120401

Title: Rapid and efficient reprogramming of somatic cells to induced pluripotent stem cells by retinoic acid receptor gamma and liver receptor homolog 1.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20111108

Title: Effect of synthetic ligands of PPAR α, β/δ, γ, RAR, RXR and LXR on the fatty acid composition of phospholipids in mice.

Journal: Lipids 20111101

Title: Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.

Journal: Environmental health perspectives 20110801

Title: Neuregulins are essential for spermatogonial proliferation and meiotic initiation in neonatal mouse testis.

Journal: Development (Cambridge, England) 20110801

Title: Retinoic acid inhibits endometrial cancer cell growth via multiple genomic mechanisms.

Journal: Journal of molecular endocrinology 20110401

Title: Role of the retinoic acid receptor-α in HIV-associated nephropathy.

Journal: Kidney international 20110301

Title: Identification of diaryl ether-based ligands for estrogen-related receptor α as potential antidiabetic agents.

Journal: Journal of medicinal chemistry 20110210

Title: Novel retinoic acid receptor alpha agonists for treatment of kidney disease.

Journal: PloS one 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Research resource: transcriptome profiling of genes regulated by RXR and its permissive and nonpermissive partners in differentiating monocyte-derived dendritic cells.

Journal: Molecular endocrinology (Baltimore, Md.) 20101101

Title: Retinoic acid receptor-α signalling antagonizes both intracellular and extracellular amyloid-β production and prevents neuronal cell death caused by amyloid-β.

Journal: The European journal of neuroscience 20101001

Title: Allele-specific down-regulation of RPTOR expression induced by retinoids contributes to climate adaptations.

Journal: PLoS genetics 20101001

Title: All-trans retinoic acid enhances the transport of phase II metabolites of benzo[a]pyrene by inducing the Breast Cancer Resistance Protein expression in Caco-2 cells.

Journal: Toxicology letters 20100816

Title: Keratins 2 and 4/13 in reconstituted human skin are reciprocally regulated by retinoids binding to nuclear receptor RARalpha.

Journal: Experimental dermatology 20100701

Title: Mechanism of inhibition of MMTV-neu and MMTV-wnt1 induced mammary oncogenesis by RARalpha agonist AM580.

Journal: Oncogene 20100624

Title: Acidic retinoids synergize with vitamin A to enhance retinol uptake and STRA6, LRAT, and CYP26B1 expression in neonatal lung.

Journal: Journal of lipid research 20100201

Title: Synthesis and pharmacological characterization of Disila-AM80 (Disila-tamibarotene) and Disila-AM580, silicon analogues of the RARalpha-selective retinoid agonists AM80 (Tamibarotene) and AM580.

Journal: ChemMedChem 20091101

Title: Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands.

Journal: Journal of medicinal chemistry 20090326

Title: Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.

Journal: Bioorganic & medicinal chemistry letters 20090115

Title: Experimental effect of retinoic acids on apoptosis during the development of diabetic retinopathy.

Journal: Clinical ophthalmology (Auckland, N.Z.) 20080301

Title: Expression of retinoic acid receptors in human endometrial carcinoma.

Journal: Cancer science 20080201

Title: The Retinoic Acid Receptor-alpha mediates human T-cell activation and Th2 cytokine and chemokine production.

Journal: BMC immunology 20080101

Title: Galactomutarotase and other galactose-related genes are rapidly induced by retinoic acid in human myeloid cells.

Journal: Biochemistry 20071225

Title: Apoptotic extinction of germ cells in testes of Cyp26b1 knockout mice.

Journal: Endocrinology 20071001

Title: A widely used retinoic acid receptor antagonist induces peroxisome proliferator-activated receptor-gamma activity.

Journal: Molecular pharmacology 20070501

Title: Inhibitory effects of retinoic acid receptor alpha stimulants on murine cataractogenesis through suppression of deregulated calpains.

Journal: Investigative ophthalmology & visual science 20070501

Title: Retinoic acid regulates CD1d gene expression at the transcriptional level in human and rodent monocytic cells.

Journal: Experimental biology and medicine (Maywood, N.J.) 20070401

Title: Cellular retinoic acid bioavailability determines epithelial integrity: Role of retinoic acid receptor alpha agonists in colitis.

Journal: Molecular pharmacology 20070101

Title: PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells.

Journal: The Journal of experimental medicine 20061002

Title: Epigenetic silencing of occludin promotes tumorigenic and metastatic properties of cancer cells via modulations of unique sets of apoptosis-associated genes.

Journal: Cancer research 20060915

Title: Retinoic acid improves a hybridoma culture in a fructose-based medium by up-regulation of fructose incorporation via retinoid nuclear receptors.

Journal: Bioscience, biotechnology, and biochemistry 20060901

Title: Retinoic acid exerts dual regulatory actions on the expression and nuclear localization of interferon regulatory factor-1.

Journal: Experimental biology and medicine (Maywood, N.J.) 20060501

Title: Retinoic acid-induced CD38 expression in HL-60 myeloblastic leukemia cells regulates cell differentiation or viability depending on expression levels.

Journal: Journal of cellular biochemistry 20060415

Title: Retinoic acid induces p27Kip1 nuclear accumulation by modulating its phosphorylation.

Journal: Cancer research 20060415

Title: Telomerase targeting by retinoids in cells from patients with myeloid leukemias of various subtypes, not only APL.

Journal: Leukemia 20060401

Title: Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.

Journal: Journal of cellular biochemistry 20060201

Title: Retinoic acid amplifies the host immune response to LPS through increased T lymphocytes number and LPS binding protein expression.

Journal: Molecular and cellular endocrinology 20051221

Title: Discovery of a potent, orally available, and isoform-selective retinoic acid beta2 receptor agonist.

Journal: Journal of medicinal chemistry 20051201

Title: Retinoic acid is a potential negative regulator for differentiation of human periodontal ligament cells.

Journal: Journal of periodontal research 20051201

Title: Physiological and receptor-selective retinoids modulate interferon gamma signaling by increasing the expression, nuclear localization, and functional activity of interferon regulatory factor-1.

Journal: The Journal of biological chemistry 20051028

Title: Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.

Journal: Molecular endocrinology (Baltimore, Md.) 20051001

Title: Expression of the retinoic acid-metabolizing enzyme CYP26A1 limits programmed cell death.

Journal: Molecular pharmacology 20050501

Title: Implication of Wt1 in the pathogenesis of nephrogenic failure in a mouse model of retinoic acid-induced caudal regression syndrome.

Journal: The American journal of pathology 20050501

Title: A retinoic acid receptor beta/gamma-selective prodrug (tazarotene) plus a retinoid X receptor ligand induces extracellular signal-regulated kinase activation, retinoblastoma hypophosphorylation, G0 arrest, and cell differentiation.

Journal: Molecular pharmacology 20041201

Title: Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands.

Journal: Archives of toxicology 20041101

Title: Survival of activated human T lymphocytes is promoted by retinoic acid via induction of IL-2.

Journal: International immunology 20040301

Title: Modifying effects of 1'-acetoxychavicol acetate (ACA) and the novel synthetic retinoids Re-80, Am-580 and Am-55P in a two-stage carcinogenesis model in female rats.

Journal: Toxicologic pathology 20040101

Title: All-trans retinoic acid modulates microvascular endothelial cell hemostatic properties.

Journal: Haematologica 20030801

Title: Ligation of retinoic acid receptor alpha regulates negative selection of thymocytes by inhibiting both DNA binding of nur77 and synthesis of bim.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030401

Title: Arginine of retinoic acid receptor beta which coordinates with the carboxyl group of retinoic acid functions independent of the amino acid residues responsible for retinoic acid receptor subtype ligand specificity.

Journal: Archives of biochemistry and biophysics 20030115

Title: RAR agonists stimulate SOX9 gene expression in breast cancer cell lines: evidence for a role in retinoid-mediated growth inhibition.

Journal: Oncogene 20021107

Title: Synthesis and biological activity of retinoic acid receptor-alpha specific amides.

Journal: Bioorganic & medicinal chemistry letters 20021104

Title: Enhancement of the inducible NO synthase activation by retinoic acid is mimicked by RARalpha agonist in vivo.

Journal: American journal of physiology. Endocrinology and metabolism 20020901

Title: Effects of retinoic acid receptor-selective agonists on human nasal epithelial cell differentiation.

Journal: American journal of respiratory cell and molecular biology 20011201

Title: Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells.

Journal: Biochimica et biophysica acta 20011031

Title: Retinoids inhibit the actions of angiotensin II on vascular smooth muscle cells.

Journal: Circulation research 20010330

Title: Synergistic teratogenic effects induced by retinoids in mice by coadministration of a RARalpha- or RARgamma-selective agonist with a RXR-selective agonist.

Journal: Toxicology and applied pharmacology 20010101

Title: Effects of retinoids on in vitro and in vivo IgE production.

Journal: International archives of allergy and immunology 20010101

Title: In silico discovery of novel retinoic acid receptor agonist structures.

Journal: BMC structural biology 20010101

Title: Induction of the cytochrome P450 gene CYP26 during mucous cell differentiation of normal human tracheobronchial epithelial cells.

Journal: Molecular pharmacology 20000901

Title: Retinoic acid is a negative regulator for the differentiation of cord blood-derived human mast cell progenitors.

Journal: Blood 20000501

Title: The role of specific retinoid receptors in sebocyte growth and differentiation in culture.

Journal: The Journal of investigative dermatology 20000201

Title: Evidence for the involvement of both retinoic acid receptor- and retinoic X receptor-dependent signaling pathways in the induction of tissue transglutaminase and apoptosis in the human myeloma cell line RPMI 8226.

Journal: Blood 19980401

Title: Selective high affinity retinoic acid receptor alpha or beta-gamma ligands.

Journal: Molecular pharmacology 19911001

Title: Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.

Journal: Journal of medicinal chemistry 19881101

Title: New benzoic acid derivatives with retinoid activity: lack of direct correlation between biological activity and binding to cellular retinoic acid binding protein.

Journal: Cancer research 19870701

Title: Purification and properties of polyol dehydrogenase from Cephalosporium chrysogenus.

Journal: Journal of bacteriology 19760101

Title: Gianní M, et al. AM580, a stable benzoic derivative of retinoic acid, has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells. Blood. 1996 Feb 15;87(4):1520-31.

Title: Lu Y, et al. Mechanism of inhibition of MMTV-neu and MMTV-wnt1 induced mammary oncogenesis by RARalpha agonist AM580. Oncogene. 2010 Jun 24;29(25):3665-76.

Title: Bosch A, et al. Reversal by RARα agonist Am580 of c-Myc-induced imbalance in RARα/RARγ expression during MMTV-Myc tumorigenesis. Breast Cancer Res. 2012 Aug 24;14(4):R121.

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