Thalidomide

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Cat.No. 0652 - Thalidomide | C13H10N2O4 | CAS No. 50-35-1
Description: Binds cereblon, inhibiting ubiquitin ligase activity; alsoTNF-a synthesis inhibitor
Chemical Name: N-(2,6-dioxo-3-piperidinyl)phthalimide
Purity: ≥99% (HPLC)
Datasheet
Citations (11)
Reviews
Literature

Biological Activity

Selective inhibitor of tumor necrosis factor α (TNF-α) synthesis. Also binds cereblon, inhibiting ubiquitin ligase activity. Teratogen, sedative-hypnotic with inherent anti-inflammatory properties. Promotes degradation of transcription factor SALL4.

Technical Data

M. Wt 258.23
Formula C13H10N2O4
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 50-35-1
PubChem ID 5426
InChI Key UEJJHQNACJXSKW-UHFFFAOYSA-N
Smiles O=C1N(C2CCC(=O)NC2=O)C(=O)C2=C1C=CC=C2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 6.46 25

Preparing Stock Solutions

The following data is based on the product molecular weight 258.23. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.25 mM 15.49 mL 77.45 mL 154.9 mL
1.25 mM 3.1 mL 15.49 mL 30.98 mL
2.5 mM 1.55 mL 7.75 mL 15.49 mL
12.5 mM 0.31 mL 1.55 mL 3.1 mL

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References

References are publications that support the biological activity of the product.

Boireau et al (1997) Thalidomide reduces MPTP-induced decrease in striatal dopamine levels in mice. Neurosci.Lett. 234 123 PMID: 9364513

Kanbayashi et al (1996) Thalidomide, a hypnotic with immune modulating properties, increases cataplexy in canine narcolepsy. Neuroreport 7 1881 PMID: 8905685

Makonkawkeyoon et al (1993) Thalidomide inhibits the replication of human-immunodeficiency-virus type 1. Proc.Natl.Acad.Sci.U.S.A. 90 5974 PMID: 8327469

Zhang et al (2008) Thalidomide influences growth and vasculogenic mimicry channel formation in melanoma. J.Exp.Clin.Cancer Res. 27 60 PMID: 18983651

Sampaio et al (1991) Thalidomide selectively inhibits tumor necrosis factor α production by stimulated human monocytes. J.Exp.Med. 173 699 PMID: 1997652

Merck Index 12 9390

Ito et al (2010) Identification of a primary target of thalidomide teratogenicity. Science 327 1345 PMID: 20223979

Donovan et al (2018) Thalidomide promotes degradation of SALL4, a transcription factor implicated in Duane Radial Ray Syndrome. Elife 7 e38430 PMID: 30067223


If you know of a relevant reference for Thalidomide, please let us know.

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Keywords: Thalidomide, Thalidomide supplier, TNF-α, TNF-alpha, synthesis, inhibitors, inhibits, Interleukins, Tumor, Necrosis, Factor-α, Factor-alpha, Cytokines, Signaling, Signalling, teratogen, anti-inflammatory, angiogenesis, cereblon, ubiquitin, E3, ligase, SALL4, Antiangiogenics, Ubiquitin, Ligases, PROTACs, Other, Transcription, Factors, 0652, Tocris Bioscience

⚠ WARNING: This product can expose you to chemicals including Thalidomide, which is known to the State of California to cause reproductive toxicity with developmental effects. For more information, go to www.P65Warnings.ca.gov

11 Citations for Thalidomide

Citations are publications that use Tocris products. Selected citations for Thalidomide include:

Girgis et al (2010) Effect of thalidomide and arsenic trioxide on the release of tumor necrosis factor-α and vascular endothelial growth factor from the KG-1a human acute myelogenous leukemia cell line. MBio 1 663 PMID: 22966360

Ahn et al (2007) Salinosporamide A (NPI-0052) potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through down-modulation of NF-kappaB regulated gene products. Blood 110 2286 PMID: 17609425

Pathak et al (2007) Ursolic acid inhibits STAT3 activation pathway leading to suppression of proliferation and chemosensitization of human multiple myeloma cells. Mol Cancer Res 5 943 PMID: 17855663

Kannappan et al (2010) γ-Tocotrienol but not γ-tocopherol blocks STAT3 cell signaling pathway through induction of protein-tyrosine phosphatase SHP-1 and sensitizes tumor cells to chemotherapeutic agents. J Biol Chem 285 33520 PMID: 20720018

Gu et al (2010) Intraperitoneal injection of thalidomide attenuates bone cancer pain and decreases spinal tumor necrosis factor-α expression in a mouse model. Mol Pain 6 64 PMID: 20923560

Pandey et al (2010) Betulinic acid suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase SHP-1 in human multiple myeloma cells. Int J Cancer 127 282 PMID: 19937797

Sandur et al (2010) 5-hydroxy-2-methyl-1,4-naphthoquinone, a vitamin K3 analogue, suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase, SHP-1: potential role in chemosensitization. Mol Cancer Res 8 107 PMID: 20068065

Rocha et al (2006) Relevance of tumour necrosis factor-alpha for the inflammatory and nociceptive responses evoked by carrageenan in the mouse paw. Br J Pharmacol 148 688 PMID: 16702985

Helmy et al (2015) Additive Renoprotection by Pioglitazone and Fenofibrate against Inflammatory, Oxidative and Apoptotic Manifestations of Cisplatin Nephrotoxicity: Modulation by PPARs. PLoS One 10 e0142303 PMID: 26536032

Eter and Spitznas (2002) DMSO mimics inhibitory effect of thalidomide on choriocapillary endothelial cell proliferation in culture. Oncol Lett 86 1303 PMID: 12386094

Sung et al (2009) Curcumin circumvents chemoresistance in vitro and potentiates the effect of thalidomide and bortezomib against human multiple myeloma in nude mice model. Mol Cancer Ther 8 959 PMID: 19372569


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Literature in this Area

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