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SML2665

Sigma-Aldrich

AGN194310

≥98% (HPLC)

Synonym(s):

4-[2-[4-(4-Ethylphenyl)-2,2-dimethyl-2H-1-benzothiopyran-6-yl]ethynyl]benzoic acid, 4-[[4-(4-Ethylphenyl)-2,2-dimethyl-2H-1-benzothiopyran-6-yl]ethynyl]benzoic acid, AGN 194310, AGN-194310, IRX4310, VTP 194310

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About This Item

Empirical Formula (Hill Notation):
C28H24O2S
CAS Number:
229961-45-9
Molecular Weight:
424.55
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(O)C1=CC=C(C#CC2=CC3=C(SC(C)(C=C3C4=CC=C(CC)C=C4)C)C=C2)C=C1

InChI

1S/C28H24O2S/c1-4-19-7-12-22(13-8-19)25-18-28(2,3)31-26-16-11-21(17-24(25)26)6-5-20-9-14-23(15-10-20)27(29)30/h7-18H,4H2,1-3H3,(H,29,30)

InChI key

LHUPKWKWYWOMSK-UHFFFAOYSA-N

Biochem/physiol Actions

AGN194310 (IRX4310; VTP 194310) is a retinoic acid receptor (RAR) antagonist that targets all three RAR subtypes with higher affinity (RARα/β/γ Kd = 3/2/5 nM) than all-trans retinoic acid/ATRA (RARα/β/γ Kd = 15/13/18 nM) without affecting RXR subtypes. AGN194310 effectively blocks RAR agonist TTNPB-induced transcription activity (using RARα, RARβ, or RARγ transfected cells) and prevents TTNPB toxicity in guinea pigs in vivo (by 79/84/94% at AGN194310/TTNPB ratios of 0.5/2/8). AGN194310 potentiates differentiation in osteoblast cultures (1 μM) and daily oral administration (0.5 mg/kg/d for a10-d period) is reported to cause impaired radial bone growth among 8-wk-old mice.

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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Haider M Hassan et al.
Cell reports, 19(8), 1685-1697 (2017-05-26)
Retinoic acid (RA) plays important roles in development, growth, and homeostasis through regulation of the nuclear receptors for RA (RARs). Herein, we identify Hypermethylated in Cancer 1 (Hic1) as an RA-inducible gene. HIC1 encodes a tumor suppressor, which is often

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