VH 298

Name: VH 298
Brand: Tocris Bioscience
SKU: 6156

Tocris Bioscience, part of Bio-Techne | Catalog # 6156

Citations (7)

COA / SDS

High-affinity inhibitor of VHL

Key Product Details

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)
Molecular Weight:	523.65

View Full Technical Details for VH 298

Technical Data
Citations

Biological Activity for VH 298

VH 298 is a high-affinity inhibitor of E3 ubiquitin ligase VHL (K_d = 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, with similar transcriptional profile to hypoxia. Cell permeable.

Negative control cis VH 298 also available.

Licensing Information

Sold under licence from the University of Dundee

Compound Libraries for VH 298

VH 298 is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen Epigenetics Library. Find out more about compound libraries available from Tocris.

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 for VH 298

M. Wt	523.65
Formula	C₂₇H₃₃N₅O₄S
Storage	Store at -20°C
Purity	≥98% (HPLC)
CAS Number	2097381-85-4
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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility for VH 298

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	52.37	100
	ethanol	52.37	100

Preparing Stock Solutions for VH 298

The following data is based on the product molecular weight 523.65.

Batch specific molecular weights may vary from batch to batch due to the degree 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	19.10 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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References for VH 298

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

Soares 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. 2018 PMID: 28853884
Frost RNA-seq analysis of PHD and VHL inhibitors reveals differences and similarities to the hypoxia response. Wellcome Open Res. 2019 PMID: 30801039
Frost Potent and selective chemical probe of hypoxic signalling downstream of HIF-α hydroxylation via VHL inhibition. Nat.Commun. 2015 PMID: 27811928