| Identification | Back Directory | [Name]
BONGKREKIC ACID | [CAS]
11076-19-0 | [Synonyms]
edioicacid
bongkrekicaci
BONGKREKIC ACID
bongkrekic acid solution
(r-(r*,s*(e,z,z,e,e,z,e)))--trimethyl
Bongkrekic Acid Solution (1.0mg/mL in 0.01 M Tris buffer, pH 7.5)
3-carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaen
2,4,8,10,14,18,20-docosaheptaenedioicacid,20-(carboxymethyl)-6-methoxy-2,5,17
(2E,4Z,6R,8Z,10E,14E,17S,18Z,20E)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
2,4,8,10,14,18,20-Docosaheptaenedioic acid, 20-(carboxymethyl)-6-methoxy-2,5,17-trimethyl-, (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)- | [EINECS(EC#)]
231-791-2 | [Molecular Formula]
C28H38O7 | [MDL Number]
MFCD01729616 | [MOL File]
11076-19-0.mol | [Molecular Weight]
486.6 |
| Chemical Properties | Back Directory | [Melting point ]
50-60° | [alpha ]
D25 +162.5° | [Boiling point ]
715.1±60.0 °C(Predicted) | [density ]
1.114±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO (up to 100 mg/ml) or in Water (up to 1 mg/ml). | [form ]
Lyophilized solid | [pka]
4.15±0.10(Predicted) | [color ]
Colorless to light yellow | [biological source]
Pseudomonas cocovenenans | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Bongkrekic acid (11076-19-0) is a p potent inhibitory ligand of the mitochondrial adenine nucleotide translocase (ANT).1?Inhibits mitochondrial permeability transition pore opening.2,3?Delivery of bongkrekic acid to the mitochondria prevents apoptosis in HeLa cells.4 | [Uses]
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. | [Definition]
ChEBI: A tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group. | [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. | [Enzyme inhibitor]
This toxic tricarboxylic acid (FWfree-acid = 486.61 g/mol; CAS 11076-19-0),
produced Pseudomonas cocovenenans, is a potent competitive inhibitor of
the mitochondrial ATP-ADP translocator, effectively blocking nucleotide
binding to the carrier . The name is derived from bongkrek, a moldy
coconut product produced in Indonesia. The toxin accumulates when P.
cocovenenans outgrows the mold. Klingenberg et al. investigated
bongkrekate binding to mitochondrial membrane to examine the reorienting
site mechanism. The inferred mode of inhibition requires bongkrekate to
bind to the single carrier site only from the inner face of the mitochondrial
membrane (i.e., the matrix side) ). They confirmed the pH-dependent
accumulation of [3H]bongkrekate inside the mitochondria which
superimposes onto the binding at carrier sites. By breaking the membrane
with Lubrol or sonication, binding to the carrier sites could be titrated, and a
Kd value of approximately 5 x 10–8 M was determined. The presence of ADP
or ATP increases the amount of binding but does not alter the Kd.
[35S]Atractylate is displaced by [3H]bongkrekate at a 1:1 molar ratio; this
displacement is dependent on ADP concentration with the Km = 0.5 x 10–6
M. See also Atractyloside The isomer known as isobongkrekic acid, which
has a cis-double bond at the dicarboxylic acid end of the molecule, has
similar biological activity. Target (s) : Adenine nucleotide translocator,
ADP/ATP carrier ; ATPase; bromelain, stem; papain; ficain,
or ficin. | [References]
1) Ziegler?et al. (1993),?The adenine nucleotide translocase modulates oligomycin-induced quenching of pyranine fluorescence in submitochondrial particles; J. Biol. Chem.,?268?25320
2) Marchetti?et al. (1996),?Mitochondrial permeability transition triggers lymphocyte apoptosis; J. Immunol.,?157?4830
3) Zamzami?et al. (1996),?Inhibitors of permeability transition interfere with the disruption of the mitochondrial transmembrane potential during apoptosis; FEBS Lett.,?384?53
4) Yamada?et al. (2013),?Mitochondrial delivery of bongkrekic acid using a MITO-Porter prevents the induction of apoptosis in human HeLa cells; J. Pharm. Sci.,?102?1008 |
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