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SML2034

Sigma-Aldrich

AGN 193109

≥98% (HPLC)

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Synonym(s):
4-[2-[5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl]ethynyl]-benzoic acid, AGN193109, CD 3106
Empirical Formula (Hill Notation):
C28H24O2
CAS Number:
Molecular Weight:
392.49
MDL number:
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

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1 of 4

This Item
SML2665SML0805SML1149
vibrant-m

SML2034

AGN 193109

vibrant-m

SML2665

AGN194310

vibrant-m

SML0805

CID16020046

vibrant-m

SML1149

BMS-189453

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

solubility

DMSO: 2 mg/mL, clear (warmed)

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 1 mg/mL, clear (warmed)

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

color

white to beige

color

white to beige

color

white to beige

color

white to beige

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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D R Soprano et al.
Toxicology and applied pharmacology, 174(2), 153-159 (2001-07-12)
The synthetic retinoid AGN 193109 is a potent pan retinoic acid receptor (RAR) antagonist. Treatment of pregnant mice with a single oral 1 mg/kg dose of this antagonist on day 8 postcoitum results in severe craniofacial (median cleft face or
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
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
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

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