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Merck
CN

96861

Sigma-Aldrich

Piericidin A from Streptomyces mobaraensis

≥90.0% (HPLC), liquid, green-yellow

Synonym(s):

Shaoguanmycin B

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About This Item

Empirical Formula (Hill Notation):
C25H37NO4
CAS Number:
2738-64-9
Molecular Weight:
415.57
MDL number:
MFCD01677956
UNSPSC Code:
12352200
PubChem Substance ID:
329770534

Key Documents

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Assay

≥90.0% (HPLC)

form

liquid

loss

<10% loss on drying

color

green-yellow

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

2-8°C

SMILES string

COc1nc(C\C=C(/C)C\C=C\C(C)=C\[C@@H](C)[C@@H](O)\C(C)=C\C)c(C)c(O)c1OC

InChI

1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1

InChI key

BBLGCDSLCDDALX-LKGBESRRSA-N

Other Notes

Neurotoxin for the respiratory chain

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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R R Ramsay et al.
The Biochemical journal, 273(Pt 2), 481-484 (1991-01-15)
1-Methyl-4-phenylpyridinium (MPP+), the neurotoxic bioactivation product of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), interrupts mitochondrial electron transfer at the NADH dehydrogenase-ubiquinone junction, as do the respiratory chain inhibitors rotenone, piericidin A and barbiturates. Proof that these classical respiratory chain inhibitors and MPP+ react at
T P Singer et al.
Biochimica et biophysica acta, 1187(2), 198-202 (1994-08-30)
This article summarizes recent studies in the authors' and other laboratories of selective inhibitors acting at the 'rotenone' site and at the Q binding site in the NADH-Q oxidoreductase segment of the respiratory chain. A wide array of inhibitors act
Martin J Schnermann et al.
Journal of the American Chemical Society, 128(36), 11799-11807 (2006-09-07)
Full details of the total synthesis of piericidin A1 and B1 and its extension to the preparation of a series of key analogues are described including ent-piericidin A1 (ent-1), 4'-deshydroxypiericidin A1 (58), 5'-desmethylpiericidin A1 (73), 4'-deshydroxy-5'-desmethylpiericidin A1 (75), and the
Nobuhiro Ikezawa et al.
Bioscience, biotechnology, and biochemistry, 66(9), 1925-1929 (2002-10-29)
The effects of several respiration inhibitors on photosystem II (PS II) were investigated. Among the agents tested, piericidin A and thenoyltrifluoroacetone (TTFA) inhibited the photosynthetic electron transport of spinach as measured from chlorophyll (Chl) fluorescence parameters (Fm'-F)/Fm' and Fv/Fm. Using
Romana Fato et al.
Biochimica et biophysica acta, 1787(5), 384-392 (2008-12-09)
We have investigated the production of reactive oxygen species (ROS) by Complex I in isolated open bovine heart submitochondrial membrane fragments during forward electron transfer in presence of NADH, by means of the probe 2',7'-Dichlorodihydrofluorescein diacetate. ROS production by Complex
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