TTNPB (Arotinoid Acid)

TTNPB (Arotinoid Acid) Basic information
Description Uses Biochemical Actions In vitro In vivo DIFFERENTIATION REPROGRAMMING CANCER RESEARCH
Product Name:TTNPB (Arotinoid Acid)
Synonyms:(E)-4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl)benzoic acid;(E)-4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid;RO 13-7410;TTNPB;(e)-openyl);6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-(e)-4-(2-(;(E)-4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)-1-propenyl) benzoic acid;4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthenyl)-1E-propen-1-yl)benzoic acid
CAS:71441-28-6
MF:C24H28O2
MW:348.48
EINECS:
Product Categories:Inhibitors;pharmaceuticam intermediate;Intracellular receptor
Mol File:71441-28-6.mol
TTNPB (Arotinoid Acid) Structure
TTNPB (Arotinoid Acid) Chemical Properties
Melting point 242 °C
Boiling point 422.83°C (rough estimate)
density 1.0932 (rough estimate)
refractive index 1.4480 (estimate)
storage temp. -20°C
solubility chloroform/methanol: soluble9.80 - 10.20 mg/mL, clear, colorless to light yellow
form White solid
pka4.28±0.10(Predicted)
color White to Almost white
InChIKeyFOIVPCKZDPCJJY-JQIJEIRASA-N
CAS DataBase Reference71441-28-6
Safety Information
Hazard Codes T
Risk Statements 60-61-36/37/38
Safety Statements 53-26-36/37/39-45
WGK Germany 3
RTECS DH6834900
HS Code 2916.39.7900
MSDS Information
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SigmaAldrich English
TTNPB (Arotinoid Acid) Usage And Synthesis
DescriptionTTNPB (Arotinoid Acid) is a potent RAR agonist, and inhibits binding of [3H]tRA with IC50 of 5.1 nM, 4.5 nM, and 9.3 nM for human RARα, β, and γ, respectively.
Uses
  1. TTNPB is an analog of retinoic acid that potently and selectively activates retinoic acid receptors (RAR; EC50 = 21, 4, and 2.4 nM for RARα, RARβ, and RARγ, respectively; Beard et al.; Wong et al.).
  2. TTNPB has been used for transcriptional assays in 293T cells. It has also been used as a RAR-agonist in cultured human cord blood CD34+CD38-lin- cells.
  3. It does not act on retinoid X receptors and weakly agonizes farnesoid X receptor (EC50 > 1 µM).
  4. TTNPB is used to study RAR action in diverse processes, including epidermal cell proliferation, embryogenesis, and stem cell differentiation.
Biochemical ActionsSelective 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.
In vitroTTNPB binds to nuclear retinoic acid receptors with high affinity, inhibits binding of [3H]tRA with IC50 of 3.8 nM, 4.0 nM, and 4.5 nM for mRARα, β, and γ, respectively. TTNPB increases transcriptional activation of Mouse RARs in JEG-3 cells after 72 h using conditioned media with EC50 of 2.0 nM, 1.1 nM and 0.8 nM for mRARα, β, and γ, respectively. TTNPB inhibits the growth of normal human mammary epithelial cells (HMECs) and estrogen receptor-positive (ER-positive) breast cancer cells by inducing G1 cell cycle blockade.  TTNPB causes a concentration-dependent decrease in ES-D3 cell differentiation.
In vivoTTNPB (0.25 mg/kg) causes growth inhibition in both MXT-HS and MXT-HI models by inducing cell apoptosis.
DIFFERENTIATION
  1. In combination with CHIR99021 or Activin A, induces intermediate mesoderm formation from human or mouse pluripotent stem cells, respectively (Araoka et al.; Oeda et al.).
  2. Promotes neuronal differentiation in cultured chick caudal neural plate explants (Diez del Corral et al.).
REPROGRAMMINGEnables chemical reprogramming (without genetic factors) of mouse embryonic fibroblasts to induced pluripotent stem (iPS) cells, in combination with CHIR99021, Tranylcypromine, Valproic Acid, 3-Deazaneplanocin A, and E-616452 (Hou et al.).
CANCER RESEARCHInduces the in vitro growth and differentiation to granulocytes of myeloid progenitors isolated from myelodysplastic syndrome (MDS) patients (Fabian et al.).
UsesTTNPB is an analog of retinoic acid that potently and selectively activates retinoic acid receptors.
DefinitionChEBI: A retinoid that consists of benzoic acid substituted at position 4 by a 2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl group. It is a synthetic retinoid that acts as a selective agonist for the retinoic acid receptors (RAR).
Biological ActivityExtremely potent analog of retinoic acid, selective for the retinoic acid receptor (RAR) subtype.
Biochem/physiol ActionsSelective 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.
Safety ProfileAn experimental teratogen. Otherexperimental reproductive effects. When heated todecomposition it emits acrid smoke and irritating fumes.
storageDesiccate at -20°C
references[1] pignatello m a, kauffman f c, levin a a. multiple factors contribute to the toxicity of the aromatic retinoid, ttnpb (ro 13-7410): binding affinities and disposition. toxicology and applied pharmacology, 1997, 142(2): 319-327.
TTNPB (Arotinoid Acid) Preparation Products And Raw materials
Belizatinib TTK21 TTP 22 4-[2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)-benzoicacid Temarotene TRANS-4-STILBENEMETHANOL 4-Vinylbenzoic acid TTNPB (Arotinoid Acid) 1-ISOPROPYL-4-(2-PHENYLVINYL)BENZENE 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene 4,4'-DIMETHYL-TRANS-STILBENE SMR 6 arotinoic methanol SMR 2 4-FORMYL-TRANS-STILBENE methylarotinoid 4-TERT-BUTYLSTYRENE 3-Methyl-TTNPB

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