For research use only. Not for therapeutic Use.
Thiohydantoin, also known as 2-Thiohydantoin and NSC 11772, is a potent inhibitors of mutant IDH1. Thiohydantoin can decrease the cellular concentration of D2HG, reduce the levels of histone methylation, and suppress the proliferation of stem-like cancer cells in BT142 glioma with IDH1 R132H mutation. Somatic mutations of isocitrate dehydrogenase 1 (IDH1) at R132 are frequently found in certain cancers such as glioma. With losing the activity of wild-type IDH1, the R132H and R132C mutant proteins can reduce α-ketoglutaric acid (α-KG) to d-2-hydroxyglutaric acid (D2HG).
| Catalog Number | R044996 |
| CAS Number | 503-87-7 |
| Synonyms | 2-Thioxo-4-imidazolidinone; 2-Thio-hydantoin; 4-Oxo-2-thioxoimidazolidine; Imidazolidin-4-one-2-thione; NSC 11772; Thiohydantoin |
| Molecular Formula | C3H4N2OS |
| Purity | ≥95% |
| Storage | Desiccate at RT |
| IUPAC Name | 2-sulfanylideneimidazolidin-4-one |
| InChI | InChI=1S/C3H4N2OS/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7) |
| InChIKey | UGWULZWUXSCWPX-UHFFFAOYSA-N |
| SMILES | C1C(=O)NC(=S)N1 |
| Reference | </br>1:Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases by 2-Thiohydantoin Compounds. Wu F, Jiang H, Zheng B, Kogiso M, Yao Y, Zhou C, Li XN, Song Y.J Med Chem. 2015 Sep 10;58(17):6899-908. doi: 10.1021/acs.jmedchem.5b00684. Epub 2015 Aug 26. PMID: 26280302 Free PMC Article</br>2:Molecular structure (monomeric and dimeric) and hydrogen bonds in 5-benzyl 2-thiohydantoin studied by FT-IR and FT-Raman spectroscopy and DFT calculations. Deval V, Kumar A, Gupta V, Sharma A, Gupta A, Tandon P, Kunimoto KK.Spectrochim Acta A Mol Biomol Spectrosc. 2014 Nov 11;132:15-26. doi: 10.1016/j.saa.2014.04.101. Epub 2014 Apr 30. PMID: 24845873 </br>3:Experimental (FT-IR, FT-Raman, NMR) and theoretical spectroscopic properties of intermolecular hydrogen bonded 1-acetyl-2-thiohydantoin polymorphs. Sharma A, Gupta V, Tandon P, Rawat P, Maeda S, Kunimoto KK.Spectrochim Acta A Mol Biomol Spectrosc. 2012 May;90:141-51. doi: 10.1016/j.saa.2012.01.033. Epub 2012 Jan 26. PMID: 22336046 </br>4:2-Aminoimidazole, glycociamidine and 2-thiohydantoin-marine alkaloids as molecular inspirations for the development of lead structures. Kumar R, Khan S, Chauhan PM.Curr Drug Targets. 2011 Oct;12(11):1689-708. Review. PMID: 21561428 </br>5:5,5-Diphenyl-2-thiohydantoin-N10 (DPTH-N10) suppresses proliferation of cultured colon cancer cell line COLO-205 by inhibiting DNA synthesis and activating apoptosis. Lee TS, Chen LC, Liu Y, Wu J, Liang YC, Lee WS.Naunyn Schmiedebergs Arch Pharmacol. 2010 Jul;382(1):43-50. doi: 10.1007/s00210-010-0519-4. Epub 2010 May 7. PMID: 20449574 </br>6:Anti-angiogenic action of 5,5-diphenyl-2-thiohydantoin-N10 (DPTH-N10). Liu Y, Wu J, Ho PY, Chen LC, Chen CT, Liang YC, Cheng CK, Lee WS.Cancer Lett. 2008 Nov 28;271(2):294-305. doi: 10.1016/j.canlet.2008.06.016. Epub 2008 Jul 22. PMID: 18649995 </br>7:Structure and anti-proliferation function of 5,5-diphenyl-2-thiohydantoin (DPTH) derivatives in vascular endothelial cells. Cheng CK, Wu J, Liu Y, Lee TS, Kang SJ, Sheu MT, Lee WS.Vascul Pharmacol. 2008 Feb-Mar;48(2-3):138-42. doi: 10.1016/j.vph.2008.01.007. Epub 2008 Feb 7. PMID: 18295547 </br>8:Expedient Lewis acid catalyzed synthesis of a 3-substituted 5-arylidene-1-methyl-2-thiohydantoin Library. Gregg BT, Golden KC, Quinn JF, Tymoshenko DO, Earley WG, Maynard DA, Razzano DA, Rennells WM, Butcher J.J Comb Chem. 2007 Nov-Dec;9(6):1036-40. Epub 2007 Sep 15. PMID: 17867645 </br>9:Modification of intracellular free calcium in cultured F2408 embryo fibroblasts by 3-substituted-2-thiohydantoin derivatives. Incesu Z, Benkli K, Akalin G, Kaplancikli ZA.Cell Biol Int. 2004;28(4):267-72. PMID: 15109982 </br>10:Anti-proliferation effect of 5,5-diphenyl-2-thiohydantoin (DPTH) in human vascular endothelial cells. Shih CR, Wu J, Liu Y, Liang YC, Lin SY, Sheu MT, Lee WS.Biochem Pharmacol. 2004 Jan 1;67(1):67-75. PMID: 14667929 |
