VH 298

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Cat.No. 6156 - VH 298 | C27H33N5O4S
Description: High-affinity inhibitor of VHL
Chemical Name: (2S,4R)-1-((S)-2-(1-cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews
Literature

Biological Activity

High-affinity inhibitor of E3 ubiquitin ligase VHL (Kd = 80-90 nM). Blocks interaction between VHL and HIF-α downstream of HIF-α hydroxylation, initiating hypoxic response. Results in time- and concentration-dependent accumulation of hydroxylated HIF-α, and upregulates mRNA and protein levels of HIF target genes. Cell permeable. Negative control cis VH 298 also available.

Licensing Information

Sold under licence from the University of Dundee

External Portal Information

Chemicalprobes.org is a portal that offers independent guidance on the selection and/or application of small molecules for research. The use of VH 298 is reviewed on the Chemical Probes website.

Technical Data

M. Wt 523.65
Formula C27H33N5O4S
Storage Store at -20°C
Purity ≥98% (HPLC)
PubChem ID 122199236
InChI Key NDVQUNZCNAMROD-RZUBCFFCSA-N
Smiles O=C(N[C@@H](C(C)(C)C)C(N1C[C@@H](C[C@H]1C(NCC2=CC=C(C3=C(N=CS3)C)C=C2)=O)O)=O)C4(C#N)CC4

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 52.37 100
ethanol 52.37 100

Preparing Stock Solutions

The following data is based on the product molecular weight 523.65. 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
1 mM 1.91 mL 9.55 mL 19.1 mL
5 mM 0.38 mL 1.91 mL 3.82 mL
10 mM 0.19 mL 0.95 mL 1.91 mL
50 mM 0.04 mL 0.19 mL 0.38 mL

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Product Datasheets

Safety Datasheet

References

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

Frost et al (2015) Potent and selective chemical probe of hypoxic signalling downstream of HIF-α hydroxylation via VHL inhibition. Nat.Commun. 7 13312 PMID: 27811928

Soares et al (2018) Group-based optimization of potent and cell-active inhibitors of the von Hippel-Lindau (VHL) E3 ubiquitin ligase: structure-activity relationships leading to the chemical probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3 J.Med.Chem. 61 599 PMID: 28853884


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View Related Products by Product Action

View all Ubiquitin E3 Ligase Inhibitors

Keywords: VH 298, VH 298 supplier, Inhibitors, Inhibition, VH298, VHL, HIF-alpha, HIF-a, HIF-α, cisVH298, von, Hippel-Lindau, protein, E3, ubiquitin, ligase, Hypoxia, Inducible, Factors, Ubiquitin, Ligases, PROTACs, 6156, Tocris Bioscience

Citations for VH 298

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