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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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5 MG
$117.00
25 MG
$453.15

$117.00


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5 MG
$117.00
25 MG
$453.15

About This Item

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

$117.00


In StockDetails


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.[1] Hindered oncogenic MAPK (mitogen-activated protein kinase ) signaling leads to BAM15 induced mitochondrial apoptotic pathway activation.[2]
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

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

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)
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

Questions

1–2 of 2 Questions  
  1. This product comes in 100 bottles of 5 or 25mg each correct?

    1 answer
    1. The purchase of this item will include 1 bottle of 5mg or 25mg, depending on the package size ordered.

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  2. Is this product difficult to weigh? I have tried weighing the product from another company, and it stuck to the inside of the vial and the weigh boat. This made it very difficult to obtain an accurate mass.

    1 answer
    1. This product is packaged in a 4 mL amber glass vials. The lyophilization process or static may cause some adherence to the glass surface. The product can be spun down briefly to collect the vial contents in the bottom prior to weighing, Alternatively, the product may be dissolved in DMSO in the vial.

      To discuss further, we kindly ask you to navigate to the link https://www.sigmaaldrich.com/techservice, click on "Report Product Issues" under the Products Section with all the required information so that a member of our team can reach out to you to assist further. Thank you.

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