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Allosteric FBPase inhibitors gain 10(5) times in potency when simultaneously binding two neighboring AMP sites.

Hebeisen P, Kuhn B, Kohler P, Gubler M, Huber W, Kitas E, Schott B, Benz J, Joseph C, Ruf A
Bioorg Med Chem Lett 18 4708-12 (2008)
Cited: 24 times
EuropePMC logo PMID: 18650089

Abstract

Human fructose-1,6-bisphosphatase (FBPase, EC 3.1.3.11) is a key gluconeogenic enzyme, responsible for the hydrolysis of fructose-1,6-bisphosphate to fructose-6-phosphate, and thus presents an opportunity for the development of novel therapeutics focused on lowering the hepatic glucose production in type 2 diabetics. In its active form FBPase exists as a homotetramer and is allosterically regulated by AMP. In an HTS campaign aromatic sulfonylureas have been identified as FBPase inhibitors mimicking AMP. By bridging two adjacent allosteric binding sites using two aromatic sulfonylureas as anchor units and covalently linking them, it was possible to obtain dual binding AMP site inhibitors that exhibit a strong inhibitory effect.

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  1. Structure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors. Tsukada T, Takahashi M, Takemoto T, Kanno O, Yamane T, Kawamura S, Nishi T. Bioorg. Med. Chem. Lett. 20 1004-1007 (2010)
  2. Synthesis, SAR, and X-ray structure of tricyclic compounds as potent FBPase inhibitors. Tsukada T, Takahashi M, Takemoto T, Kanno O, Yamane T, Kawamura S, Nishi T. Bioorg. Med. Chem. Lett. 19 5909-5912 (2009)
  3. Sulfonylureido thiazoles as fructose-1,6-bisphosphatase inhibitors for the treatment of type-2 diabetes. Kitas E, Mohr P, Kuhn B, Hebeisen P, Wessel HP, Haap W, Ruf A, Benz J, Joseph C, Huber W, Sanchez RA, Paehler A, Benardeau A, Gubler M, Schott B, Tozzo E. Bioorg. Med. Chem. Lett. 20 594-599 (2010)
  4. 3D-QSAR studies and molecular docking on [5-(4-amino-1H-benzoimidazol-2-yl)-furan-2-yl]-phosphonic acid derivatives as fructose-1,6-biphophatase inhibitors. Lan P, Xie MQ, Yao YM, Chen WN, Chen WM. J. Comput. Aided Mol. Des. 24 993-1008 (2010)
  5. Discovery of Potent, Selective, and Structurally Novel Dot1L Inhibitors by a Fragment Linking Approach. Möbitz H, Machauer R, Holzer P, Vaupel A, Stauffer F, Ragot C, Caravatti G, Scheufler C, Fernandez C, Hommel U, Tiedt R, Beyer KS, Chen C, Zhu H, Gaul C. ACS Med Chem Lett 8 338-343 (2017)
  6. Elucidation of direct competition and allosteric modulation of small-molecular-weight protein ligands using surface plasmon resonance methods. Huber W, Sinopoli A, Kohler J, Hug M, Ruf A, Huber S. J. Mol. Recognit. 28 480-491 (2015)
  7. Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase. Hebeisen P, Haap W, Kuhn B, Mohr P, Wessel HP, Zutter U, Kirchner S, Ruf A, Benz J, Joseph C, Alvarez-Sánchez R, Gubler M, Schott B, Benardeau A, Tozzo E, Kitas E. Bioorg. Med. Chem. Lett. 21 3237-3242 (2011)
  8. Design, synthesis and biological evaluation of 7-nitro-1H-indole-2-carboxylic acid derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase. Bie J, Liu S, Zhou J, Xu B, Shen Z. Bioorg. Med. Chem. 22 1850-1862 (2014)
  9. Molecular modeling studies on phosphonic acid-containing thiazole derivatives: design for fructose-1,6-bisphosphatase inhibitors. Lan P, Wu ZW, Chen WN, Sun PH, Chen WM. J Mol Model 18 973-990 (2012)
  10. Small-Molecule Activators of Glucose-6-phosphate Dehydrogenase (G6PD) Bridging the Dimer Interface. Raub AG, Hwang S, Horikoshi N, Cunningham AD, Rahighi S, Wakatsuki S, Mochly-Rosen D. ChemMedChem 14 1321-1324 (2019)
  11. Synthesis and structure-activity relationship of non-phosphorus-based fructose-1,6-bisphosphatase inhibitors: 2,5-Diphenyl-1,3,4-oxadiazoles. Liao BR, He HB, Yang LL, Gao LX, Chang L, Tang J, Li JY, Li J, Yang F. Eur J Med Chem 83 15-25 (2014)
  12. Discovery of potent and orally active tricyclic-based FBPase inhibitors. Tsukada T, Kanno O, Yamane T, Tanaka J, Yoshida T, Okuno A, Shiiki T, Takahashi M, Nishi T. Bioorg. Med. Chem. 18 5346-5351 (2010)
  13. Quadruple space-group ambiguity owing to rotational and translational noncrystallographic symmetry in human liver fructose-1,6-bisphosphatase. Ruf A, Tetaz T, Schott B, Joseph C, Rudolph MG. Acta Crystallogr D Struct Biol 72 1212-1224 (2016)
  14. Correcting glucose-6-phosphate dehydrogenase deficiency with a small-molecule activator. Hwang S, Mruk K, Rahighi S, Raub AG, Chen CH, Dorn LE, Horikoshi N, Wakatsuki S, Chen JK, Mochly-Rosen D. Nat Commun 9 4045 (2018)
  15. Protein-based alignment in 3D-QSAR of FBPase inhibitors. Yi P, Di YT, Liu W, Hao XJ, Ming Y, Huang DS, Yang J, Yi ZZ, Li ZJ, Yang RD, Zhang JC. Eur J Med Chem 46 885-892 (2011)
  16. Pushing the Ligand Efficiency Metrics: Relative Group Contribution (RGC) Model as a Helpful Strategy to Promote a Fragment "Rescue" Effect. Vásquez AF, González Barrios A. Front Chem 7 564 (2019)


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