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Adaptaquin

Catalog No: 20552
CAS Number: 385786-48-1
Purity: 98% Min.

Adaptaquin is a hydroxyquinoline inhibitor of HIF-PHD enzymes. Adaptaquin reduces neuronal death and behavioral deficits after intracerebral hemorrhage (ICH) in several rodent models without affecting total iron or zinc distribution in the brain.

For research use only. We do not sell to patients.

Chemical Information

NameAdaptaquin
Iupac Chemical Name7-[(4-Chlorophenyl)[(3-hydroxy-2-pyridinyl)amino]methyl]-8-quinolinol
SynonymsAdaptaquin
Molecular FormulaC21H16ClN3O2
Molecular Weight377.82
SmileOC1=C2N=CC=CC2=CC=C1C(C3=CC=C(Cl)C=C3)NC4=NC=CC=C4O
InChiKeyKKYHNYRUBSYTCZ-UHFFFAOYSA-N
InChiInChI=1S/C21H16ClN3O2/c22-15-8-5-14(6-9-15)18(25-21-17(26)4-2-12-24-21)16-10-7-13-3-1-11-23-19(13)20(16)27/h1-12,18,26-27H,(H,24,25)
CAS Number385786-48-1
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Ordering Information

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FormulationSolid powder
Purity98% Min.
StorageDry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
SolubilitySoluble in DMSO
Handling
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
HS Code
Coming soon.
Targets
Mechanism
Cell study
Animal study
Clinical study

1: Ratan RR. The Chemical Biology of Ferroptosis in the Central Nervous System. Cell Chem Biol. 2020 May 21;27(5):479-498. doi: 10.1016/j.chembiol.2020.03.007. Epub 2020 Apr 2. PMID: 32243811; PMCID: PMC7245561.


2: Aimé P, Karuppagounder SS, Rao A, Chen Y, Burke RE, Ratan RR, Greene LA. The drug adaptaquin blocks ATF4/CHOP-dependent pro-death Trib3 induction and protects in cellular and mouse models of Parkinson's disease. Neurobiol Dis. 2020 Mar;136:104725. doi: 10.1016/j.nbd.2019.104725. Epub 2020 Jan 3. PMID: 31911115; PMCID: PMC7545957.


3: Li K, Li T, Wang Y, Xu Y, Zhang S, Culmsee C, Wang X, Zhu C. Sex differences in neonatal mouse brain injury after hypoxia-ischemia and adaptaquin treatment. J Neurochem. 2019 Sep;150(6):759-775. doi: 10.1111/jnc.14790. Epub 2019 Jul 28. PMID: 31188470.


4: Vetrovoy O, Rybnikova E. Neuroprotective action of PHD inhibitors is predominantly HIF-1-independent: An Editorial for 'Sex differences in neonatal mouse brain injury after hypoxia-ischemia and adaptaquin treatment' on page 759. J Neurochem. 2019 Sep;150(6):645-647. doi: 10.1111/jnc.14822. Epub 2019 Aug 2. PMID: 31373011.


5: Poloznikov AA, Nikulin SV, Zakhariants AA, Khristichenko AY, Hushpulian DM, Gazizov IN, Tishkov VI, Gazaryan IG. "Branched Tail" Oxyquinoline Inhibitors of HIF Prolyl Hydroxylase: Early Evaluation of Toxicity and Metabolism Using Liver- on-a-chip. Drug Metab Lett. 2019;13(1):45-52. doi: 10.2174/1872312813666181129100950. PMID: 30488807.


6: David BT, Curtin JJ, Brown JL, Coutts DJC, Boles NC, Hill CE. Treatment with hypoxia-mimetics protects cultured rat Schwann cells against oxidative stress- induced cell death. Glia. 2021 Sep;69(9):2215-2234. doi: 10.1002/glia.24019. Epub 2021 May 21. PMID: 34019306.


7: Karuppagounder SS, Alim I, Khim SJ, Bourassa MW, Sleiman SF, John R, Thinnes CC, Yeh TL, Demetriades M, Neitemeier S, Cruz D, Gazaryan I, Killilea DW, Morgenstern L, Xi G, Keep RF, Schallert T, Tappero RV, Zhong J, Cho S, Maxfield FR, Holman TR, Culmsee C, Fong GH, Su Y, Ming GL, Song H, Cave JW, Schofield CJ, Colbourne F, Coppola G, Ratan RR. 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. doi: 10.1126/scitranslmed.aac6008. PMID: 26936506; PMCID: PMC5341138.


8: Neitemeier S, Dolga AM, Honrath B, Karuppagounder SS, Alim I, Ratan RR, Culmsee C. 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(5):e2214. doi: 10.1038/cddis.2016.107. PMID: 27148687; PMCID: PMC4917646.


9: Poloznikov AA, Nersisyan SA, Hushpulian DM, Kazakov EH, Tonevitsky AG, Kazakov SV, Vechorko VI, Nikulin SV, Makarova JA, Gazaryan IG. HIF Prolyl Hydroxylase Inhibitors for COVID-19 Treatment: Pros and Cons. Front Pharmacol. 2021 Jan 29;11:621054. doi: 10.3389/fphar.2020.621054. PMID: 33584306; PMCID: PMC7878396.


10: David BT, Curtin JJ, Brown JL, Scorpio K, Kandaswamy V, Coutts DJC, Vivinetto A, Bianchimano P, Karuppagounder SS, Metcalfe M, Cave JW, Hill CE. Temporary induction of hypoxic adaptations by preconditioning fails to enhance Schwann cell transplant survival after spinal cord injury. Glia. 2023 Mar;71(3):648-666. doi: 10.1002/glia.24302. Epub 2022 Dec 24. PMID: 36565279.


11: Wei GZ, Saraswat Ohri S, Khattar NK, Listerman AW, Doyle CH, Andres KR, Karuppagounder SS, Ratan RR, Whittemore SR, Hetman M. Hypoxia-inducible factor prolyl hydroxylase domain (PHD) inhibition after contusive spinal cord injury does not improve locomotor recovery. PLoS One. 2021 Apr 5;16(4):e0249591. doi: 10.1371/journal.pone.0249591. PMID: 33819286; PMCID: PMC8021188.


12: Poloznikov AA, Nikulin SV, Hushpulian DM, Khristichenko AY, Osipyants AI, Asachenko AF, Shurupova OV, Savin SS, Lee SH, Gaisina IN, Thatcher GRJ, Narciso A, Chang EP, Kazakov SV, Krucher N, Tishkov VI, Thomas B, Gazaryan IG. Structure-Activity Relationships and Transcriptomic Analysis of Hypoxia- Inducible Factor Prolyl Hydroxylase Inhibitors. Antioxidants (Basel). 2022 Jan 24;11(2):220. doi: 10.3390/antiox11020220. PMID: 35204103; PMCID: PMC8868400.


13: Osipyants AI, Poloznikov AA, Smirnova NA, Hushpulian DM, Khristichenko AY, Chubar TA, Zakhariants AA, Ahuja M, Gaisina IN, Thomas B, Brown AM, Gazaryan IG, Tishkov VI. L-ascorbic acid: A true substrate for HIF prolyl hydroxylase? Biochimie. 2018 Apr;147:46-54. doi: 10.1016/j.biochi.2017.12.011. Epub 2017 Dec 28. PMID: 29289682; PMCID: PMC6460286.

Chemical Structure

20552 - Adaptaquin | CAS 385786-48-1

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