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 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.
BAM15 is a cell penetrant and potent uncoupler of oxidative phosphorylation in mitochondria.
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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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML1760-5MG | 04061832275154 |
| SML1760-25MG | 04061832275147 |