ChemicalBook > CAS DataBase List > Adaptaquin

Adaptaquin

Product Name: Adaptaquin
CAS No.: 385786-48-1
Chemical Name: Adaptaquin
Synonyms: Adaptaquin;Adaptaquin, 10 mM in DMSO;HIF Prolyl Hydroxylase Inhibitor - CAS 385786-48-1 - Calbiochem;7-[(4-Chlorophenyl)[(3-hydroxy-2-pyridinyl)amino]methyl]-8-quinolinol;7-((4-Chlorophenyl)((3-hydroxypyridin-2-yl)amino)methyl)quinolin-8-ol;8-Quinolinol, 7-[(4-chlorophenyl)[(3-hydroxy-2-pyridinyl)amino]methyl]-;Hypoxia-inducible factors,peroxidation,mitochondrial,HIFs,HIF-PH,inhibit,HIF-PHD2,HIF/HIF Prolyl-Hydroxylase,Adaptaquin,Inhibitor
CBNumber: CB74665884
Molecular Formula: C21H16ClN3O2
Formula Weight: 377.82
MOL File: 385786-48-1.mol

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Adaptaquin Property

Boiling point:: 650.9±55.0 °C(Predicted)
Density: 1.437±0.06 g/cm3(Predicted)
storage temp.: -20C
solubility: ≤30mg/ml in DMSO;30mg/ml in dimethyl formamide
form: Tan solid
pka: 4.07±0.50(Predicted)
color: White to yellow

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 400084
Product name: HIF Prolyl Hydroxylase Inhibitor - CAS 385786-48-1 - Calbiochem
Packaging: 10mg
Price: $139
Updated: 2025/07/31

Cayman Chemical

Product number: 19720
Product name: Adaptaquin
Purity: ≥95%
Packaging: 5mg
Price: $73
Updated: 2024/03/01

Cayman Chemical

Product number: 19720
Product name: Adaptaquin
Purity: ≥95%
Packaging: 10mg
Price: $138
Updated: 2024/03/01

Cayman Chemical

Product number: 19720
Product name: Adaptaquin
Purity: ≥95%
Packaging: 50mg
Price: $575
Updated: 2024/03/01

Tocris

Product number: 5953
Product name: Adaptaquin
Purity: ≥97%(HPLC)
Packaging: 50
Price: $682
Updated: 2021/12/16

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Adaptaquin Chemical Properties,Usage,Production

Uses

General Uses:Ischemic injury Research, Renal anemia, HIF Prolyl Hydroxylase Inhibitor, Antioxidant, NeuroprotectiveDescription:Adaptaquin inhibits the HIF PHDs in brain in a dose dependent fashion and penetrates blood brain barrier (BBB). Exhibited functional recovery in intra-cerebral hemorrhage rat model; inhibits ATF4 gene. Potent HIF PHD inhibitor (hypoxia inducible factor), Selective PDH2 inhibitor.This compound is suitable for pyruvate dehydrogenase (PDH) related research.

Biological Activity

adaptaquin is a selective hydroxyquinoline hif prolyl hydroxylase (hif-phd) inhibitor [1][2].the hypoxia-inducible factor prolyl hydroxylase domain enzymes (hif-phds) are a family of oxygen sensors that has been implicated in neuronal survival. catalysis by the hif-phds destabilizes the transcriptional activator hif-1a under normoxia. hif-phds are promising target candidates for mitochondrial protection in paradigms of oxidative stress. the inhibition of hif-phds prevented neuronal cell death induced by mitochondrial toxins [1][2].adaptaquin is a hydroxyquinoline hif-phd inhibitor. adaptaquin inhibited purified and recombinant phd2. adaptaquin (30 mg/kg) penetrated the blood-brain barrier, resulting in inhibition of the oxygen-sensing hif-phds and activation of hif-dependent gene expression [1]. in ht-22 cells, adaptaquin protected against glutamate-induced cell death. adaptaquin could also restore the mitochondrial atp production [2].in intracerebral hemorrhage (ich) mice model, adaptaquin decreased edema and significantly improved tape removal task, which were associated with a reduction in the number of degenerating neurons in perihematomal and hematomal areas of the mouse striatum [1].

Enzyme inhibitor

This brain-penetrant PHD2 inhibitor and antioxidant (FW = 377.82 g/mol; CAS 385786-48-1; Soluble to 100 mM in DMSO), also named 7-[(4chlorophenyl)[(3-hydroxy-2-pyridinyl)amino]methyl]-8-quinolinol, targets Hypoxia-Inducible Factor (or HIF) prolyl hydroxylase-2, a critical regulator of hematopoietic stem cell (HSC) maintenance during steadystate and stress. Indeed, this branched oxyquinoline molecule was named adaptaquin (AQ) to signify its ability to inhibit the HIF-PHDs and activate adaptive responses to hypoxia. Hypoxia is a prominent feature in the maintenance of HSC quiescence and multipotency. Adaptaquin also exhibits neuroprotective effects, enhancing functional recovery in rodent intracerebral hemorrhage models, via inhibition of ATF4 dependent genes.

in vivo

Adaptaquin (30 mg/kg; intraperitoneal injection; 7 days) has a protective effect in a mouse model of Parkinson's disease^[2].

Animal Model:	Adult male C57BL/6 mice (10-12 weeks) treated 6-OHDA hydrobromide (HY-B1081A)^[2]
Dosage:	30 mg/kg
Administration:	Intraperitoneal injection; 7 days
Result:	Enhanced survival of dopaminergic neurons and substantially protected their striatal projections. Significantly enhanced retention of nigrostriatal function.

storage

Store at -20°C

References

[1]. karuppagounder ss, alim i, khim sj, et al. therapeutic targeting of oxygen-sensing prolyl hydroxylases abrogates atf4-dependent neuronal death and improves outcomes after brain hemorrhage in several rodent models. sci transl med. 2016 mar 2;8(328):328ra29.
[2]. neitemeier s, dolga am, honrath b, et al. inhibition of hif-prolyl-4-hydroxylases prevents mitochondrial impairment and cell death in a model of neuronal oxytosis. cell death dis. 2016 may 5;7:e2214.

Adaptaquin Preparation Products And Raw materials

Raw materials

Preparation Products

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Adaptaquin Suppliers

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385786-48-1, AdaptaquinRelated Search:

Adaptaquin

HIF Prolyl Hydroxylase Inhibitor - CAS 385786-48-1 - Calbiochem

7-[(4-Chlorophenyl)[(3-hydroxy-2-pyridinyl)amino]methyl]-8-quinolinol

Hypoxia-inducible factors,peroxidation,mitochondrial,HIFs,HIF-PH,inhibit,HIF-PHD2,HIF/HIF Prolyl-Hydroxylase,Adaptaquin,Inhibitor

8-Quinolinol, 7-[(4-chlorophenyl)[(3-hydroxy-2-pyridinyl)amino]methyl]-

7-((4-Chlorophenyl)((3-hydroxypyridin-2-yl)amino)methyl)quinolin-8-ol

Adaptaquin, 10 mM in DMSO

385786-48-1