PIERICIDIN A Struktur

PIERICIDIN A

Bezeichnung:PIERICIDIN A

CAS-Nr2738-64-9

Englisch Name:PIERICIDIN A

CBNumberCB9758229

SummenformelC25H37NO4

Molgewicht415.57

MOL-Datei2738-64-9.mol

PIERICIDIN A physikalisch-chemischer Eigenschaften

Siedepunkt	614.9±55.0 °C(Predicted)
Dichte	1.044±0.06 g/cm3(Predicted)
Flammpunkt	85 °C
storage temp.	2-8°C
Löslichkeit	Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
pka	5.21±0.33(Predicted)
Aggregatzustand	liquid
Farbe	green-yellow
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or Ethanol may be stored at -20°C for up to 1 month.

Sicherheit

Kennzeichnung gefährlicher	T+,Xn
R-Sätze:	26/27/28-20/21/22
S-Sätze:	28-36/37-45
RIDADR	UN 3382 6.1/PG 1
WGK Germany	3
RTECS-Nr.	YD4588000
F	3-10
HS Code	2933399990

Gefahreninformationscode (GHS)

PIERICIDIN A Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Piericidin A (2738-64-9) is a potent inhibitor of the mitochondrial and bacterial type I NADH-ubiquinone oxidoreductase (complex I).1?Piericidin A is a ubiquinone analog which binds to the ubiquinone binding site of the enzyme.2?It is an extremely useful tool for exploring the role of complex I in mitochondrial function in both normal and pathophysiology.3-5?Prevents upregulation of GRP78 and induces cell death in glucose-deprived, etoposide-resistant HT-29 cells (IC50=7.7 nM).6
Verwenden
Piericidin A is an antibiotic and a member of the Class I inhibitors that acts as an effective inhibitor of Complex I.
Verwenden
Piericidin A is the major analogue of a family of pyridyl antibiotics isolated from selected Streptomyces species. It is a specific, potent inhibitor of NADH-ubiquinone oxidoreductase (Complex I) that binds to ubiquinone binding site(s). Piericidin A inhibits both mitochondrial and bacterial NADH-ubiquinone oxidoreductases, binding close to NUOD-NUOB interface.
Definition
ChEBI: Piericidin A is a member of the class of monohydroxypyridines that acts as an irreversible mitochondrial Complex I inhibitor that strongly associates with ubiquinone binding sites in both mitochondrial and bacterial forms of NADH:ubiquinone oxidoreductase It has a role as a mitochondrial respiratory-chain inhibitor, an EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor, an antimicrobial agent and a bacterial metabolite. It is a monohydroxypyridine, a member of methylpyridines, an aromatic ether and a secondary allylic alcohol.
Biochem/physiol Actions
Piericidin A (PA), an insecticidal metabolite of Streptomyces mobaraensis is a potential quorum-sensing inhibitors (QSIs) that can destroy the expression of the virulence genes of Erwinia carotovora subsp. atroseptica (Eca). Hence it may be used as control agents of soft rot disease on potato tubers.
in vitro
previous study found that piericidin a could inhibit the electron transport system at two sites. piericidin a specifically reacted at very low concentrations at a site near the reduced nadh dehydrogenase. at high concentrations, piericidin a inhibited the succinic dehydrogenase system, and the inhibition could be partially reversed by coenzyme q. moreover, it was found that both the succinate and nadh oxidase system were inhibited at high levels of piericidin a [1].
in vivo
animal study was performed to evaluate the effect of piericidin a and antagonistic effect of vitamin k3 on respiration, blood pressure and heart rate in rats. results showed that 0.167 mg/kg of piericidin a increased the respiratory rate and the lowered blood pressure rapidly. furthermore, vitamin k3 (10-40 mg/kg) could restore the responses to piericidin a in rats [2].
Enzyminhibitor
This reduced antibiotic (FW = 423.64 g/mol; CAS 2738-64-9; Soluble in ethanol, methanol, DMF or DMSO) is a structural analogue of ubiquinone and a partially competitive inhibitor of bacterial and mitochondrial Type-I NADH-ubiquinone oxidoreductases (or Complex I). Octahydropiericidin A also inhibits glucose dehydrogenase.
Einzelnachweise
1) Fato?et al.?(2009),?Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species; Biochim. Biophys. Acta,?1787?384 2) Zhou and Fenical (2016),?The unique chemistry and biology of the piericidins; J. Antibiot. (Tokyo),?69?582 3) Bongard?et al.?(2015),?The effects of mitochondrial complex I blockade on ATP and permeability in rat pulmonary microvascular endothelial cells in culture (PMVEC) are overcome by coenzyme Q1 (CoQ1); Free Radic. Biol. Med.,?79?69 4) Lee?et al.?(2013),?Isoniazid-induced cell death is precipitated by underlying mitochondrial complex I dysfunction in mouse hepatocytes; Free Radic. Biol. Med.,?65?584 5) Choi?et al.?(2011),?Loss of mitochondrial complex I activity potentiates dopamine neuron death induced by microtubule dysfunction in a parkinson’s disease model; J. Cell Biol.,?192?873 6) Hwang?et al.?(2008),?Etoposide-resistant HT-29 human colon carcinoma cells during glucose deprivation are sensitive to piericidin A, a GRP78 down regulator; J. Cell Physiol.,?215?243

PIERICIDIN A Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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