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Merck

T3757

Sigma-Aldrich

TTNPB

Sinónimos:

4-[(E)-2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid, Arotinoid acid

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About This Item

Fórmula empírica (notación de Hill):
C24H28O2
Número de CAS:
Peso molecular:
348.48
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

solubility

ethanol: soluble 10 mM
DMSO: soluble 25 mM
chloroform/methanol: soluble 9.80-10.20 mg/mL, clear, colorless to light yellow

Quality Level

storage temp.

−20°C

SMILES string

C\C(=C/c1ccc(cc1)C(O)=O)c2ccc3c(c2)C(C)(C)CCC3(C)C

InChI

1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+

InChI key

FOIVPCKZDPCJJY-JQIJEIRASA-N

Application

TTNPB has been used for transcriptional assays in 293T cells4. It has also been used as a RAR-agonist in cultured human cord blood CD34+CD38-lin- cells5.

Biochem/physiol Actions

Selective and highly potent retinoic acid analog with affinity for retinoic acid receptors (RAR) α, β, and γ, which are nuclear transcription factors. Produces ligand-activated transcription of genes that possess retinoic acid responsive elements.

Features and Benefits

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

TTNPB dissolves in CHCL3/MeOH (1/1) at 9.80 - 10.20 mg/ml to yield a clear, colorless to light yellow solution. It is also soluble at 10 mM in ethanol and at 25 mM in DMSO.

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Olivier M Niemoeller et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 21(1-3), 193-202 (2008-01-23)
Vitamin A and retinoic acid have previously been shown to confer some protection against a severe course of malaria by fostering the phagocytosis of parasitized erythrocytes. Phagocytosis of erythrocytes is stimulated by phosphatidylserine exposure at the cell surface. The present
Matthias W Büttner et al.
Chembiochem : a European journal of chemical biology, 8(14), 1688-1699 (2007-09-05)
Twofold sila-substitution (C/Si exchange) in the saturated ring of the tetrahydronaphthalene skeleton of the retinoid agonists TTNPB (1 a) and 3-methyl-TTNPB (2 a) leads to disila-TTNPB (1 b) and disila-3-methyl-TTNPB (2 b), respectively. The silicon compounds 1 b and 2
Bryan R Haugen et al.
The Journal of clinical endocrinology and metabolism, 89(1), 272-280 (2004-01-13)
Therapy for patients with advanced thyroid carcinoma is limited. Clinical and in vitro studies suggest that some patients with advanced thyroid cancer may respond to therapy with retinoic acid. mRNA expression of the six retinoic acid (RAR) and retinoid X
Karine Hellemans et al.
Hepatology (Baltimore, Md.), 39(1), 97-108 (2004-01-31)
Activation of hepatic stellate cells (HSC) is a central event in the pathogenesis of liver fibrosis during chronic liver injury. We examined the expression of retinoic acid (RAR) and retinoid X receptors (RXR) during HSC activation and evaluated the influence
John S Bertram et al.
Biochimica et biophysica acta, 1740(2), 170-178 (2005-06-14)
Virtually all human tumors are deficient in gap junctional communication (GJC) and the restoration of GJC by forced expression of connexins reduces indices of neoplasia. The expression of connexin 43 (Cx43) is upregulated by cancer-preventive retinoids and carotenoids which correlates

Artículos

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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