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T3757

Sigma-Aldrich

TTNPB

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Synonym(s):
4-[(E)-2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid, Arotinoid acid
Empirical Formula (Hill Notation):
C24H28O2
CAS Number:
71441-28-6
Molecular Weight:
348.48
MDL number:
MFCD00673917
PubChem Substance ID:
24278733
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

200

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

Gene Information

human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)

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

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H315 - H319 - H335 - H360

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  5. What other solvent is TTNPB, product T3757, soluble in besides the solvents given in the product listing - chloroform, ethanol and DMSO?

    TTNPB, product T3757, is also soluble in dimethylformamide purged with an inert gas.

  6. How should a solution of TTNPB, product T3757, be stored?

    Following reconstitution a solution of TTNPB, T3757,  should be stored at 4° C.

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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
M S Sheikh et al.
The Journal of biological chemistry, 269(34), 21440-21447 (1994-08-26)
Retinoids mediate their actions via RARs (retinoic acid receptors) and RXRs (retinoid X receptors). Each class of these nuclear retinoid receptors is further subdivided into three species, namely alpha, beta, and gamma. Recent studies demonstrate that estrogen receptor (ER)-positive human
Masakazu Sato et al.
Oncotarget, 8(25), 40935-40945 (2017-04-14)
Cervical reserve cells are epithelial progenitor cells that are pathologically evident as the origin of cervical cancer. Thus, investigating the characteristics of cervical reserve cells could yield insight into the features of cervical cancer stem cells (CSCs). In this study
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
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