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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

Fórmula empírica (Notação de Hill):
C28H38O7
Número CAS:
11076-19-0
Peso molecular:
486.60
Número MDL:
MFCD01729616
Código UNSPSC:
12352106
ID de substância PubChem:
24891898
NACRES:
NA.77

Nome do produto

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

fonte biológica

Pseudomonas cocovenenans

Nível de qualidade

200

Ensaio

≥95% (HPLC)

Formulário

solution

concentração

~1 mg/mL

Condições de expedição

wet ice

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

SHCXABJSXUACKU-WUTQZGRKSA-N

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Outras notas

The toxic principle of P. cocovenenans.

forma física

Solution in 0.01 M Tris buffer, pH 7.5.

Código de classe de armazenamento

12 - Non Combustible Liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
117M4123V
119M4029V
14190508
108M4030V
14180307

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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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Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

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