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B6179 Sigma-Aldrich

Bongkrekic acid solution

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

  • CAS Number 11076-19-0

  • Empirical Formula (Hill Notation) C28H38O7

  • Molecular Weight 486.60

  •  MDL number MFCD01729616

  •  PubChem Substance ID 24891898

  •  NACRES NA.77

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Properties

Related Categories A to C, Adenine nucleotide translocase, Apoptosis Inhibitors, Apoptosis and Cell Cycle, B,
Quality Level   200
biological source   Pseudomonas cocovenenans
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

Description

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.

Packaging

0.5 mg in glass bottle

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

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...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Clinical, Diseases, Ligands, Neurodegenerative Diseases

Discover Bioactive Small Molecules for Cell Cycle Research

In proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during t...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Cell division, Cell proliferation, DNA replication, Diseases, Genetic

Peer-Reviewed Papers
15

References

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