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X-ray structures of two xanthine inhibitors bound to PEPCK and N-3 modifications of substituted 1,8-dibenzylxanthines.

Foley LH, Wang P, Dunten P, Ramsey G, Gubler ML, Wertheimer SJ
Bioorg Med Chem Lett 13 3871-4 (2003)
Cited: 7 times
EuropePMC logo PMID: 14552798

Abstract

The analysis of the X-ray structures of two xanthine inhibitors bound to PEPCK and a comparison to the X-ray structure of GTP bound to PEPCK are reported. The SAR at N-1, N-7 and developing SAR at C-8 are consistent with information gained from the X-ray structures of compounds 1 and 2 bound to PEPCK. Representative N-3 modifications of compound 2 that led to the discovery of 3-cyclopropylmethyl and its carboxy analogue as optimal N-3 groups are presented.

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Articles citing this publication (5)

  1. Inhibition of phosphoenolpyruvate carboxykinase blocks lactate utilization and impairs tumor growth in colorectal cancer. Montal ED, Bhalla K, Dewi RE, Ruiz CF, Haley JA, Ropell AE, Gordon C, Haley JD, Girnun GD. Cancer Metab 7 8 (2019)
  2. Modified 3-alkyl-1,8-dibenzylxanthines as GTP-competitive inhibitors of phosphoenolpyruvate carboxykinase. Foley LH, Wang P, Dunten P, Ramsey G, Gubler ML, Wertheimer SJ. Bioorg Med Chem Lett 13 3607-3610 (2003)
  3. Saccharomyces cerevisiae phosphoenolpyruvate carboxykinase: relevance of arginine 70 for catalysis. Cristina Ravanal M, Flores M, Pérez E, Aroca F, Cardemil E. Biochimie 86 357-362 (2004)
  4. C-8 Modifications of 3-alkyl-1,8-dibenzylxanthines as inhibitors of human cytosolic phosphoenolpyruvate carboxykinase. Pietranico SL, Foley LH, Huby N, Yun W, Dunten P, Vermeulen J, Wang P, Toth K, Ramsey G, Gubler ML, Wertheimer SJ. Bioorg Med Chem Lett 17 3835-3839 (2007)
  5. Saccharomyces cerevisiae phosphoenolpyruvate carboxykinase: the relevance of Glu299 and Leu460 for nucleotide binding. Pérez E, Cardemil E. Protein J 29 299-305 (2010)


Related citations provided by authors (1)

  1. CRYSTAL STRUCTURE OF HUMAN CYTOSOLIC PHOSPHOENOLPYRUVATE CARBOXYKINASE REVEALS A NEW GTP-BINDING SITE. DUNTEN P, BELUNIS C, CROWTHER R, HOLLFELDER K, KAMMLOTT U, LEVIN W, MICHEL H, RAMSEY GB, SWAIN A, WEBER D, WERTHEIMER SJ J. Mol. Biol. 316 257-264 (2002)

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