Description In vitro In vivo
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VH298

Description In vitro In vivo
Product Name
VH298
CAS No.
2097381-85-4
Chemical Name
VH298
Synonyms
VH298;VHL-298;CS-2647;VH298;VH 298;VH298 USP/EP/BP;E3 ligase-recruiting Moiety,VH-298,Inhibitor,VH298,Ligands for E3 Ligase,VH 298,inhibit;L-Prolinamide, N-[(1-cyanocyclopropyl)carbonyl]-3-methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-, (4R)-;(2S,4R)-1-((S)-2-(1-cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide;(2S,4R)-1-((S)-2-(1-Cyanocyclopropane-1-carboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide;(2S,4R)-1-[(2S)-2-[(1-cyanocyclopropanecarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide
CBNumber
CB73344894
Molecular Formula
C27H33N5O4S
Formula Weight
523.65
MOL File
2097381-85-4.mol
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VH298 Property

Boiling point:
860.8±65.0 °C(Predicted)
Density 
1.33±0.1 g/cm3(Predicted)
storage temp. 
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
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
21133
Product name
VH298
Purity
≥98%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
21133
Product name
VH298
Purity
≥98%
Packaging
5mg
Price
$98
Updated
2024/03/01
Cayman Chemical
Product number
21133
Product name
VH298
Purity
≥98%
Packaging
10mg
Price
$178
Updated
2024/03/01
Cayman Chemical
Product number
21133
Product name
VH298
Purity
≥98%
Packaging
25mg
Price
$397
Updated
2024/03/01
Tocris
Product number
6156
Product name
VH298
Purity
≥98%(HPLC)
Packaging
10
Price
$244
Updated
2021/12/16
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VH298 Chemical Properties,Usage,Production

Description

VH298 is a potent VHL (Von Hippel-Lindau, the E3 ligase) inhibitor that stabilizes HIF-α. VH298 blocks the VHL:HIF-α interaction with Kd of 90 nM in isothermal titration calorimetry (ITC) and 80 nM in a competitive fluorescence polarization assay. VH-298 can be used in PROTAC technology.

In vitro

VH298 can activate the HIF-1 signalling pathway by stabilizing both forms of HIF-1α in vitro. VH298 promotes rFb variability, migration, and synthesis of collagen and regulatory cell factors. VH298 improves the angiogenesis of hUVEC.

In vivo

VH298 can activate the HIF-1 signalling pathway by stabilizing both forms of HIF-1α in vitro. VH298 promotes rFb variability, migration, and synthesis of collagen and regulatory cell factors. VH298 improves the angiogenesis of hUVEC.

Description

VH-298 is a E3 ligase ligand-linker conjugate that couples the VHL ligand and blocks the interaction between VHL and HIF-α, initiating hypoxic response.

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.

VH298 Preparation Products And Raw materials

Raw materials

Preparation Products

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VH298 Suppliers

Tocris Bioscience
Tel
--
Fax
--
Email
customerservice@tocris.co.uk
Country
United Kingdom
ProdList
5726
Advantage
77
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View Lastest Price from VH298 manufacturers

Hubei Chuchang Biotech Co., Ltd.
Product
VH-298 2097381-85-4
Price
US $0.00-0.00/MG
Min. Order
1MG
Purity
98%+ HPLC HNMR
Supply Ability
50 g per month
Release date
2024-03-29
Career Henan Chemical Co
Product
VH298 2097381-85-4
Price
US $1.00/kg
Min. Order
1kg
Purity
95%-99%
Supply Ability
100kg
Release date
2018-12-24

2097381-85-4, VH298Related Search:


  • VH298
  • VH298;VH 298
  • CS-2647
  • (2S,4R)-1-((S)-2-(1-cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
  • VH298 USP/EP/BP
  • (2S,4R)-1-[(2S)-2-[(1-cyanocyclopropanecarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide
  • (2S,4R)-1-((S)-2-(1-Cyanocyclopropane-1-carboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
  • E3 ligase-recruiting Moiety,VH-298,Inhibitor,VH298,Ligands for E3 Ligase,VH 298,inhibit
  • L-Prolinamide, N-[(1-cyanocyclopropyl)carbonyl]-3-methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-, (4R)-
  • VHL-298
  • 2097381-85-4