ChemicalBook > CAS DataBase List > PIERICIDIN A

PIERICIDIN A

Product Name: PIERICIDIN A
CAS No.: 2738-64-9
Chemical Name: PIERICIDIN A
Synonyms: SN 198E;IT-143D;piericidin;piericidinea;PIERICIDIN A;PIERICIDIN A1;SHAOGUAMYCIN B;SHAOGUANMYCIN B;piericidin(sub1);Piericidin A (Synonyms: AR-054)
CBNumber: CB9758229
Molecular Formula: C25H37NO4
Formula Weight: 415.57
MOL File: 2738-64-9.mol

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PIERICIDIN A Property

Boiling point:: 614.9±55.0 °C(Predicted)
Density: 1.044±0.06 g/cm3(Predicted)
Flash point:: 85 °C
storage temp.: 2-8°C
solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
form: liquid
pka: 5.21±0.33(Predicted)
color: green-yellow
Stability:: 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.
InChIKey: BBLGCDSLCDDALX-LKGBESRRSA-N
SMILES: C1(C/C=C(\C)/C/C=C/C(/C)=C/[C@@H](C)[C@@H](O)/C(/C)=C/C)=NC(OC)=C(OC)C(O)=C1C

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Safety

Hazard Codes: T+,Xn
Risk Statements: 26/27/28-20/21/22
Safety Statements: 28-36/37-45
RIDADR: UN 3382 6.1/PG 1
WGK Germany: 3
RTECS: YD4588000
F: 3-10
HS Code: 2933399990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 15379
Product name: Piericidin A
Purity: ≥95%
Packaging: 1mg
Price: $135
Updated: 2024/03/01

Cayman Chemical

Product number: 15379
Product name: Piericidin A
Purity: ≥95%
Packaging: 5mg
Price: $641
Updated: 2024/03/01

Usbiological

Product number: P4155
Product name: Piericidin A
Packaging: 1mg
Price: $408
Updated: 2021/12/16

TRC

Product number: P991778
Product name: PiericidinA
Packaging: 2.5mg
Price: $1050
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb546184
Product name: Piericidin A
Purity: >98%
Packaging: 200ug
Price: $136
Updated: 2021/12/16

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PIERICIDIN A Chemical Properties,Usage,Production

Description

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

Uses

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.

Uses

Piericidin A is an antibiotic and a member of the Class I inhibitors that acts as an effective inhibitor of Complex I.

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].

Enzyme inhibitor

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.

References

[1] ROMANA FATO . Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species[J]. Biochimica et Biophysica Acta-Bioenergetics, 2009, 1787 5: Pages 384-392. DOI:10.1016/j.bbabio.2008.11.003
[2] XUEFENG ZHOU William F. The unique chemistry and biology of the piericidins[J]. Journal of Antibiotics, 2016, 69 8: 582-593. DOI:10.1038/ja.2016.71
[3] ROBERT D. BONGARD Marilyn P M Mary I Townsley. 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)[J]. Free Radical Biology and Medicine, 2015, 79: Pages 69-77. DOI:10.1016/j.freeradbiomed.2014.09.030
[4] KANG KWANG LEE . Isoniazid-induced cell death is precipitated by underlying mitochondrial complex I dysfunction in mouse hepatocytes[J]. Free Radical Biology and Medicine, 2013, 65: Pages 584-594. DOI:10.1016/j.freeradbiomed.2013.07.038
[5] WON-SEOK CHOI Zhengui X Richard D Palmiter. Loss of mitochondrial complex I activity potentiates dopamine neuron death induced by microtubule dysfunction in a Parkinson’s disease model.[J]. Journal of Cell Biology, 2011, 192 5: 873-882. DOI:10.1083/jcb.201009132
[6] JI-HWAN HWANG. Etoposide-resistant HT-29 human colon carcinoma cells during glucose deprivation are sensitive to piericidin A, a GRP78 down-regulator[J]. Journal of Cellular Physiology, 2007, 215 1: 243-250. DOI:10.1002/jcp.21308

PIERICIDIN A Preparation Products And Raw materials

Raw materials

Preparation Products

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PIERICIDIN A Suppliers

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View Lastest Price from PIERICIDIN A manufacturers

Career Henan Chemical Co

Product: PIERICIDIN A 2738-64-9
Price: US $1.00/g
Min. Order: 1g
Purity: ≥98%
Supply Ability: g/kg/Ton
Release date: 2019-12-25

2738-64-9, PIERICIDIN ARelated Search:

Amphotericin B Antibiotic agar NO.2 High pH, Antibiotic agar NO.3 2-METHOXY-5-PICOLINE TRANS,CIS-3,6-NONADIEN-1-OL 2,3-Dihydroxypyridine PIERICIDIN A 3,4-Dihydroxypyridine 2,3-Dimethoxypyridine 2,4-DIHYDROXY-6-METHYLPYRIDINE Antibiotic agar NO.1 Low PH Antibiotic Α-PROTEIN Chlortetracycline Antibiotic agar NO.1 High pH Antibiotic agar NO.2 Low pH 2(1H)-Pyridinone,4-hydroxy-5-methyl-(9CI) 4-Hydroxy-2,3-dimethoxypyridine

,5,7,11-tetramethyl-,(all-e)-(4s,5s)-

2,6,9,11-tridecatetraen-4-ol,13-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3

piericidin

piericidin(sub1)

piericidinea

SN 198E

SHAOGUAMYCIN B

SHAOGUANMYCIN B

PIERICIDIN A

PIERICIDIN A1

2,6,9,11-TRIDECATETRAEN-4-OL,13-(4-HYDROX-5,6-DIMETHOXY-3-METHYL-2-PYRIDYL)-3,5,7,11-TETRAMETHYL-(ALL-E)-(4R,5R)-(8CL)

Piericidin A from Streptomyces mobaraensis

PENICILLIN-STREPTOMYCIN (200X PEN-STREP)

piericidin a from microbial source

Piericidin A1, Shaoguamycin B, SN 198E, 2,6,9,11-Tridecatetraen-4-ol,13-(4-hydrox-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-(all-E)-(4R,5R)-(8Cl), 4-Pyridinol,2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy- [R-[R*,R*-(all-E)]]-3-methyl-

(2E,4S,5S,6E,8E,11E)-13-(5,6-Dimethoxy-4-hydroxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-2,6,8,11-tridecatetren-4-ol

IT-143D

4-PYRIDINOL,2-(10-HYDROXY-3,7,9,11-TETRAMETHYL-2,5,7,11-TRIDECATETRAENYL)-5,6-DIMETHOXY-, [R-[R*,R*-(ALL-E)]]-3-METHYL-

ShaoguanMycin B, MT 1882-I, SN 198E, IT 143D, Piericidin A1

2,6,9,11-Tridecatetraen-4-ol,13-(4-hydrox-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-(all-E)-(4R,5R)

4-Pyridinol,2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy- [R-[R*,R*-(all-E)]]-3-methyl-

2-[(2E,4E,7E,9S,10S,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,4,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one

4-Pyridinol, 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-

2-((2E,5E,7E,9R,10R,11E)-10-Hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl)-5,6-dimethoxy-3-methylpyridin-4-ol

Piericidin A (Synonyms: AR-054)

2738-64-9

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