SB-431542

SB-431542
Names
	Preferred IUPAC name 4-[4-(2H-1,3-Benzodioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl]benzamide
Identifiers
CAS Number	301836-41-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:91108 ;
ChEMBL	ChEMBL440084;
ChemSpider	3716512;
IUPHAR/BPS	8216;
PubChem CID	4521392;
UNII	E1557V1V0N;
CompTox Dashboard (EPA)	DTXSID7042693 ;
	InChI InChI=1S/C22H16N4O3/c23-21(27)13-4-6-14(7-5-13)22-25-19(20(26-22)16-3-1-2-10-24-16)15-8-9-17-18(11-15)29-12-28-17/h1-11H,12H2,(H2,23,27)(H,25,26) Key: FHYUGAJXYORMHI-UHFFFAOYSA-N; InChI=1/C22H16N4O3/c23-21(27)13-4-6-14(7-5-13)22-25-19(20(26-22)16-3-1-2-10-24-16)15-8-9-17-18(11-15)29-12-28-17/h1-11H,12H2,(H2,23,27)(H,25,26) Key: FHYUGAJXYORMHI-UHFFFAOYAN;
	SMILES NC(=O)c1ccc(cc1)c2nc(c3ccc4OCOc4c3)c([nH]2)c5ccccn5;
Properties
Chemical formula	C22H16N4O3
Molar mass	384.395 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

SB-431542 is a drug candidate developed by GlaxoSmithKline (GSK) as an inhibitor of the activin receptor-like kinase (ALK) receptors, ALK5, ALK4 and ALK7.[1] However, it is not an inhibitor of anaplastic lymphoma kinase (which are commonly known as ALK inhibitors).

In-vitro studies

While SB-431542 has not proved directly useful for any clinical application, it is used for several applications in molecular biology. It suppresses the TGF-beta-induced proliferation of osteosarcoma cells in humans.[1] Treatment with SB431542 is a robust, clinically applicable, and efficient system for generating mesenchymal stem/stromal cells (MSCs) from human iPSCs.[2] SB431542 can also be used in combination with LDN193189, CHIR99021 and DAPT to transform astrocytes into neurons.[3] It is also commonly used for immunological studies, for instance as a TGF-β inhibitor to facilitate the generation of dendritic cells from peripheral blood monocytes. [4]

References

Laping, NJ; Grygielko E; Mathur A; Butter S; Bomberger J; Tweed C; Martin W; Fornwald J; Lehr R; Harling J; Gaster L; Callahan JF; Olson BA (2002). "Inhibition of transforming growth factor (TGF)-beta1-induced extracellular matrix with a novel inhibitor of the TGF-beta type I receptor kinase activity: SB-431542". Molecular Pharmacology. 62 (1): 58–64. doi:10.1124/mol.62.1.58. PMID 12065755.
Chen, Yen Shun; Pelekanos, Rebecca A.; Ellis, Rebecca L.; Horne, Rachel; Wolvetang, Ernst J.; Fisk, Nicholas M. (2012). "Small Molecule Mesengenic Induction of Human Induced Pluripotent Stem Cells to Generate Mesenchymal Stem/Stromal Cells". Stem Cells Translational Medicine. 1 (2): 83–95. doi:10.5966/sctm.2011-0022. PMC 3659681. PMID 23197756.
Yin, Jiu-Chao; Zhang, Lei; Ma, Ning-Xin; Wang, Yue; Lee, Grace; Hou, Xiao-Yi; Lei, Zhuo-Fan; Zhang, Feng-Yu; Dong, Feng-Ping; Wu, Gang-Yi; Chen, Gong (2019). "Chemical Conversion of Human Fetal Astrocytes into Neurons through Modulation of Multiple Signaling Pathways". Stem Cell Reports. 12 (3): 488–501. doi:10.1016/j.stemcr.2019.01.003. PMC 6409415. PMID 30745031.
Mondanelli G; Bianchi R; Pallotta MT; Orabona C; Albini E; Iacono A; Belladonna ML; Vacca C; Fallarino F; Macchiarulo A; Ugel S; Bronte V; Gevi F; Zolla L; Verhaar A; Peppelenbosch M; Mazza EMC; Bicciato S; Laouar Y; Santambrogio L; Puccetti P; Volpi C; Grohmann U (2017). "A Relay Pathway between Arginine and Tryptophan Metabolism Confers Immunosuppressive Properties on Dendritic Cells". Immunity. 42 (2). doi:10.1016/j.immuni.2017.01.005. PMC 5337620. PMID 30745031.

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[Grygielko2002-1] Laping, NJ; Grygielko E; Mathur A; Butter S; Bomberger J; Tweed C; Martin W; Fornwald J; Lehr R; Harling J; Gaster L; Callahan JF; Olson BA (2002). "Inhibition of transforming growth factor (TGF)-beta1-induced extracellular matrix with a novel inhibitor of the TGF-beta type I receptor kinase activity: SB-431542". Molecular Pharmacology. 62 (1): 58–64. doi:10.1124/mol.62.1.58. PMID 12065755.

[2] Chen, Yen Shun; Pelekanos, Rebecca A.; Ellis, Rebecca L.; Horne, Rachel; Wolvetang, Ernst J.; Fisk, Nicholas M. (2012). "Small Molecule Mesengenic Induction of Human Induced Pluripotent Stem Cells to Generate Mesenchymal Stem/Stromal Cells". Stem Cells Translational Medicine. 1 (2): 83–95. doi:10.5966/sctm.2011-0022. PMC 3659681. PMID 23197756.

[3] Yin, Jiu-Chao; Zhang, Lei; Ma, Ning-Xin; Wang, Yue; Lee, Grace; Hou, Xiao-Yi; Lei, Zhuo-Fan; Zhang, Feng-Yu; Dong, Feng-Ping; Wu, Gang-Yi; Chen, Gong (2019). "Chemical Conversion of Human Fetal Astrocytes into Neurons through Modulation of Multiple Signaling Pathways". Stem Cell Reports. 12 (3): 488–501. doi:10.1016/j.stemcr.2019.01.003. PMC 6409415. PMID 30745031.

[4] Mondanelli G; Bianchi R; Pallotta MT; Orabona C; Albini E; Iacono A; Belladonna ML; Vacca C; Fallarino F; Macchiarulo A; Ugel S; Bronte V; Gevi F; Zolla L; Verhaar A; Peppelenbosch M; Mazza EMC; Bicciato S; Laouar Y; Santambrogio L; Puccetti P; Volpi C; Grohmann U (2017). "A Relay Pathway between Arginine and Tryptophan Metabolism Confers Immunosuppressive Properties on Dendritic Cells". Immunity. 42 (2). doi:10.1016/j.immuni.2017.01.005. PMC 5337620. PMID 30745031.