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IOX2(Glycine)

HIF-1α prolyl hydroxylase-2 (PHD2) inhibitor CAS# 931398-72-0

IOX2(Glycine)

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Quality Control of IOX2(Glycine)

Number of papers citing our products

Chemical structure

IOX2(Glycine)

3D structure

Chemical Properties of IOX2(Glycine)

Cas No. 931398-72-0 SDF Download SDF
PubChem ID 54685215 Appearance Powder
Formula C19H16N2O5 M.Wt 352.34
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 25 mg/mL (70.95 mM; Need ultrasonic)
Chemical Name 2-[(1-benzyl-4-hydroxy-2-oxoquinoline-3-carbonyl)amino]acetic acid
SMILES C1=CC=C(C=C1)CN2C3=CC=CC=C3C(=C(C2=O)C(=O)NCC(=O)O)O
Standard InChIKey CAOSCCRYLYQBES-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H16N2O5/c22-15(23)10-20-18(25)16-17(24)13-8-4-5-9-14(13)21(19(16)26)11-12-6-2-1-3-7-12/h1-9,24H,10-11H2,(H,20,25)(H,22,23)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of IOX2(Glycine)

DescriptionPotent inhibitor of HIF-1α prolyl hydroxylase-2 (PHD2) (IC50 = 21 nM). Displays over 100-fold selectivity for PHD2 over factor inhibiting HIF-1 (FIH-1) and histone demethylases JMJD2A, JMJD2C, JMJD2E and JMJD3. Cell permeable.

IOX2(Glycine) Dilution Calculator

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IOX2(Glycine) Molarity Calculator

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Preparing Stock Solutions of IOX2(Glycine)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8382 mL 14.1908 mL 28.3817 mL 56.7634 mL 70.9542 mL
5 mM 0.5676 mL 2.8382 mL 5.6763 mL 11.3527 mL 14.1908 mL
10 mM 0.2838 mL 1.4191 mL 2.8382 mL 5.6763 mL 7.0954 mL
50 mM 0.0568 mL 0.2838 mL 0.5676 mL 1.1353 mL 1.4191 mL
100 mM 0.0284 mL 0.1419 mL 0.2838 mL 0.5676 mL 0.7095 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on IOX2(Glycine)

IOX2 is a novel and potent inhibitor of HIF-1α prolyl hydroxylase-2 (PHD2) with IC50 of 21 nM in a cell-free assay, >100-fold selectivity over JMJD2A, JMJD2C, JMJD2E, JMJD3, or the 2OG oxygenase FIH. [1, 2]

The hypoxia inducible factor (HIF) system is related to the signaling of low oxygen (hypoxia) in animals. The levels of HIF-α isoforms are controlled by an oxygen-dependent manner by the activity of the HIF prolyl-hydroxylases (PHD or EGLN enzymes), which are Fe(II) and 2-oxoglutarate (2OG) dependent oxygenases. IOX2 inhibits HIF-1α hydroxylation in RCC4 cells at 50 μM. [1, 2]

References:
Murray JK1, Balan C, Allgeier AM et al.  Dipeptidyl-quinolone derivatives inhibit hypoxia inducible factor-1α prolyl hydroxylases-1, -2, and -3 with altered selectivity. J Comb Chem. 2010 Sep 13;12(5):676-86. doi: 10.1021/cc100073a.
Chowdhury R1, Candela-Lena JI, Chan MC et al.  Selective small molecule probes for the hypoxia inducible factor (HIF) prolyl hydroxylases. ACS Chem Biol. 2013 Jul 19;8(7):1488-96. doi: 10.1021/cb400088q. Epub 2013 Jun 12.

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References on IOX2(Glycine)

Dipeptidyl-quinolone derivatives inhibit hypoxia inducible factor-1alpha prolyl hydroxylases-1, -2, and -3 with altered selectivity.[Pubmed:20666436]

J Comb Chem. 2010 Sep 13;12(5):676-86.

Intracellular levels of the hypoxia-inducible transcription factor (HIF) are regulated under normoxic conditions by prolyl hydroxylases (PHD1, 2, and 3). Treatment of cells with PHD inhibitors stabilizes HIF-1alpha, eliciting an artificial hypoxic response that includes the transcription of genes involved in erythropoiesis, angiogenesis, and glycolysis. The different in vivo roles of the three PHD isoforms are not yet known, making a PHD-selective inhibitor useful as a biological tool. Although several chemical series of PHD inhibitors have been described, significant isoform selectivity has not been reported. Here we report the synthesis and activity of dipeptidyl analogues derived from a potent but non-selective quinolone scaffold. The compounds were prepared by Pd-catalyzed reductive carbonylation of the 6-iodoquinolone derivative to form the aldehyde directly, which was then attached to a solid support via reductive amination. Amino acids were coupled, and the resulting dipeptidyl-quinolone derivatives were screened, revealing retention of PHD inhibitory activity but an altered PHD1, 2, and 3 selectivity profile. The compounds were found to be approximately 10-fold more potent against PHD1 and PHD3 than against PHD2, whereas the specific parent compound had shown no appreciable selectivity among the different PHD isoforms.

Description

IOX2 is a specific prolyl hydroxylase-2 (PHD2) inhibitor with IC50 of 22 nM.

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