B6179

Bongkrekic acid solution

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

• 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

Properties

• 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

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.

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 Information

• Storage Class Code: 12 - Non Combustible Liquids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves