Available from stock

5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone

SKU: E0533

Categories:

Synonyms: 10058-F4; 403811-55-2
CAS-Number: C₁₂H₁₁NOS₂
Molecular Formula: 249.35
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (NMR)
Appearance: Yellow to dark yellow powder
Identity: 1H-NMR

Properties

Solvents: DMSO (25 mg/ml), ethanol (5 mg/ml) or water (1 mg/ml).
Density: 1.33 g/mL (predicted)

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H317-H319
Precautionary statements: P280-P305 + P351 + P338
GHS Symbol: GHS07
Transportation: Not dangerous goods

Description: c-Myc is a proto-oncogene that plays an important role in cell proliferation, differentiation, and apoptosis. 5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone [10058-F4] is a cell-permeable thiazolidinone compound that specifically inhibits the c-Myc-Max interaction/dimerization at 64 µM, preventing c-Myc-dependent gene expression and cell proliferation. 10058-F4 inhibits tumor cell growth and proliferation in a c-Myc-dependent manner both in vitro and in vivo. 10058-F4 induces cell-cycle arrest (G0/G1 phase) and apoptosis. 10058-F4 has been found to also upregulate cyclin-dependent kinase (CDK) inhibitors, p21 and p27. In addition to c-Myc, 10058-F4 inhibits the nuclear Myc protein, N-Myc, at 50 µM, inducing arrest, apoptosis, and differentiation in neuroblastoma cells overexpressing the gene for N-Myc. This compound can be used to delineate novel actions of Myc proteins, especially those related to lipid and glucose metabolism. 10058-F4 downregulates human telomerase reverse transcriptase and enhances chemosensitivity in several human cancer cell lines.
Smiles: O=C(NC(S/1)=S)C1=C/C2=CC=C(CC)C=C2
InChi Key: SVXDHPADAXBMFB-JXMROGBWSA-N
References: (1) X. Yin, et al., Oncogene 22, 6151 (2003) , (2) M.J. Huang, et al., Exp. Hematol. 34, 1480 (2006) , (3) C.P. Lin, et al., Anticancer Drugs 18, 161 (2007) , (4) J. Guo, et al., Cancer Chemother. Pharmacol. 63, 615 (2009) , (5) P. Zhang, et al., Mol. Endocrinol. 24, 1274 (2010) , (6) H. Zirath, et al., PNAS 110, 10258 (2013) , (7) M. Zhang, et al., Biomed. Pharmacother. 73, 123 (2015) , (8) M. Lv, et al., Mol. Med. Rep. 18, 421 (2018) , (9) N. Sheikh-Zeineddini, et al., J. Cell Biochem. 120, 14004 (2019) , (10) N. Sheikh-Zeineddini, et al., Eur. J. Pharmacol. 870, 172821 (2020)
InChi: InChI=1S/C12H11NOS2/c1-2-8-3-5-9(6-4-8)7-10-11(14)13-12(15)16-10/h3-7H,2H2,1H3,(H,13,14,15)/b10-7+

c-Myc is a proto-oncogene that plays an important role in cell proliferation, differentiation, and apoptosis. 5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone [10058-F4] is a cell-permeable thiazolidinone compound that specifically inhibits the c-Myc-Max interaction/dimerization at 64 µM, preventing c-Myc-dependent gene expression and cell proliferation. 10058-F4 inhibits tumor cell growth and proliferation in a c-Myc-dependent manner both in vitro and in vivo. 10058-F4 induces cell-cycle arrest (G0/G1 phase) and apoptosis. 10058-F4 has been found to also upregulate cyclin-dependent kinase (CDK) inhibitors, p21 and p27. In addition to c-Myc, 10058-F4 inhibits the nuclear Myc protein, N-Myc, at 50 µM, inducing arrest, apoptosis, and differentiation in neuroblastoma cells overexpressing the gene for N-Myc. This compound can be used to delineate novel actions of Myc proteins, especially those related to lipid and glucose metabolism. 10058-F4 downregulates human telomerase reverse transcriptase and enhances chemosensitivity in several human cancer cell lines.

SKU: E0533

Additional information

Additional information

Synonyms	10058-F4
Purity	≥95% (NMR)
Appearance	Yellow to dark yellow powder
CAS-Number	403811-55-2
Molecular Formula	C12H11NOS2
Molecular Weight	249.35
Identity	1H-NMR
Solvents	DMSO (25 mg/ml), ethanol (5 mg/ml) or water (1 mg/ml).
Density	1.33 g/mL (predicted)
Smiles	O=C(NC(S/1)=S)C1=C/C2=CC=C(CC)C=C2
InChi Key	SVXDHPADAXBMFB-JXMROGBWSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H317-H319
Precautionary statements	P280-P305 + P351 + P338
GHS Symbol	GHS07
Transportation	Not dangerous goods
References	(1) X. Yin, et al., Oncogene 22, 6151 (2003), (2) M.J. Huang, et al., Exp. Hematol. 34, 1480 (2006), (3) C.P. Lin, et al., Anticancer Drugs 18, 161 (2007), (4) J. Guo, et al., Cancer Chemother. Pharmacol. 63, 615 (2009), (5) P. Zhang, et al., Mol. Endocrinol. 24, 1274 (2010), (6) H. Zirath, et al., PNAS 110, 10258 (2013), (7) M. Zhang, et al., Biomed. Pharmacother. 73, 123 (2015), (8) M. Lv, et al., Mol. Med. Rep. 18, 421 (2018), (9) N. Sheikh-Zeineddini, et al., J. Cell Biochem. 120, 14004 (2019), (10) N. Sheikh-Zeineddini, et al., Eur. J. Pharmacol. 870, 172821 (2020)
InChi	InChI=1S/C12H11NOS2/c1-2-8-3-5-9(6-4-8)7-10-11(14)13-12(15)16-10/h3-7H,2H2,1H3,(H,13,14,15)/b10-7+
Quantity	5 mg, 25 mg, Bulk