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SML0652

Sigma-Aldrich

IOX2

≥98% (HPLC)

Synonym(s):

JICL38, N-[[1,2-Dihydro-4-hydroxy-2-oxo-1-(phenylmethyl)-3-quinolinyl]carbonyl]-glycine, N-[[4-Hydroxy-2-oxo-1-(phenylmethyl)-1,2-dihydro-3-quinolinyl]carbonyl]glycine

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About This Item

Empirical Formula (Hill Notation):
C19H16N2O5
CAS Number:
931398-72-0
Molecular Weight:
352.34
MDL number:
MFCD22580424
UNSPSC Code:
12352200
PubChem Substance ID:
329825575
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

OC(C1=C(N2CC3=CC=CC=C3)C=CC=C1)=C(C(NCC(O)=O)=O)C2=O

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)

InChI key

CAOSCCRYLYQBES-UHFFFAOYSA-N

Related Categories

Application

IOX2 has been used as PHD inhibitor to induce pseudo-hypoxia.

Biochem/physiol Actions

IOX2 is selective and potent inhibitor of prolyl hydroxylases (PHD). Stabilization of HIF-1R through inhibition of PHD has been examined as a potential treatment for ischemic diseases including anemia, myocardial infarction, and stroke. IOX2 is a selective inhibitor of the hypoxia inducible factor (HIF) prolyl-hydroxylases (PHD) that exhibits up-regulation of HIF1a in zebrafish. For full characterization details, please visit the IOX2 probe summary on the Structural Genomics Consortium (SGC) website.

To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc

Features and Benefits

IOX2 is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit sigma.com/SGC.
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Resveratrol integrates metabolic and growth effects in PC3 prostate cancer cells-involvement of prolyl hydroxylase and hypoxia inducible factor-1
Fonseca J, et al.
Oncology Letters (2018)
Pieter-Jan Stiers et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 34(2), 333-348 (2018-11-20)
Tissue engineering holds great promise for bone regenerative medicine, but clinical translation remains challenging. An important factor is the low cell survival after implantation, primarily caused by the lack of functional vasculature at the bone defect. Interestingly, bone development and
Hu Peng et al.
American journal of physiology. Renal physiology, 318(2), F468-F474 (2019-12-17)
Acute pyelonephritis is frequently associated with metabolic acidosis. We previously reported that metabolic acidosis stimulates expression of hypoxia-inducible factor (HIF)-1α-induced target genes such as stromal derived factor-1 and cathelicidin, an antimicrobial peptide. Since the collecting duct (CD) plays a pivotal
Yuetao Zhao et al.
Biochemical and biophysical research communications, 517(2), 201-209 (2019-07-25)
Lung cancer is the most commonly diagnosed cancer and accounts for most cancer-related mortalities worldwide. The high expression of programmed death ligand 1 (PD-L1) is an important factor that promotes immune escape of lung cancer, thus aggravates chemotherapy resistance and
Dirk Friedrich et al.
Infection and immunity, 87(7) (2019-05-01)
The fungal pathogen Histoplasma capsulatum causes a spectrum of disease, ranging from local pulmonary infection to disseminated disease. The organism seeks residence in macrophages, which are permissive for its survival. Hypoxia-inducible factor 1α (HIF-1α), a principal regulator of innate immunity
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