71441-28-6 Usage
Description
TTNPB (Arotinoid Acid) is a potent synthetic retinoid that acts as a selective agonist for the retinoic acid receptors (RAR). It is an analog of retinoic acid, which selectively activates RAR with high potency and specificity. TTNPB (Arotinoid Acid) is characterized by its ability to inhibit the binding of [3H]tRA with low IC50 values for human RARα, β, and γ, making it a valuable tool in studying the role of RAR in various biological processes.
Uses
Used in Research and Development:
TTNPB (Arotinoid Acid) is used as a research tool for studying the action of RAR in diverse processes such as epidermal cell proliferation, embryogenesis, and stem cell differentiation. Its potent and selective activation of RAR makes it an ideal candidate for understanding the molecular mechanisms underlying these processes and for the development of potential therapeutic strategies targeting RAR.
Used in Transcription Assays:
TTNPB (Arotinoid Acid) is utilized as a RAR-agonist in transcriptional assays conducted in 293T cells. These assays help researchers investigate the effects of RAR activation on gene expression and the subsequent cellular responses.
Used in Cell Culture Studies:
TTNPB has been employed as a RAR-agonist in cultured human cord blood CD34+CD38-lincells. This application allows researchers to study the effects of RAR activation on hematopoietic stem cells and progenitor cells, which are crucial for understanding the role of RAR in blood cell development and function.
Biochemical 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.
In vitro
TTNPB 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 vivo
TTNPB (0.25 mg/kg) causes growth inhibition in both MXT-HS and MXT-HI models by inducing cell apoptosis.
DIFFERENTIATION
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.).
Promotes neuronal differentiation in cultured chick caudal neural plate explants (Diez del Corral et al.).
REPROGRAMMING
Enables 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 RESEARCH
Induces the in vitro growth and differentiation to granulocytes of myeloid progenitors isolated from myelodysplastic syndrome (MDS) patients (Fabian et al.).
Biological Activity
Extremely potent analog of retinoic acid, selective for the retinoic acid receptor (RAR) subtype.
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.
Safety Profile
An experimental teratogen. Otherexperimental reproductive effects. When heated todecomposition it emits acrid smoke and irritating fumes.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 71441-28-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,4,4 and 1 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 71441-28:
(7*7)+(6*1)+(5*4)+(4*4)+(3*1)+(2*2)+(1*8)=106
106 % 10 = 6
So 71441-28-6 is a valid CAS Registry Number.
InChI:InChI=1/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+
71441-28-6Relevant articles and documents
Olefin functionalization/isomerization enables stereoselective alkene synthesis
Gutierrez, Osvaldo,Koh, Ming Joo,Liu, Chen-Fei,Martin, Robert T.,Wang, Hongyu,Zhao, Haonan
, p. 674 - 683 (2021/08/06)
Despite tremendous efforts aimed at devising methods for stereoselective alkene synthesis, critical challenges are yet to be addressed. Direct access to a diverse range of 1-aryl(boryl)-1-methyl-functionalized tri- and tetrasubstituted trans alkenes, entities that are prevalent in many important molecules, through a catalytic manifold from readily available α-olefin substrates remains elusive. Here, we demonstrate that catalytic amounts of a non-precious N-heterocyclic carbene–Ni(I) complex in conjunction with a sterically bulky base promote site- and trans-selective union of monosubstituted olefins with a wide array of electrophilic reagents to deliver tri- and tetrasubstituted alkenes in up to 92% yield and >98% regio- and stereoselectivity. The protocol is amenable to the preparation of carbon- and heteroatom-substituted C=C bonds, providing distinct advantages over existing transformations. Utility is highlighted through concise stereoselective synthesis of biologically active compounds. [Figure not available: see fulltext.].
18-20 MEMBER BI-POLYCYCLIC COMPOUNDS
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, (2016/01/16)
The invention relates to 18-20 member bi-polycyclic compounds, methods of making these compounds, and methods of using them in treating hyperproliferative disorders (e.g., cancer) and non-malignant tumors; promoting muscle formation; inhibiting muscle degeneration or the loss of muscle mass or muscle function; and myofibers ex vivo.
Retinoid compounds and their use
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, (2012/11/06)
The invention relates to retinoid compounds of the formula (I): wherein V is a hydrophobic group;W is a non-polyenic linker; andX is a polar group comprising a hydrogen bond donor; or a salt thereof, and to the use of such compounds in the control of cell differentiation.
