Piericidin A CAS: 2738-64-9
MF: C25H37NO4
MW: 415.57
An antibiotic and a member of the Class I inhibitors that acts as an effective inhibitor of Complex I.

Piericidin A (CAS 2738-64-9)

Piericidin A | CAS 2738-64-9 is rated 5.0 out of 5 by 1.
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Synonym: Piericidin A1; Shaoguanmycin B; Antibiotic MT 1882-I
Application: An antibiotic and a member of the Class I inhibitors that acts as an effective inhibitor of Complex I
CAS Number: 2738-64-9
Purity: ≥95%
Molecular Weight: 415.57
Molecular Formula: C25H37NO4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
Submit a review for this product and receive 15 CruzCredits

Piericidin A is an antibiotic and a member of the Class I inhibitors. The antibiotic acts as an effective inhibitor of the bacterial and mitochondrial type I NDUFS (NADH-ubiquinone oxidoreductases, Complex I). Class I inhibitors such as annonin IV, phenalamid A2, and Piericidin A, among others, are competitive inhibitors of H6PD (glucose dehydrogenase) and partially competitive inhibitors of Complex I. Research indicates that Piericidin A prevents the translocation of the NADH-induced proton in the NADH-endogenous ubiquinone reductase reaction, and that the inhibitor binds near the NUOD-NUOB interface of Complex I.


References

1. Ramsay, R.R., et al. 1991. Biochem. J. 273: 481-484. PMID: 1991043
2. Friedrich, T., et al. 1994. Eur. J. Biochem. 219: 691-698. PMID: 8307034
3. Darrouzet, E., et al. 1998. FEBS Lett. 43: 34-38. PMID: 9684860
4. Galkin, A.S., et al. 1999. FEBS Lett. 451: 157-161. PMID: 10371157
5. Prieur, I., et al. 2001. Biochim. Biophys. Acta. 1504: 173-178. PMID: 11245783

Appearance :
Oil
Physical State :
Liquid
Derived From :
Streptomyces sp.
Solubility :
Soluble in 100% ethanol, DMF, DMSO, and water (poorly).
Storage :
Store at -20° C
Melting Point :
220.48° C (Predicted) (tautomer)
Boiling Point :
~591.7° C at 760 mmHg (Predicted) (tautomer)
Density :
~1.1 g/mL (Predicted) (tautomer)
Refractive Index :
n20D 1.53 (Predicted)
IC50 :
L929: IC50 = 0.43 nM (mouse); Mitochondrial complex I; NADH oxidoreductase: IC50 = 5 nM (bovine)
pK Values :
pKa: 5.22 (Predicted), pKb: 10.17 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
1
RTECS :
YD4588000
PubChem CID :
6437838
MDL Number :
MFCD01677956
Beilstein Registry :
1555726
SMILES :
C/C=C(\\C)/[[email protected]@H]([[email protected]](C)/C=C(\\C)/C=C/C/C(=C/CC1=C(C(=O)C(=C(N1)OC)OC)C)/C)O

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Certificate of Analysis

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Piericidin A  Product Citations

See how others have used Piericidin A. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 13 total

PMID: # 30201710  Benej, M.|Hong, X.|Vibhute, S.|Scott, S.|Wu, J.|Graves, E.|Le, QT.|Koong, AC.|Giaccia, AJ.|Yu, B.|Chen, CS.|Papandreou, I.|Denko, NC.| et al. 2018. Proc. Natl. Acad. Sci. U.S.A. 115: 10756-10761.

PMID: # 30043752  Divakaruni, AS.|Hsieh, WY.|Minarrieta, L.|Duong, TN.|Kim, KKO.|Desousa, BR.|Andreyev, AY.|Bowman, CE.|Caradonna, K.|Dranka, BP.|Ferrick, DA.|Liesa, M.|Stiles, L.|Rogers, GW.|Braas, D.|Ciaraldi, TP.|Wolfgang, MJ.|Sparwasser, T.|Berod, L.|Bensinger, SJ.|Murphy, AN.| et al. 2018. Cell Metab. 28: 490-503.e7.

PMID: # 25437199  Höllerhage, M. et al. 2014. PloS one. 9: e113557.

PMID: # 19128036  Murai, M. et al. 2009. Biochemistry. 48: 688-698.

PMID: # 19165199  van Norren, K. et al. 2009. Br. J. Cancer. 100: 311-314.

PMID: # 17722886  Pohl, T. et al. 2007. Biochemistry. 46: 10694-10702.

PMID: # 17474759  Murai, M. et al. 2007. Biochemistry. 46: 6409-6416.

PMID: # 16411776  Fernandes, AS. et al. 2006. Biochemistry. 45: 1002-1008.

PMID: # 16352837  Bayer, AS. et al. 2006. J. Bacteriol. 188: 211-222.

PMID: # 15767566  Weinstein, EA. et al. 2005. Proc. Natl. Acad. Sci. U.S.A. 102: 4548-4553.

Citations 1 to 10 of 13 total
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Rated 5 out of 5 by from Van Norren et al Van Norren et al. (PubMed ID 19165199) generated free radicals by inducing mitochondrial malfunction using Piericidin A to inhibit the respiratory chain. -SCBT Publication Review
Date published: 2015-06-02
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