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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

Formula empirica (notazione di Hill):
C28H38O7
Numero CAS:
11076-19-0
Peso molecolare:
486.60
Numero MDL:
MFCD01729616
Codice UNSPSC:
12352106
ID PubChem:
24891898
NACRES:
NA.77

product name

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

Origine biologica

Pseudomonas cocovenenans

Livello qualitativo

200

Saggio

≥95% (HPLC)

Forma fisica

solution

Concentrazione

~1 mg/mL

Condizioni di spedizione

wet ice

Temperatura di conservazione

−20°C

Stringa SMILE

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
SHCXABJSXUACKU-WUTQZGRKSA-N

Applicazioni

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.

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Altre note

The toxic principle of P. cocovenenans.

Stato fisico

Solution in 0.01 M Tris buffer, pH 7.5.

Codice della classe di stoccaggio

12 - Non Combustible Liquids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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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)
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
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.
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
A J Mastrangelo et al.
Biotechnology and bioengineering, 65(3), 298-305 (1999-09-15)
Viral expression systems allow for the rapid production of large amounts of recombinant protein in cell culture. In particular, Sindbis virus vectors now exist that make possible the expression of a variety of heterologous proteins in mammalian culture systems. Unfortunately
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