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SML2034

Sigma-Aldrich

AGN 193109

≥98% (HPLC)

Synonym(s):

4-[2-[5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl]ethynyl]-benzoic acid, AGN193109, CD 3106

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About This Item

Empirical Formula (Hill Notation):
C28H24O2
CAS Number:
171746-21-7
Molecular Weight:
392.49
MDL number:
MFCD00943817
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O=C(O)C1=CC=C(C#CC2=CC=C3C(C)(C)CC=C(C4=CC=C(C)C=C4)C3=C2)C=C1

InChI

1S/C28H24O2/c1-19-4-11-22(12-5-19)24-16-17-28(2,3)26-15-10-21(18-25(24)26)7-6-20-8-13-23(14-9-20)27(29)30/h4-5,8-16,18H,17H2,1-3H3,(H,29,30)

InChI key

NCEQLLNVRRTCKJ-UHFFFAOYSA-N

Biochem/physiol Actions

AGN 193109 is an orally active retinoic acid receptor (RAR) antagonist that targets all three RAR subtypes with higher affinity (RARα/β/γ Kd = 2 nM) than all-trans retinoic acid/ATRA (RARα/β/γ Kd = 9/12/19 nM). AGN 193109 potently antagonizes against ATRA-induced transcription in RARα, RARβ, and RARγ transfected CV-1 cells (by 85%, 62%, and 100%, respectively, by equal molar AGN 193109 against ATRA). AGN 193109 is also widely employeed to block RAR-mediated physiological and pathalogical processes in mice and rats in vivo via oral (1-10 mg/kg) or topical (0.3-36 μmol/kg) administration.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Shriram Nallamshetty et al.
Bone, 67, 281-291 (2014-07-30)
PPARγ, a ligand-activated nuclear receptor, regulates fundamental aspects of bone homeostasis and skeletal remodeling. PPARγ-activating anti-diabetic thiazolidinediones in clinical use promote marrow adiposity, bone loss, and skeletal fractures. As such, delineating novel regulatory pathways that modulate the action of PPARγ
Quan Wu et al.
PLoS biology, 14(9), e1002553-e1002553 (2016-09-09)
The differential programming of sperm and eggs in gonads is a fundamental topic in reproductive biology. Although the sexual fate of germ cells is believed to be determined by signaling factors from sexually differentiated somatic cells in fetal gonads, the
Emmanuelle Gruz-Gibelli et al.
Neural plasticity, 2016, 3707406-3707406 (2016-02-18)
The amyloid-β peptide or Aβ is the key player in the amyloid-cascade hypothesis of Alzheimer's disease. Aβ appears to trigger cell death but also production of double-strand breaks (DSBs) in aging and Alzheimer's disease. All-trans retinoic acid (RA), a derivative
D M Kochhar et al.
The International journal of developmental biology, 42(4), 601-608 (1998-08-07)
Multiple fetal anomalies occur in vitamin A deficient animals as well as in retinoic acid receptor gene 'knockout' mice, indicating that retinoic acid (an active metabolite of vitamin A) performs some essential functions in normal development. Additional approaches are needed
A M Standeven et al.
Toxicology and applied pharmacology, 138(1), 169-175 (1996-05-01)
AGN 193109 was recently identified as a potent retinoic acid receptor (RAR) antagonist in vitro. The purpose of the present study was to determine if AGN 193109 functions as an RAR antagonist in vivo and thus could prevent and/or treat
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