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Key Documents

SML2034

Sigma-Aldrich

AGN 193109

≥98% (HPLC)

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen


About This Item

Empirický vzorec (Hillův zápis):
C28H24O2
Číslo CAS:
Molekulová hmotnost:
392.49
MDL number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Tadaaki Nakajima et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(50), 14354-14359 (2016-12-03)
The Müllerian duct develops into the oviduct, uterus, and vagina, all of which are quite distinct in their morphology and function. The epithelial fate of these female reproductive organs in developing mice is determined by factors secreted from the stroma;
Synthesis and characterization of a highly potent and effective antagonist of retinoic acid receptors.
A T Johnson et al.
Journal of medicinal chemistry, 38(24), 4764-4767 (1995-11-24)
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
Abhinav Illendula et al.
Oncology reports, 44(3), 1013-1024 (2020-07-25)
Neuroblastoma is the most common inheritable, solid neoplasm in children found under the age of 7 and accounts for approximately 7% of childhood cancers. A common treatment that has been prescribed for over a decade is retinoid therapy [using all‑trans
A T Johnson et al.
Bioorganic & medicinal chemistry letters, 9(4), 573-576 (1999-03-31)
A series of high affinity retinoic acid receptor (RAR) antagonists were prepared based upon the known antagonist AGN 193109 (2). Introduction of various phenyl groups revealed a preference for substitution at the para-position relative to the meta-site. Antagonists with the

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