Bongkrekic acid

Names

[ Name ]:
Bongkrekic acid

[Synonym ]:
Bongkrekic Acid, Triammonium Salt
BONGKREKIC ACID
Bongkrekic acid solution

Biological Activity

[Description]:

Bongkrekic acid is a mitochondrial toxin secreted by the bacteria Pseudomonas cocovenenans[1]. Bongkrekic acid specific ligand for mitochondrial adenine nucleotide translocase (ANT) rather than the electron transport chain. Bongkrekic acid has to cross the mitochondrial inner membrane to produce its inhibitory effect on ADP/ATP transport[2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Membrane Transporter/Ion Channel >> ATP Synthase

[In Vitro]

Bongkrekic acid (0-50 μM; 48 hours) stimulated formazan formation in MDA-MB-231, MCF-7 and LTED cells with EC50 of 34.14 μM, >50 μM and 2.58 μM, respectively. Bongkrekic acid (0.1-25 μM; 48 hours) decreases the living cell numbers in LTED cells and parent MCF-7 cells in a dose-dependent manner[1].

[References]

[1]. Mehruba Anwar, et al. Bongkrekic Acid-a Review of a Lesser-Known Mitochondrial Toxin. J Med Toxicol. 2017 Jun;13(2):173-179.

[2]. C Dahout-Gonzalez, et al. Molecular, functional, and pathological aspects of the mitochondrial ADP/ATP carrier. Physiology (Bethesda)

[3]. Shuso Takeda, et al. Bongkrekic Acid as a Warburg Effect Modulator in Long-term Estradiol-deprived MCF-7 Breast Cancer Cells. Anticancer Res

Chemical & Physical Properties

[ Density]:
1.114g/cm3

[ Boiling Point ]:
715.1ºC at 760mmHg

[ Melting Point ]:
50-60°

[ Molecular Formula ]:
C₂₈H₃₈O₇

[ Molecular Weight ]:
486.59700

[ Flash Point ]:
231ºC

[ Exact Mass ]:
486.26200

[ PSA ]:
121.13000

[ LogP ]:
5.88560

[ Appearance of Characters ]:
Lyophilized solid

[ Index of Refraction ]:
1.545

[ Storage condition ]:
-20°C

[ Water Solubility ]:
Soluble in DMSO (up to 100 mg/ml) or in Water (up to 1 mg/ml).

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JR1230000

CHEMICAL NAME :: 2,4,8,10,14,18,20-Docosaheptaenedioic acid, 20-(carboxymethyl)-6-methoxy-2,5,17-trimethyl-, (R-(R*,S*(E,Z,Z,E,E,Z,E)))-

CAS REGISTRY NUMBER :: 11076-19-0

LAST UPDATED :: 199707

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C28-H38-O7

MOLECULAR WEIGHT :: 486.66

WISWESSER LINE NOTATION :: QVY1&U2UY1&YO1&2U2U4U2Y1&1U1Y1VQU1VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1410 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TETRAB Tetrahedron. (Pergamon Press Inc., Maxwell House, Fairview Park, Elm sford, NY 10523) V.1- 1957- Volume(issue)/page/year: 26,5993,1970

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ RIDADR ]:
NONH for all modes of transport

Articles

Changes in mitochondrial membrane potential during staurosporine-induced apoptosis in Jurkat cells.

FEBS Lett. 475 , 267, (2000)

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 unc...

BCL-2 family members and the mitochondria in apoptosis.

Genes Dev. 13 , 1899, (1999)

Hydrogen peroxide-induced apoptosis is CD95-independent, requires the release of mitochondria-derived reactive oxygen species and the activation of NF-kappaB.

Oncogene 18 , 747, (1999)

Reactive oxygen species (ROS) play an important role in cell death induced by many different stimuli. This study shows that hydrogen peroxide-induced apoptosis in T-cells did not require tyrosine kina...

Related Compounds

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