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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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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
The antiproliferative effects of melatonin on experimental pituitary and colonic tumors. Possible involvement of the putative nuclear binding site?
M Pawlikowski et al.
Advances in experimental medicine and biology, 460, 369-372 (2000-05-16)
L Li et al.
Life sciences, 65(10), 1067-1076 (1999-09-28)
Stimulation of rat epididymal epithelial cell proliferation by melatonin was demonstrated by thymidine incorporation and flow cytometric analyses. The stimulatory effect of melatonin was dependent on the hormone concentration and the duration of cell exposure to the hormone. Maximal stimulation
S García-Mauriño et al.
Journal of pineal research, 29(3), 129-137 (2000-10-18)
The report shows that melatonin enhances IL-2 and IL-6 production by two human lymphocytic (Jurkat) and monocytic (U937) cell lines via a nuclear receptor-mediated mechanism. Jurkat cells express nuclear (RZRalpha, RORalpha1 and RORalpha2) and membrane (mt1) melatonin receptors, and melatonin
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
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