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SML1760

Sigma-Aldrich

BAM15

≥98% (HPLC), powder, mitochondrial protonophore uncoupler

Synonym(s):

BAM 15, N5,N6-bis(2-Fluorophenyl)[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine

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About This Item

Empirical Formula (Hill Notation):
C16H10F2N6O
CAS Number:
Molecular Weight:
340.29
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

product name

BAM15, ≥98% (HPLC)

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

FC(C=CC=C1)=C1NC2=NC3=NON=C3N=C2NC4=CC=CC=C4F

Biochem/physiol Actions

BAM15 increases mitochondrial respiration rate and is also found to be less cytotoxic compared to other protonophore uncouplers such as carbonyl cyanide p-trifluoromethoxyphenylhydrazone. Hindered oncogenic MAPK (mitogen-activated protein kinase ) signaling leads to BAM15 induced mitochondrial apoptotic pathway activation.
BAM15 is a cell penetrant and potent uncoupler of oxidative phosphorylation in mitochondria that that does not depolarizes the plasma membrane. BAM15 protects mice from acute renal ischemic-reperfusion injury.

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dual suppression of inner and outer mitochondrial membrane functions augments apoptotic responses to oncogenic MAPK inhibition.
Serasinghe M N, et al.
Cell Death & Disease, 9(2), 29-29 (2018)
Brandon M Kenwood et al.
Bioorganic & medicinal chemistry letters, 25(21), 4858-4861 (2015-06-30)
Chemical mitochondrial uncouplers are lipophilic weak acids that transport protons into the mitochondrial matrix via a pathway that is independent of ATP synthase, thereby uncoupling nutrient oxidation from ATP production. These uncouplers have potential for the treatment of diseases such
Identification of a novel mitochondrial uncoupler that does not depolarize the plasma membrane.
Kenwood B M, et al.
Molecular Metabolism, 3(2), 114-123 (2014)
Brandon M Kenwood et al.
Molecular metabolism, 3(2), 114-123 (2014-03-19)
Dysregulation of oxidative phosphorylation is associated with increased mitochondrial reactive oxygen species production and some of the most prevalent human diseases including obesity, cancer, diabetes, neurodegeneration, and heart disease. Chemical 'mitochondrial uncouplers' are lipophilic weak acids that transport protons into
Keshav Kooragayala et al.
Investigative ophthalmology & visual science, 56(13), 8428-8436 (2016-01-10)
Cell death in neurodegeneration occurs at the convergence of diverse metabolic pathways. In the retina, a common underlying mechanism involves mitochondrial dysfunction since photoreceptor homeostasis and survival are highly susceptible to altered aerobic energy metabolism. We sought to develop an

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