ChemicalBook CAS DataBase List 2097381-85-4

2097381-85-4

Name	VH298
CAS	2097381-85-4
Molecular Formula	C27H33N5O4S
MDL Number	MFCD30742947
Molecular Weight	523.65
MOL File	2097381-85-4.mol

Chemical Properties

Boiling point	860.8±65.0 °C(Predicted)
density	1.33±0.1 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
solubility	DMF:30.0(Max Conc. mg/mL);57.29(Max Conc. mM) DMSO:66.42(Max Conc. mg/mL);126.84(Max Conc. mM) Ethanol:60.79(Max Conc. mg/mL);116.09(Max Conc. mM) Ethanol:PBS (pH 7.2) (1:9):0.1(Max Conc. mg/mL);0.19(Max Conc. mM)
form	A crystalline solid
pka	12.28±0.20(Predicted)
color	Off-white to pink
InChIKey	NDVQUNZCNAMROD-RZUBCFFCSA-N
SMILES	C(NCC1=CC=C(C2SC=NC=2C)C=C1)(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](C(C)(C)C)NC(C1(C#N)CC1)=O

Hazard Information

Uses

(2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide is a VHL inhibitors that decreases hypoxia inducible factor-α during hypoxia associated signaling in human cervical cancer, osteosarcoma HeLa and U2OS. cells.

Biological Activity

HIF-1α and hydroxy-HIF-1α levels increased in VH298-treated rFb in a time- and dose-dependent manner. Thirty micromolar VH298 could significantly increase cell proliferation, angiogenesis, and gene expression of type I collagen-α1 (Col1-α1), vascular endothelial growth factor A (VEGF-A), and insulin-like growth factor 1 (IGF-1). The VH298-treated wound had a better healing pattern, activation of HIF-1 signaling, and vascularization. It is is a potent VHL inhibitor that stabilizes HIF-α and elicits a hypoxic response via a different mechan: the the blockade of the VHL: HIF-α protein-protein interaction downstream of HIF-α hydroxylation by PHD enzymes. It engages with high affinity and specificity with VHL as its only primary cellular target, leading to selective on-target accumulation of hydroxylated HIF-α in a concentration- and time-dependent fashion in different cell lines, with subsequent upregulation of HIF-target genes at both mRNA and protein levels[1-2].

storage

Store at -20°C

References

[1] Julianty Frost. “Potent and selective chemical probe of hypoxic signalling downstream of HIF-α hydroxylation via VHL inhibition.” Nature Communications 7 1 (2016).
[2] Shuo Qiu. “Von Hippel-Lindau (VHL) Protein Antagonist VH298 Improves Wound Healing in Streptozotocin-Induced Hyperglycaemic Rats by Activating Hypoxia-Inducible Factor- (HIF-) 1 Signalling.” Journal of Diabetes Research (2019): 1897174.

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