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MedKoo Cat#: 522443 | Name: BAM15
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

BAM15 is a potent and selective mitochondrial uncoupler or protonophore. 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 as obesity, Parkinson’s disease, and aging.

Chemical Structure

BAM15
BAM15
CAS#210302-17-3

Theoretical Analysis

MedKoo Cat#: 522443

Name: BAM15

CAS#: 210302-17-3

Chemical Formula: C16H10F2N6O

Exact Mass: 340.0884

Molecular Weight: 340.29

Elemental Analysis: C, 56.47; H, 2.96; F, 11.17; N, 24.70; O, 4.70

Price and Availability

Size Price Availability Quantity
25mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to Ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 2,650.00 Ready to ship
1g USD 3,850.00 Ready to ship
2g USD 5,950.00 2 Weeks
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Related CAS #
No Data
Synonym
BAM15; BAM-15; BAM 15.
IUPAC/Chemical Name
N5,N6-bis(2-fluorophenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine
InChi Key
OEGJBRZAJRPPHL-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
FC1=CC=CC=C1NC2=NC3=NON=C3N=C2NC4=C(C=CC=C4)F
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
BAM 15 is a mitochondrial protonophore uncoupler and an oxidative phosphorylation (OXPHOS) uncoupler.
In vitro activity:
The effects of BAM15 was measured versus FCCP on plasma membrane electrophysiology using whole cell voltage and current clamp recordings. As expected, under voltage clamp conditions at a holding potential of −70 mV, FCCP induced an inward current that was dose-dependent and associated with an increase in conductance (Figure 4A–F). In contrast, BAM15 elicited no appreciable change in current in the same cells. Under current clamp conditions, FCCP caused reversible and repeatable plasma membrane depolarization, whereas BAM15 had no effect (Figure 4G and H). The differential effects of BAM15 and FCCP on plasma membrane properties were independent of the order of uncoupler application (not shown). Furthermore, BAM15-treated cells were more viable than FCCP-treated cells when administered across a broad dosing range up to 50 μM (Suppl. Figure 6). These data indicate that BAM15 does not share the adverse plasma membrane effects that may contribute to cytotoxicity. Reference: Mol Metab. 2013 Nov 28;3(2):114-23. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24634817/
In vivo activity:
To determine the efficacy and feasibility of BAM15 in vivo, 10‐week‐old male diet‐induced obese (DIO) C57BL/6J mice were randomized to 3 weeks of CTRL (60% HFD) or BAM15 (60% HFD + 0.1% w/w BAM15). Ad libitum consumption of BAM15 resulted in consumption of ~85 mg/kg/day (Fig EV2A), with peak serum concentrations of ~5 μM and a half‐life of ~3 h (Fig 4A). Further assessment revealed primary distribution into adipose tissue depots and to lesser extent, liver, heart, and kidneys (Figs 4B and EV2B). By day 9, BAM15 animals displayed reduced body weight relative to control (Figs 4C and EV2C, and EV3A), an effect that persisted throughout the remainder of the treatment period. BAM15 did not affect daily (Fig EV2D and E) or cumulative food intake until day 20 (Fig 4D), at which point a mean difference in body weight of 7.5 g was observed. Neither acute intraperitoneal injection (Fig 4E) of BAM15 nor chronic oral administration (Figs 4F and EV2F) altered body temperature. Furthermore, acute oral administration of BAM15 did not alter tail heat dissipation (Fig EV2G and H). Unlike CTRL, which gained both fat and lean mass during the treatment period, BAM15 animals displayed reduced fat mass with no change in lean mass compared with baseline (Fig 4G and H). The reductions in fat mass were consistent with marked reductions in gonadal white adipose tissue (gWAT), inguinal WAT (iWAT), retroperitoneal WAT (rpWAT), and brown adipose tissue (BAT) depot weights (Fig EV3). However, there were no differences in muscle depots, such as the mixed gastrocnemius or heart (Fig EV3). In addition to adipose depots, liver weight was reduced in BAM15‐treated animals (Fig EV3), along with fasting plasma glucose and insulin (Fig 4I and J). Given the reductions in fasting glucose and insulin, glycemic control was then assessed by intraperitoneal glucose tolerance testing (IPGTT). It was observed that glucose clearance was improved in BAM15 animals relative to CTRL (Figs 4K and L and EV2I). To determine whether alterations in energy expenditure explained the reductions in body weight and adiposity, animals were placed in a metabolic chamber and examined over a 7‐day period. Oxygen consumption and total daily energy expenditure were increased (Fig 4M and N), whereas the respiratory exchange ratio (RER) was decreased (Fig 4O) in BAM15‐treated animals. Notably, the daily effect on energy expenditure was driven by changes in dark phase expenditure and consumption. In addition to energy expenditure, BAM15 preserved locomotor function, which decreased from baseline in CTRL animals (Fig EV2J and K). Cumulative water consumption was unaffected by BAM15 (Fig EV2L). To confirm that the improvements in weight regulation were attributable to increased energy expenditure, fecal lipid content was measured and no differences between groups was observed (Fig 4P). Taken together, these data suggest that BAM15 protects against diet‐induced obesity and improves glycemic control by increasing energy expenditure and reducing adiposity. Reference: EMBO Mol Med. 2020 Jul 7;12(7):e12088. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/32519812/
Solvent mg/mL mM
Solubility
DMSO 20.0 58.80
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 340.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Kenwood BM, Weaver JL, Bajwa A, Poon IK, Byrne FL, Murrow BA, Calderone JA, Huang L, Divakaruni AS, Tomsig JL, Okabe K, Lo RH, Cameron Coleman G, Columbus L, Yan Z, Saucerman JJ, Smith JS, Holmes JW, Lynch KR, Ravichandran KS, Uchiyama S, Santos WL, Rogers GW, Okusa MD, Bayliss DA, Hoehn KL. Identification of a novel mitochondrial uncoupler that does not depolarize the plasma membrane. Mol Metab. 2013 Nov 28;3(2):114-23. doi: 10.1016/j.molmet.2013.11.005. PMID: 24634817; PMCID: PMC3953706. 2. Axelrod CL, King WT, Davuluri G, Noland RC, Hall J, Hull M, Dantas WS, Zunica ER, Alexopoulos SJ, Hoehn KL, Langohr I, Stadler K, Doyle H, Schmidt E, Nieuwoudt S, Fitzgerald K, Pergola K, Fujioka H, Mey JT, Fealy C, Mulya A, Beyl R, Hoppel CL, Kirwan JP. BAM15-mediated mitochondrial uncoupling protects against obesity and improves glycemic control. EMBO Mol Med. 2020 Jul 7;12(7):e12088. doi: 10.15252/emmm.202012088. Epub 2020 Jun 10. PMID: 32519812; PMCID: PMC7338798.
In vivo protocol:
1. Kenwood BM, Weaver JL, Bajwa A, Poon IK, Byrne FL, Murrow BA, Calderone JA, Huang L, Divakaruni AS, Tomsig JL, Okabe K, Lo RH, Cameron Coleman G, Columbus L, Yan Z, Saucerman JJ, Smith JS, Holmes JW, Lynch KR, Ravichandran KS, Uchiyama S, Santos WL, Rogers GW, Okusa MD, Bayliss DA, Hoehn KL. Identification of a novel mitochondrial uncoupler that does not depolarize the plasma membrane. Mol Metab. 2013 Nov 28;3(2):114-23. doi: 10.1016/j.molmet.2013.11.005. PMID: 24634817; PMCID: PMC3953706. 2. Axelrod CL, King WT, Davuluri G, Noland RC, Hall J, Hull M, Dantas WS, Zunica ER, Alexopoulos SJ, Hoehn KL, Langohr I, Stadler K, Doyle H, Schmidt E, Nieuwoudt S, Fitzgerald K, Pergola K, Fujioka H, Mey JT, Fealy C, Mulya A, Beyl R, Hoppel CL, Kirwan JP. BAM15-mediated mitochondrial uncoupling protects against obesity and improves glycemic control. EMBO Mol Med. 2020 Jul 7;12(7):e12088. doi: 10.15252/emmm.202012088. Epub 2020 Jun 10. PMID: 32519812; PMCID: PMC7338798.
1: Shukla S, Lee JS, Park HK, Yoo JA, Hong SY, Kim JK, Kim M. Effect of Novel Starter Culture on Reduction of Biogenic Amines, Quality Improvement, and Sensory Properties of Doenjang, a Traditional Korean Soybean Fermented Sauce Variety. J Food Sci. 2015 Aug;80(8):M1794-803. doi: 10.1111/1750-3841.12942. Epub 2015 Jul 3. PubMed PMID: 26147854. 2: Kenwood BM, Calderone JA, Taddeo EP, Hoehn KL, Santos WL. Structure-activity relationships of furazano[3,4-b]pyrazines as mitochondrial uncouplers. Bioorg Med Chem Lett. 2015 Nov 1;25(21):4858-61. doi: 10.1016/j.bmcl.2015.06.040. Epub 2015 Jun 16. PubMed PMID: 26119501. 3: Kenwood BM, Weaver JL, Bajwa A, Poon IK, Byrne FL, Murrow BA, Calderone JA, Huang L, Divakaruni AS, Tomsig JL, Okabe K, Lo RH, Cameron Coleman G, Columbus L, Yan Z, Saucerman JJ, Smith JS, Holmes JW, Lynch KR, Ravichandran KS, Uchiyama S, Santos WL, Rogers GW, Okusa MD, Bayliss DA, Hoehn KL. Identification of a novel mitochondrial uncoupler that does not depolarize the plasma membrane. Mol Metab. 2013 Nov 28;3(2):114-23. doi: 10.1016/j.molmet.2013.11.005. eCollection 2014 Apr. PubMed PMID: 24634817; PubMed Central PMCID: PMC3953706. 4: Kunapuli P, Lee S, Zheng W, Alberts M, Kornienko O, Mull R, Kreamer A, Hwang JI, Simon MI, Strulovici B. Identification of small molecule antagonists of the human mas-related gene-X1 receptor. Anal Biochem. 2006 Apr 1;351(1):50-61. Epub 2006 Feb 3. PubMed PMID: 16510108.