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SML2175

Sigma-Aldrich

GSK360A

≥98% (HPLC)

Synonyme(s) :

GSK 1120360A, GSK1120360A, N-[[1-(2-Cyclopropylethyl)-6-fluoro-1,2-dihydro-4-hydroxy-2-oxo-3-quinolinyl]carbonyl]glycine, N-[[1-(2-Cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydro-3-quinolinyl]carbonyl]glycine

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About This Item

Formule empirique (notation de Hill):
C17H17FN2O5
Numéro CAS:
931399-19-8
Poids moléculaire :
348.33
Numéro MDL:
MFCD27977959
Code UNSPSC :
12352200

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear (warmed)

Température de stockage

2-8°C

Chaîne SMILES 

OC(C1=C(N2CCC3CC3)C=CC(F)=C1)=C(C(NCC(O)=O)=O)C2=O

InChI

1S/C17H17FN2O5/c18-10-3-4-12-11(7-10)15(23)14(16(24)19-8-13(21)22)17(25)20(12)6-5-9-1-2-9/h3-4,7,9,23H,1-2,5-6,8H2,(H,19,24)(H,21,22)

Clé InChI

TYHRZQVUPPODPT-UHFFFAOYSA-N

Actions biochimiques/physiologiques

GSK360A (GSK1120360A) is an orally active HIF-prolyl 4-hydroxylase (HIF-PHD) inhibitor that targets all three HIF-PHD isoforms (PHD1 > PHD2 = PHD3) with high potency (IC50 from 10-120 nM) in a 2-oxoglutarate (2-OG)-competitive manner. GSK360A promotes cardiomyocyte mitochondrial aerobic glycolysis under normoxic conditions by stabilizing cellular hypoxia-inducible factor-1 (HIF-1) and thereby upregulating HIF-1α target genes transcription (50 μM for 8 hrs in murine cardiomyocyte HL-1 cultures), including pyruvate dehydrogenase kinase-1 (PDK1) and hexokinase II (HKII). GSK360A treatment is shown to protect against acute myocardial ischemia–reperfusion injury (IRI) both in cultures and in rats in vivo (30 mg/kg p.o.) by reducing mitochondrial permeability transition pore (MPTP) opening and oxidative stress during IRI.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Weike Bao et al.
Journal of cardiovascular pharmacology, 56(2), 147-155 (2010-08-18)
Hypoxia inducible factors (HIFs) are transcription factors that are regulated by HIF-prolyl 4-hydroxylases (PHDs) in response to changes in oxygen tension. Once activated, HIFs play an important role in angiogenesis, erythropoiesis, proliferation, cell survival, inflammation, and energy metabolism. We hypothesized
Sang-Ging Ong et al.
Cardiovascular research, 104(1), 24-36 (2014-07-30)
Hypoxia-inducible factor-1 (HIF-1) has been reported to promote tolerance against acute myocardial ischaemia-reperfusion injury (IRI). However, the mechanism through which HIF-1 stabilization actually confers this cardioprotection is not clear. We investigated whether HIF-1α stabilization protects the heart against acute IRI
J P Gumucio et al.
Bone & joint research, 6(1), 57-65 (2017-01-22)
Rotator cuff tears are among the most frequent upper extremity injuries. Current treatment strategies do not address the poor quality of the muscle and tendon following chronic rotator cuff tears. Hypoxia-inducible factor-1 alpha (HIF-1α) is a transcription factor that activates
Jin Zhou et al.
PloS one, 12(9), e0184049-e0184049 (2017-09-08)
There is interest in pharmacologic preconditioning for end-organ protection by targeting the HIF system. This can be accomplished by inhibition of prolyl 4-hydroxylase (PHD). GSK360A is an orally active PHD inhibitor that has been previously shown to protect the failing
Tomohiro Suhara et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(37), 11642-11647 (2015-09-02)
Loss of prolyl hydroxylase 2 (PHD2) activates the hypoxia-inducible factor-dependent hypoxic response, including anaerobic glycolysis, which causes large amounts of lactate to be released from cells into the circulation. We found that Phd2-null mouse embryonic fibroblasts (MEFs) produced more lactate

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