Atpenin A5 | CAS# 119509-24-9 | Mitochondrial Complex II Enzyme Inhibitor

MedKoo Cat#: 573317 | Name: Atpenin A5

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Atpenin A5, an antifungal antibiotic, is an ubiquinone-binding site inhibitor of succinate dehydrogenase. Atpenin A5 has cardioprotective effects against simulated ischemia-reperfusion injury in cardiomyocytes.

Chemical Structure

Atpenin A5

CAS#119509-24-9

Theoretical Analysis

MedKoo Cat#: 573317

Name: Atpenin A5

CAS#: 119509-24-9

Chemical Formula: C15H21Cl2NO5

Exact Mass: 365.0797

Molecular Weight: 366.24

Elemental Analysis: C, 49.19; H, 5.78; Cl, 19.36; N, 3.82; O, 21.84

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 650.00	2 Weeks

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Related CAS #

119509-24-9

Synonym

Atpenin A5

IUPAC/Chemical Name

3-((2S,4S,5R)-5,6-dichloro-2,4-dimethylhexanoyl)-4-hydroxy-5,6-dimethoxypyridin-2(1H)-one

InChi Key

OVULNOOPECCZRG-CIUDSAMLSA-N

InChi Code

1S/C15H21Cl2NO5/c1-7(9(17)6-16)5-8(2)11(19)10-12(20)13(22-3)15(23-4)18-14(10)21/h7-9H,5-6H2,1-4H3,(H2,18,20,21)/t7-,8-,9-/m0/s1

SMILES Code

c1(c(c(c(c([nH]1)OC)OC)O)C([C@H](C[C@@H]([C@H](CCl)Cl)C)C)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 366.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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Mitochondrial complex II regulates a distinct oxygen sensing mechanism in monocytes. Hum Mol Genet. 2017 Apr 1;26(7):1328-1339. doi: 10.1093/hmg/ddx041. PMID: 28204537; PMCID: PMC6074833. 5: Selby TP, Hughes KA, Rauh JJ, Hanna WS. Synthetic atpenin analogs: Potent mitochondrial inhibitors of mammalian and fungal succinate-ubiquinone oxidoreductase. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1665-8. doi: 10.1016/j.bmcl.2010.01.066. Epub 2010 Jan 21. PMID: 20137945. 6: Wojtovich AP, Brookes PS. The complex II inhibitor atpenin A5 protects against cardiac ischemia-reperfusion injury via activation of mitochondrial KATP channels. Basic Res Cardiol. 2009 Mar;104(2):121-9. doi: 10.1007/s00395-009-0001-y. Epub 2009 Feb 26. PMID: 19242645; PMCID: PMC2776710. 7: Siebels I, Dröse S. Q-site inhibitor induced ROS production of mitochondrial complex II is attenuated by TCA cycle dicarboxylates. Biochim Biophys Acta. 2013 Oct;1827(10):1156-64. doi: 10.1016/j.bbabio.2013.06.005. Epub 2013 Jun 22. 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Manganese ions induce H2O2 generation at the ubiquinone binding site of mitochondrial complex II. Arch Biochem Biophys. 2015 Aug 15;580:75-83. doi: 10.1016/j.abb.2015.06.011. Epub 2015 Jun 24. PMID: 26116786. 12: Mailloux RJ, Young A, Chalker J, Gardiner D, O'Brien M, Slade L, Brosnan JT. Choline and dimethylglycine produce superoxide/hydrogen peroxide from the electron transport chain in liver mitochondria. FEBS Lett. 2016 Dec;590(23):4318-4328. doi: 10.1002/1873-3468.12461. Epub 2016 Nov 9. PMID: 27761911. 13: Sarkadi B, Meszaros K, Krencz I, Canu L, Krokker L, Zakarias S, Barna G, Sebestyen A, Papay J, Hujber Z, Butz H, Darvasi O, Igaz P, Doczi J, Luconi M, Chinopoulos C, Patocs A. Glutaminases as a Novel Target for SDHB-Associated Pheochromocytomas/Paragangliomas. Cancers (Basel). 2020 Mar 5;12(3):599. doi: 10.3390/cancers12030599. PMID: 32150977; PMCID: PMC7139890. 14: Dröse S, Bleier L, Brandt U. A common mechanism links differently acting complex II inhibitors to cardioprotection: modulation of mitochondrial reactive oxygen species production. Mol Pharmacol. 2011 May;79(5):814-22. doi: 10.1124/mol.110.070342. Epub 2011 Jan 28. PMID: 21278232. 15: Fuhrmann DC, Wittig I, Brüne B. TMEM126B deficiency reduces mitochondrial SDH oxidation by LPS, attenuating HIF-1α stabilization and IL-1β expression. Redox Biol. 2019 Jan;20:204-216. doi: 10.1016/j.redox.2018.10.007. Epub 2018 Oct 19. PMID: 30368040; PMCID: PMC6202876. 16: Huang LS, Lümmen P, Berry EA. Crystallographic investigation of the ubiquinone binding site of respiratory Complex II and its inhibitors. Biochim Biophys Acta Proteins Proteom. 2021 Sep;1869(9):140679. doi: 10.1016/j.bbapap.2021.140679. Epub 2021 Jun 3. PMID: 34089891; PMCID: PMC8516616. 17: Kumagai H, Nishida H, Imamura N, Tomoda H, Omura S, Bordner J. The structures of atpenins A4, A5 and B, new antifungal antibiotics produced by Penicillium sp. J Antibiot (Tokyo). 1990 Dec;43(12):1553-8. doi: 10.7164/antibiotics.43.1553. PMID: 2276974. 18: Quinlan CL, Orr AL, Perevoshchikova IV, Treberg JR, Ackrell BA, Brand MD. Mitochondrial complex II can generate reactive oxygen species at high rates in both the forward and reverse reactions. J Biol Chem. 2012 Aug 3;287(32):27255-64. doi: 10.1074/jbc.M112.374629. Epub 2012 Jun 11. PMID: 22689576; PMCID: PMC3411067. 19: Goncalves RL, Rothschild DE, Quinlan CL, Scott GK, Benz CC, Brand MD. Sources of superoxide/H2O2 during mitochondrial proline oxidation. Redox Biol. 2014 Jul 18;2:901-9. doi: 10.1016/j.redox.2014.07.003. PMID: 25184115; PMCID: PMC4143814. 20: Markevich NI, Markevich LN, Hoek JB. Computational Modeling Analysis of Generation of Reactive Oxygen Species by Mitochondrial Assembled and Disintegrated Complex II. Front Physiol. 2020 Oct 16;11:557721. doi: 10.3389/fphys.2020.557721. PMID: 33178032; PMCID: PMC7596731.