BONGKREKIC ACID
- CAS No.
- 11076-19-0
- Chemical Name:
- BONGKREKIC ACID
- Synonyms
- edioicacid;bongkrekicaci;BONGKREKIC ACID;bongkrekic acid solution;Bongkrekic Acid (AS 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
- CBNumber:
- CB4140241
- Molecular Formula:
- C28H38O7
- Molecular Weight:
- 486.6
- MDL Number:
- MFCD01729616
- MOL File:
- 11076-19-0.mol
- MSDS File:
- SDS
| 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) |
| 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. |
| FDA UNII | L7V4I673D2 |
BONGKREKIC ACID price More Price(5)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | B6179 | Bongkrekic acid solution from Pseudomonas cocovenenans, ≥95% (HPLC), ~1?mg/mL | 11076-19-0 | 0.5mg | $599 | 2024-03-01 | Buy |
| TRC | B699841 | BongkrekicAcidSolution(1.0mg/mLin0.01MTrisbuffer,pH7.5) | 11076-19-0 | 0.1ml | $635 | 2021-12-16 | Buy |
| ChemScene | CS-0129190 | Bongkrekicacid | 11076-19-0 | 500ug | $850 | 2021-12-16 | Buy |
| Biorbyt Ltd | orb546110 | bongkrekic acid >98% | 11076-19-0 | 100μg | $348.5 | 2021-12-16 | Buy |
BONGKREKIC ACID Chemical Properties,Uses,Production
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
BONGKREKIC ACID Preparation Products And Raw materials
Raw materials
Preparation Products
BONGKREKIC ACID Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32715 | 60 |
| BOC Sciences | 16314854226; +16314854226 | inquiry@bocsci.com | United States | 19743 | 58 |
| Aladdin Scientific | +1-+1(833)-552-7181 | sales@aladdinsci.com | United States | 52927 | 58 |
| Qingdao IniKem BioPharmaTech Co.,Ltd | 0532-58268780 18653202088 | sales@inikem.com | China | 290 | 55 |
| Sinopharm Chemical Reagent Co,Ltd. | 86-21-63210123 | sj_scrc@sinopharm.com | China | 9823 | 79 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4428 | 55 |
| ChemStrong Scientific Co.,Ltd | 0755-0755-66853366 13670046396 | sales@chem-strong.com | China | 17993 | 56 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51471 | 80 |
| Alta Scientific Co., Ltd. | 022-6537-8550 15522853686 | sales@altasci.com.cn | China | 4515 | 55 |
| Shenzhen Regent Biochemical Technology Co., Ltd. | 0755-0755-85201366 18938635012 | sales@regentsciences.com | China | 9294 | 58 |