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3-(2-carboxyethyl)-4,6-dichloro-1H-indole-2-carboxylic acid: an allosteric inhibitor of fructose-1,6-bisphosphatase at the AMP site.

Wright SW, Carlo AA, Danley DE, Hageman DL, Karam GA, Mansour MN, McClure LD, Pandit J, Schulte GK, Treadway JL, Wang IK, Bauer PH
Bioorg Med Chem Lett 13 2055-8 (2003)
Cited: 22 times
EuropePMC logo PMID: 12781194

Abstract

3-(2-Carboxyethyl)-4,6-dichloro-1H-indole-2-carboxylic acid (MDL-29951), an antagonist of the glycine site of the NMDA receptor, has been found to be an allosteric inhibitor of the enzyme fructose 1,6-bisphosphatase. The compound binds at the AMP regulatory site by X-ray crystallography. This represents a new approach to inhibition of fructose 1,6-bisphosphatase and serves as a lead for further drug design.

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  1. MB06322 (CS-917): A potent and selective inhibitor of fructose 1,6-bisphosphatase for controlling gluconeogenesis in type 2 diabetes. Erion MD, van Poelje PD, Dang Q, Kasibhatla SR, Potter SC, Reddy MR, Reddy KR, Jiang T, Lipscomb WN. Proc Natl Acad Sci U S A 102 7970-7975 (2005)
  2. Hypoglycemic effects of Ganoderma lucidum polysaccharides in type 2 diabetic mice. Xiao C, Wu QP, Cai W, Tan JB, Yang XB, Zhang JM. Arch Pharm Res 35 1793-1801 (2012)
  3. Benzoxazole benzenesulfonamides are novel allosteric inhibitors of fructose-1,6-bisphosphatase with a distinct binding mode. von Geldern TW, Lai C, Gum RJ, Daly M, Sun C, Fry EH, Abad-Zapatero C. Bioorg Med Chem Lett 16 1811-1815 (2006)
  4. 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)
  5. 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)
  6. Rational design, synthesis, and potency of N-substituted indoles, pyrroles, and triarylpyrazoles as potential fructose 1,6-bisphosphatase inhibitors. Rudnitskaya A, Borkin DA, Huynh K, Török B, Stieglitz K. ChemMedChem 5 384-389 (2010)
  7. Modeling the metabolic interplay between a parasitic worm and its bacterial endosymbiont allows the identification of novel drug targets. Curran DM, Grote A, Nursimulu N, Geber A, Voronin D, Jones DR, Ghedin E, Parkinson J. Elife 9 e51850 (2020)
  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. In silico identification of structure requirement for novel thiazole and oxazole derivatives as potent fructose 1,6-bisphosphatase inhibitors. Hao M, Zhang X, Ren H, Li Y, Zhang S, Luo F, Ji M, Li G, Yang L. Int J Mol Sci 12 8161-8180 (2011)
  10. 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)
  11. Discovery of novel indole derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase. Bie J, Liu S, Li Z, Mu Y, Xu B, Shen Z. Eur J Med Chem 90 394-405 (2015)
  12. 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)
  13. Structures of Leishmania Fructose-1,6-Bisphosphatase Reveal Species-Specific Differences in the Mechanism of Allosteric Inhibition. Yuan M, Vásquez-Valdivieso MG, McNae IW, Michels PAM, Fothergill-Gilmore LA, Walkinshaw MD. J Mol Biol 429 3075-3089 (2017)
  14. Toward the prediction of FBPase inhibitory activity using chemoinformatic methods. Hao M, Zhang S, Qiu J. Int J Mol Sci 13 7015-7037 (2012)
  15. 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)
  16. Exploration of N-Arylsulfonyl-indole-2-carboxamide Derivatives as Novel Fructose-1,6-bisphosphatase Inhibitors by Molecular Simulation. Zhao Y, Yang H, Wu F, Luo X, Sun Q, Feng W, Ju X, Liu G. Int J Mol Sci 23 10259 (2022)
  17. 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)
  18. Straightforward synthesis of N-arylindoles via one-pot Fischer indolisation-indole N-arylation. Lintott M, Perry A. RSC Adv 13 15993-15997 (2023)


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