SML1760
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
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
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
InChI
1S/C16H10F2N6O/c17-9-5-1-3-7-11(9)19-13-14(20-12-8-4-2-6-10(12)18)22-16-15(21-13)23-25-24-16/h1-8H,(H,19,21,23)(H,20,22,24)
InChI key
OEGJBRZAJRPPHL-UHFFFAOYSA-N
Biochem/physiol Actions
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.
BAM15 is a cell penetrant and potent uncoupler of oxidative phosphorylation in mitochondria.
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.
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 4
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)