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B6179

Sigma-Aldrich

Bongkrekic acid solution

from Pseudomonas cocovenenans, ≥95% (HPLC), solution, adenine nucleotide translocase inhibitor

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About This Item

Formule empirique (notation de Hill):
C28H38O7
Numéro CAS:
11076-19-0
Poids moléculaire :
486.60
Numéro MDL:
MFCD01729616
Code UNSPSC :
12352106
ID de substance PubChem :
24891898
Nomenclature NACRES :
NA.77

product name

Bongkrekic acid solution, from Pseudomonas cocovenenans, ≥95% (HPLC), ~1 mg/mL

Source biologique

Pseudomonas cocovenenans

Niveau de qualité

200

Pureté

≥95% (HPLC)

Forme

solution

Concentration

~1 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

CO[C@H](C/C=C\C=C\CC\C=C\C[C@H](C)\C=C\C(CC(O)=O)=C/C(O)=O)\C(C)=C/C=C(\C)C(O)=O

InChI

1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1

Clé InChI

SHCXABJSXUACKU-WUTQZGRKSA-N

Application

Bongkrekic acid solution has been used as an adenine nucleotide translocator (ANT) inhibitor to find out a different approach for the inhibition of oxidative phosphorylation in intact T98G cells. It has also been used as an inhibitor of the permeabilization transition pore complex (PTPC) pore and a tool to explore the role of PTPC in induction of apoptosis.

Actions biochimiques/physiologiques

An antiapoptotic agent, it protects against NMDA receptor induced neuronal apoptosis,­ extends cell survival in cells undergoing apoptosis following infection with viral vectors and abrogates apoptosis induced by hydrogen peroxide in T-cells. It is an inhibitor of adenine nucleotide translocase, which is a component of the mitochondrial permeability transition (MPT) pore complex. Bongkrekic acid prevents mitochondrial depolarization, swelling, rupture of mitochondrial outer membrane, and release of apoptogenic proteins such as cytochrome c. This phenomenon was observed during staurosporine induced apoptosis in Jurkat cells, in HepG2 undergoing apoptosis following TNF-α and ethanol.

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Autres remarques

The toxic principle of P. cocovenenans.

Forme physique

Solution in 0.01 M Tris buffer, pH 7.5.

Code de la classe de stockage

12 - Non Combustible Liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

I J Furlong et al.
Cell death and differentiation, 5(3), 214-221 (1999-04-14)
In order to determine whether disruption of mitochondrial function could trigger apoptosis in murine haematopoietic cells, we used the potassium ionophore valinomycin. Valinomycin induces apoptosis in the murine pre-B cell line BAF3, which cannot be inhibited by interleukin-3 addition or
J G Pastorino et al.
Hepatology (Baltimore, Md.), 31(5), 1141-1152 (2000-05-05)
In the present study, tumor necrosis factor-alpha (TNF-alpha) cytotoxicity is shown to be potentiated by ethanol exposure in vitro in the human hepatoma cell line, HepG2, and in rat primary hepatocytes. Exposure of HepG2 cells and primary hepatocytes for 48
A Dumont et al.
Oncogene, 18(3), 747-757 (1999-02-16)
Reactive oxygen species (ROS) play an important role in cell death induced by many different stimuli. This study shows that hydrogen peroxide-induced apoptosis in T-cells did not require tyrosine kinase p561ck, phosphatase CD45, the CD95 receptor and its associated Caspase-8.
J L Scarlett et al.
FEBS letters, 475(3), 267-272 (2000-06-28)
Cytochrome c release from mitochondria is central to apoptosis, but the events leading up to it are disputed. The mitochondrial membrane potential has been reported to decrease, increase or remain unchanged during cytochrome c release. We measured mitochondrial membrane potential
Ceramide-induced neuronal apoptosis is associated with dephosphorylation of Akt, BAD, FKHR, GSK-3beta, and induction of the mitochondrial-dependent intrinsic caspase pathway
Stoica B A, et al.
Molecular and Cellular Neurosciences, 22(3), 365-382 (2003)
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