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SML0573

Sigma-Aldrich

Ro 41-5253

≥98% (HPLC)

Synonym(s):

4-(2-(7-(Heptyloxy)-3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)-1-propenyl)-Benzoic acid, S,S-dioxide, 4-[(1E)-2-[7-(Heptyloxy)-3,4-dihydro-4,4-dimethyl-1,1-dioxido-2H-1-benzothiopyran-6-yl]-1-propen-1-yl]-benzoic acid, 4-[2-(7-Heptoxy-4,4-dimethyl-1,1-dioxo-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoic acid, GR110, LG-629, RO 415253, Ro41-5253

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About This Item

Empirical Formula (Hill Notation):
C28H36O5S
CAS Number:
144092-31-9
Molecular Weight:
484.65
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

InChI

1S/C28H36O5S/c1-5-6-7-8-9-15-33-25-19-26-24(28(3,4)14-16-34(26,31)32)18-23(25)20(2)17-21-10-12-22(13-11-21)27(29)30/h10-13,17-19H,5-9,14-16H2,1-4H3,(H,29,30)/b20-17+

InChI key

JEIWQRITHXYGIF-LVZFUZTISA-N

Application

Ro 41-5253 has been used as a retinoic acid receptor-α (RAR-α) antagonist to study its effect on hepatitis B virus (HBV) infection.

Biochem/physiol Actions

Ro 41-5253 ( GR110) is a potent (IC50 = 16 nM) and selective retinoic acid receptor-α (RARα) antagonist, with some recently discovered activity as a PPARγ agonist at 50-fold higher concentrations (EC50 = 810 nM). Ro 41-5253 inhibited differentiation and prevented the loss of human HSCs that otherwise occurs in short-term culture.
Ro 41-5253 is a member of an interesting class of retinoids with anti-proliferative properties. It can repress the activity of retinoic acid receptor-α (RAR-α) in rat embryonic gonad culture. Ro 41-5253 can decrease the expression stimulated by the retinoic acid gene 8 (STRA8) gene. It can prevent multiplication and stimulate apoptosis in breast cancer cell lines.

Features and Benefits

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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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T Scantlebury et al.
The Biochemical journal, 356(Pt 2), 445-452 (2001-05-23)
Acylation-stimulating protein (ASP), a product of complement C3, stimulates triacylglycerol synthesis in adipocytes. Previous studies have identified transthyretin, associated with chylomicrons, as a stimulator of C3 and ASP production. Since both transthyretin and chylomicrons transport retinyl ester/retinol, our goal was
Jun-ichi Nagai et al.
Cancer research, 64(21), 7910-7917 (2004-11-03)
To seek a novel therapeutic approach to neuroblastoma (NBL), we used three NBL cell lines (SK-N-DZ, NH12, and SK-N-SH) to examine the underlining molecular mechanisms of cellular reactions and sensitivity to all-trans-retinoic acid (ATRA). SK-N-DZ cells expressed relatively high levels
Ingo Stuckmann et al.
Developmental biology, 255(2), 334-349 (2003-03-22)
We have established a heart slice primary culture, which allows us to mechanically separate distinct cardiac cell populations and assay their relative mitogenic and trophic effects on cardiac myocyte proliferation and survival. Using this system, we have found that a
Vanmathy R Kasimanickam et al.
Theriogenology, 79(1), 10-16 (2012-10-30)
Retinoic acid (RA) is an essential component for development and maintenance of the male genital tract and for spermatogenesis. Aldehyde dehydrogenase (ALDH)1, cytochrome P450 (CYP)26b1, RA receptor (RAR)α, cellular RA-binding protein (CRAB)II, and stimulated by RA gene (STRA)8 are involved
N Bhattacharyya et al.
Molecular and cellular biology, 17(11), 6481-6490 (1997-10-29)
Transcription of the retinoic acid receptor beta2 (RARbeta2) gene is induced by retinoic acid (RA) in mouse P19 embryonal carcinoma (EC) cells. Here we studied RA-induced chromatin structure alterations in the endogenous RARbeta2 promoter and in an integrated, multicopy RARbeta2
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