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B6179

Sigma-Aldrich

Bongkrekic acid solution

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

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0.5 MG
$585.20

About This Item

Empirical Formula (Hill Notation):
C28H38O7
CAS Number:
11076-19-0
Molecular Weight:
486.60
MDL number:
MFCD01729616
UNSPSC Code:
12352106
PubChem Substance ID:
24891898
NACRES:
NA.77

$585.20

List Price$616.00
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

Product Name

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

biological source

Pseudomonas cocovenenans

Quality Level

200

assay

≥95% (HPLC)

form

solution

concentration

~1 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI key

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.[1] 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.[2]

Biochem/physiol Actions

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.

Features and Benefits

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.

Other Notes

The toxic principle of P. cocovenenans.

Physical form

Solution in 0.01 M Tris buffer, pH 7.5.

Storage Class

12 - Non Combustible Liquids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000241727
14161102
117M4123V
14180307
14170711

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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)
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
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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