Atpenin A5 A mitochondrial complex II inhibitor able to protect against cardiac-reperfusion

Atpenin A5 (CAS 119509-24-9)

Atpenin A5 | CAS 119509-24-9 is rated 5.0 out of 5 by 1.
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Synonym: 3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
Application: A mitochondrial complex II inhibitor able to protect against cardiac-reperfusion
CAS Number: 119509-24-9
Purity: ≥95%
Molecular Weight: 366.2
Molecular Formula: C15H21Cl2NO5
* Refer to Certificate of Analysis for lot specific data (including water content).
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Atpenin A5 belongs to a class of antifungal antibiotics isolated from Penicillium sp. The atpenins are effective against filamentous fungi, particularly Trichophyton sp., and are specific and potent inhibitors of the succinate-ubiquinone reducatase activity of the mitochondrial complex II. Atpenin A5 is the most effective inhibitor against complex II from all the atpenins and has been shown to protect against cardiac-reperfusion injury in rat studies through the stimulation of mitochondrial KATP channels. Atpenin A5 is an inhibitor of SDHB, SDHC and SDHD.


References

1. Omura, S., et al. 1988. J. Antibiot. 41: 1769-1773. PMID: 3209470
2. Kumagai, H., et al. 1990. J. Antibiot. 43: 1553-1558. PMID: 2276974
3. Miyadera, H., et al. 2003. Proc. Natl. Acad. Sci. U.S.A. 100: 473-477. PMID: 12515859
4. Wojtovich, A.P., et al. 2009. Basic Res. Cardiol. 104: 121-129. PMID: 19242645
5. Ohtawa, M., et al. 2009. J. Antibiot. 62: 289-294. PMID: 19373276

Appearance :
Powder
Physical State :
Solid
Derived From :
Synthetic, originally isolated from Penicillium sp strain FO-125
Solubility :
Soluble in acetone, acetonitrile, chloroform, ethyl acetate, DMSO, methanol, and 100% ethanol. Insoluble in water, and hexane.
Storage :
Store at -20° C
Melting Point :
83-86° C
Boiling Point :
532.59° C at 760 mmHg (Predicted)
Density :
1.31 g/cm3
Refractive Index :
n20D 1.53 (Predicted)
IC50 :
bovine heart complex II: IC50 = 3.6 nM; fumarate reductase: IC50 = 12 nM (Ascaris suum); E. coli succinate dehydrogenase: IC50 = 5 µM
pK Values :
pKa: 4.5, pKb: 0.98
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
CJ8800000
PubChem CID :
197273
SMILES :
C[C@@H](C[C@H](C)C(=O)C1=C(NC(=C(C1=O)OC)OC)O)[C@H](CCl)Cl

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Certificate of Analysis

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Atpenin A5  Product Citations

See how others have used Atpenin A5. Click on the entry to view the PubMed entry .

Citations 1 to 9 of 9 total

PMID: # 26660760  Hancock, CN. et al. 2016. Amino Acids. 48: 859-72.

PMID: # 27011353  Sanman, LE. et al. 2016. Elife. 5:

PMID: # 24515115  Quinlan, CL. et al. 2014. J. Biol. Chem. 289: 8312-25.

PMID: # 24703695  Mishra, P. et al. 2014. Cell metabolism. 19: 630-41.

PMID: # 24587137  Orr, AL. et al. 2014. PloS one. 9: e89938.

PMID: # 24746616  Hey-Mogensen, M. et al. 2014. Free Radic. Biol. Med. 72: 149-55.

PMID: # 23583329  Perevoshchikova, IV. et al. 2013. Free Radic. Biol. Med. 61: 298-309.

PMID: # 23886887  Jones, AJ. et al. 2013. Anal. Biochem. 442: 19-23.

PMID: # 12515859  Miyadera, H. et al. 2003. Proc. Natl. Acad. Sci. U.S.A. 100: 473-477.

Citations 1 to 9 of 9 total

What is the desired solvent for this product?

Asked by: hawkeye11
Thank you for your question. All of the information I can find leads me to believe that sc-202475 is not water soluble, but it is soluble in acetone, acetonitrile, chloroform, ethyl acetate, DMSO, methanol or ethanol. If you have any further questions or concerns, please contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-11
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Rated 5 out of 5 by from Bonke Bonke, E. et al. (PubMed 26116786) investigated how divalent manganese ions could stimulate mitochondrial ROS production. In succinate fueled bovine heart submitochindrial particles, the manganese ion induced hydrogen peroxide production was blocked by the specific complex II ubiquinone binding site (IIQ) inhibitor Atpenin A5. This suggests that site IIQ was the source of the ROS. -SCBT Publication Review
Date published: 2015-04-05
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