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C5749

Sigma-Aldrich

CGP 52608

≥98%, solid

Synonym(s):

1-[3-Allyl-4-oxo-thiazolidine-2-ylidene]-4-methyl-thiosemicarbazone, N-Methyl-2-[4-oxo-3-(2-propen-1-yl)-2-thiazolidinylidene]-hydrazinecarbothioamide

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About This Item

Empirical Formula (Hill Notation):
C8H12N4OS2
CAS Number:
87958-67-6
Molecular Weight:
244.34
MDL number:
MFCD00942304
UNSPSC Code:
12352200
PubChem Substance ID:
329775098
NACRES:
NA.77

Assay

≥98%

form

solid

solubility

DMSO: >30 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

CNC(=S)N\N=C1/SCC(=O)N1CC=C

InChI

1S/C8H12N4OS2/c1-3-4-12-6(13)5-15-8(12)11-10-7(14)9-2/h3H,1,4-5H2,2H3,(H2,9,10,14)/b11-8-

InChI key

DDYJDIHOSRTMSE-FLIBITNWSA-N

Application

CGP 52608 has been used as a RAR related orphan receptor α (RORα) synthetic agonist in THP-1 macrophages, in human monocyte cells THP1 and somatic testicular cells.

Biochem/physiol Actions

CGP 52608 is a thiazolidine derivative and an antiarthritic compound. It possesses immunostimulatory functionality and elicits antiproliferative effect in colon tumors. It is cytotoxic towards neural cell lines. CGP 52608 induces apoptosis in tumor and also favors G0-G1 cell cycle phase accumulation in neural cell lines.
CGP 52608 is a specific activator of retinoic acid receptor-related orphan receptor α (RORA).

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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Mercedes M Leon-Blanco et al.
Cancer letters, 216(1), 73-80 (2004-10-27)
The RNA expression levels of human catalytic subunit (TERT) and the RNA subunit (TR) of telomerase were analysed after treatment with the agonists of the membrane receptor (S 20098) and the nuclear receptor (CGP 52608) for melatonin in the MCF-7
M Missbach et al.
The Journal of biological chemistry, 271(23), 13515-13522 (1996-06-07)
Rat adjuvant arthritis is a chronic T cell-dependent autoimmune disease with many similarities to rheumatoid arthritis. We have identified a class of thiazolidine diones with high potency in suppressing chronic inflammation and joint destruction in this experimental model. The lead
I Wiesenberg et al.
Molecular pharmacology, 53(6), 1131-1138 (1998-06-17)
The thiazolidinedione BRL 49653 and the thiazolidinedione derivative CGP 52608 are lead compounds of two pharmacologically different classes of compounds. BRL 49653 is a high affinity ligand of peroxisome proliferator-activated receptor gamma (PPARgamma) and a prototype of novel antidiabetic agents
Cagri Gulec et al.
Experimental cell research, 353(1), 6-15 (2017-02-28)
ROR-alpha is a nuclear receptor, activity of which can be modulated by natural or synthetic ligands. Due to its possible involvement in, and potential therapeutic target for atherosclerosis, we aimed to identify ROR-alpha target genes in monocytic and endothelial cell
Katarzyna Winczyk et al.
Neuro endocrinology letters, 27(3), 351-354 (2006-07-04)
Melatonin may influence directly tumor cells through the specific binding sites. The best known melatonin binding sites are membrane receptors. Recently, the participation of nuclear signalling via estrogen as well as RZR/ROR receptors in oncostatic action of melatonin on the
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