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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

Quality Level

100

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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P T Ram et al.
Cancer letters, 179(2), 141-150 (2002-03-13)
Two putative melatonin receptors have been described including the cell surface G-protein-linked receptors, mt1 and MT2, and the nuclear retinoic orphan receptor alpha (RORalpha). The mt1 receptor, but not the MT2 receptor, is expressed in human breast tumor cell lines
K Winczyk et al.
Journal of pineal research, 31(2), 179-182 (2001-09-14)
The effects of melatonin and the thiazolinidinedione derivative CGP 52608 on apoptosis of Colon 38 cancer cells were investigated. Male mice were implanted subcutaneously with a suspension of Colon 38 cells. Ten days after induction of tumors, the animals were
M Karasek et al.
Biological signals and receptors, 8(1-2), 75-78 (1999-03-23)
The antiproliferative effects of melatonin and CGP 52608, an exogenous ligand for RZR/ROR receptors, are compared in the present paper. Both compounds exerted similar inhibitory effects on the proliferation of neoplastic cells in mouse colonic adenocarcinoma, DU 145 human prostate
Andrea Balla et al.
Neuropharmacology, 56(5), 915-921 (2009-04-18)
Deficits in N-methyl-D-aspartate receptor (NMDAR)-mediated neurotransmission may underlie dopaminergic hyperactivity in schizophrenia. Dysregulation of the GABAergic system has also been implicated. In this study we investigated a role for GABA(B) receptors as an intermediate step in the pathway leading from
J E Roberts et al.
Journal of pineal research, 28(3), 165-171 (2000-03-30)
Previous work has demonstrated that melatonin inhibits growth of cultured human uveal melanoma cells. The goal of this study was to determine the expression of mRNA encoding the melatonin receptor subtypes and the effect of specific melatonin receptor agonists on
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