BAM15

BAM15
Names
	Preferred IUPAC name N5,N6-Bis(2-fluorophenyl)[2,1,3]oxadiazolo[4,5-b]pyrazine-5,6-diamine
Identifiers
CAS Number	210302-17-3 [ChemSpider];
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3627755;
ChemSpider	491757;
PubChem CID	565708;
	InChI 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) Key: OEGJBRZAJRPPHL-UHFFFAOYSA-N;
	SMILES C1=CC=C(C(=C1)NC2=NC3=NON=C3N=C2NC4=CC=CC=C4F)F;
Properties
Chemical formula	C16H10F2N6O
Molar mass	340.294 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

BAM15 is a novel mitochondrial protonophore uncoupler capable of protecting mammals from acute renal ischemic-reperfusion injury and cold-induced kidney tubule damage.^[1]^[2] It is being studied for the treatment of obesity^[3] sepsis,^[1]^[4] and cancer.^[5]^[6]

References

^ ^a ^b Tsuji, Naoko; Tsuji, Takayuki; Yamashita, Tetsushi; Hayase, Naoki; Hu, Xuzhen; Yuen, Peter S. T.; Star, Robert A. (3 April 2023). "BAM15 treats mouse sepsis and kidney injury, linking mortality, mitochondrial DNA, tubule damage, and neutrophils". The Journal of Clinical Investigation. 133 (7). doi:10.1172/JCI152401. ISSN 0021-9738. PMC 10065071. PMID 36757801.
^ Alexopoulos, Stephanie J.; Chen, Sing-Young; Brandon, Amanda E.; Salamoun, Joseph M.; Byrne, Frances L.; Garcia, Christopher J.; Beretta, Martina; Olzomer, Ellen M.; Shah, Divya P.; Philp, Ashleigh M.; Hargett, Stefan R.; Lawrence, Robert T.; Lee, Brendan; Sligar, James; Carrive, Pascal; Tucker, Simon P.; Philp, Andrew; Lackner, Carolin; Turner, Nigel; Cooney, Gregory J.; Santos, Webster L.; Hoehn, Kyle L. (2020). "Mitochondrial uncoupler BAM15 reverses diet-induced obesity and insulin resistance in mice". Nature Communications. 11 (1): 2397. Bibcode:2020NatCo..11.2397A. doi:10.1038/s41467-020-16298-2. PMC 7224297. PMID 32409697.
^ Axelrod, Christopher L; King, William T; Davuluri, Gangarao; Noland, Robert C; Hall, Jacob; Hull, Michaela; Dantas, Wagner S; Zunica, Elizabeth RM; Alexopoulos, Stephanie J; Hoehn, Kyle L; Langohr, Ingeborg; Stadler, Krisztian; Doyle, Haylee; Schmidt, Eva; Nieuwoudt, Stephan; Fitzgerald, Kelly; Pergola, Kathryn; Fujioka, Hisashi; Mey, Jacob T; Fealy, Ciaran; Mulya, Anny; Beyl, Robbie; Hoppel, Charles L; Kirwan, John P (7 July 2020). "BAM15‐mediated mitochondrial uncoupling protects against obesity and improves glycemic control". EMBO Molecular Medicine. 12 (7): e12088. doi:10.15252/emmm.202012088. ISSN 1757-4676. PMC 7338798. PMID 32519812.
^ Dang, Cong Phi; Issara-Amphorn, Jiraphorn; Charoensappakit, Awirut; Udompornpitak, Kanyarat; Bhunyakarnjanarat, Thansita; Saisorn, Wilasinee; Sae-Khow, Kritsanawan; Leelahavanichkul, Asada (1 June 2021). "BAM15, a Mitochondrial Uncoupling Agent, Attenuates Inflammation in the LPS Injection Mouse Model: An Adjunctive Anti-Inflammation on Macrophages and Hepatocytes". Journal of Innate Immunity. 13 (6): 359–375. doi:10.1159/000516348. ISSN 1662-811X. PMC 8613553. PMID 34062536.
^ Gao, Zhen xing; Cui, Ze long; Zhou, Min ran; Fu, Yue; Liu, Fen; Zhang, Lu; Ma, Sai; Chen, Chun yan (1 April 2022). "The new mitochondrial uncoupler BAM15 induces ROS production for treatment of acute myeloid leukemia". Biochemical Pharmacology. 198: 114948. doi:10.1016/j.bcp.2022.114948. ISSN 0006-2952. PMID 35192847. S2CID 247002108.
^ Zunica, Elizabeth R. M.; Axelrod, Christopher L.; Cho, Eunhan; Spielmann, Guillaume; Davuluri, Gangarao; Alexopoulos, Stephanie J.; Beretta, Martina; Hoehn, Kyle L.; Dantas, Wagner S.; Stadler, Krisztian; King, William T.; Pergola, Kathryn; Irving, Brian A.; Langohr, Ingeborg M.; Yang, Shengping; Hoppel, Charles L.; Gilmore, L. Anne; Kirwan, John P. (9 October 2021). "Breast cancer growth and proliferation is suppressed by the mitochondrial targeted furazano[3,4-b]pyrazine BAM15". Cancer & Metabolism. 9 (1): 36. doi:10.1186/s40170-021-00274-5. ISSN 2049-3002. PMC 8502397. PMID 34627389.

External links

Fat-fighting molecule sees the body burn more fuel

[Tsuji-1] Tsuji, Naoko; Tsuji, Takayuki; Yamashita, Tetsushi; Hayase, Naoki; Hu, Xuzhen; Yuen, Peter S. T.; Star, Robert A. (3 April 2023). "BAM15 treats mouse sepsis and kidney injury, linking mortality, mitochondrial DNA, tubule damage, and neutrophils". The Journal of Clinical Investigation. 133 (7). doi:10.1172/JCI152401. ISSN 0021-9738. PMC 10065071. PMID 36757801.

[2] Alexopoulos, Stephanie J.; Chen, Sing-Young; Brandon, Amanda E.; Salamoun, Joseph M.; Byrne, Frances L.; Garcia, Christopher J.; Beretta, Martina; Olzomer, Ellen M.; Shah, Divya P.; Philp, Ashleigh M.; Hargett, Stefan R.; Lawrence, Robert T.; Lee, Brendan; Sligar, James; Carrive, Pascal; Tucker, Simon P.; Philp, Andrew; Lackner, Carolin; Turner, Nigel; Cooney, Gregory J.; Santos, Webster L.; Hoehn, Kyle L. (2020). "Mitochondrial uncoupler BAM15 reverses diet-induced obesity and insulin resistance in mice". Nature Communications. 11 (1): 2397. Bibcode:2020NatCo..11.2397A. doi:10.1038/s41467-020-16298-2. PMC 7224297. PMID 32409697.

[3] Axelrod, Christopher L; King, William T; Davuluri, Gangarao; Noland, Robert C; Hall, Jacob; Hull, Michaela; Dantas, Wagner S; Zunica, Elizabeth RM; Alexopoulos, Stephanie J; Hoehn, Kyle L; Langohr, Ingeborg; Stadler, Krisztian; Doyle, Haylee; Schmidt, Eva; Nieuwoudt, Stephan; Fitzgerald, Kelly; Pergola, Kathryn; Fujioka, Hisashi; Mey, Jacob T; Fealy, Ciaran; Mulya, Anny; Beyl, Robbie; Hoppel, Charles L; Kirwan, John P (7 July 2020). "BAM15‐mediated mitochondrial uncoupling protects against obesity and improves glycemic control". EMBO Molecular Medicine. 12 (7): e12088. doi:10.15252/emmm.202012088. ISSN 1757-4676. PMC 7338798. PMID 32519812.

[4] Dang, Cong Phi; Issara-Amphorn, Jiraphorn; Charoensappakit, Awirut; Udompornpitak, Kanyarat; Bhunyakarnjanarat, Thansita; Saisorn, Wilasinee; Sae-Khow, Kritsanawan; Leelahavanichkul, Asada (1 June 2021). "BAM15, a Mitochondrial Uncoupling Agent, Attenuates Inflammation in the LPS Injection Mouse Model: An Adjunctive Anti-Inflammation on Macrophages and Hepatocytes". Journal of Innate Immunity. 13 (6): 359–375. doi:10.1159/000516348. ISSN 1662-811X. PMC 8613553. PMID 34062536.

[5] Gao, Zhen xing; Cui, Ze long; Zhou, Min ran; Fu, Yue; Liu, Fen; Zhang, Lu; Ma, Sai; Chen, Chun yan (1 April 2022). "The new mitochondrial uncoupler BAM15 induces ROS production for treatment of acute myeloid leukemia". Biochemical Pharmacology. 198: 114948. doi:10.1016/j.bcp.2022.114948. ISSN 0006-2952. PMID 35192847. S2CID 247002108.

[6] Zunica, Elizabeth R. M.; Axelrod, Christopher L.; Cho, Eunhan; Spielmann, Guillaume; Davuluri, Gangarao; Alexopoulos, Stephanie J.; Beretta, Martina; Hoehn, Kyle L.; Dantas, Wagner S.; Stadler, Krisztian; King, William T.; Pergola, Kathryn; Irving, Brian A.; Langohr, Ingeborg M.; Yang, Shengping; Hoppel, Charles L.; Gilmore, L. Anne; Kirwan, John P. (9 October 2021). "Breast cancer growth and proliferation is suppressed by the mitochondrial targeted furazano[3,4-b]pyrazine BAM15". Cancer & Metabolism. 9 (1): 36. doi:10.1186/s40170-021-00274-5. ISSN 2049-3002. PMC 8502397. PMID 34627389.

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