An enzyme-coupled continuous fluorescence assay for farnesyl diphosphate synthases

Analytical Biochemistry

Volumn 421, Issue 1, 2012, Pages 158-163

  Dozier, Jonathan K ^a   Distefano, Mark D ^a  

^a University of Minnesota   (United States)

Author keywords

Assay; Coupled assay; Diphosphate; Farnesyl diphosphate synthase; Fluorescence assay; Protein farnesyl transferase; Pyrophosphate

Indexed keywords

ASSAYS; BIOSYNTHESIS; CATALYSIS; ENZYME ACTIVITY; FLUORESCENCE; PEPTIDES;

CONTINUOUS FLUORESCENCE; DIPHOSPHATES; FARNESYL DIPHOSPHATE SYNTHASE; FLUORESCENCE ASSAY; FLUORESCENCE QUANTUM YIELD; PROTEIN FARNESYLTRANSFERASE; PYROPHOSPHATE; RADIOLABELED SUBSTRATES;

FREQUENCY DOMAIN ANALYSIS;

ENZYME INHIBITOR; FARNESYL DIPHOSPHATE; FARNESYL DIPHOSPHATE SYNTHASE INHIBITOR; GERANYLTRANSFERASE; PROTEIN FARNESYLTRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME COUPLED CONTINUOUS FLUORESCENCE ASSAY; ENZYME MECHANISM; ESCHERICHIA COLI; FLUORESCENCE ANALYSIS; IC 50; NONHUMAN; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 84855894199     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2011.10.038     Document Type: Article

References (27)

1. J.E. Dunford, A.A. Kwaasi, M.J. Rogers, B.L. Barnett, F.H. Ebetino, R.G.G. Russell, U. Oppermann, and K.L. Kavanagh Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase J. Med. Chem. 51 2008 2187 2195 (Pubitemid 351503274)
2. A.J. Wiemer, R.J. Hohl, and D.F. Wiemer The intermediate enzymes of isoprenoid metabolism as anticancer targets Anti-Cancer Agents Med. Chem. 9 2009 526 542
3. M.B. Martin, J.S. Grimley, J.C. Lewis, H.T. Heath, B.N. Bailey, H. Kendrick, V. Yardley, A. Caldera, R. Lira, J.A. Urbina, S.N.J. Moreno, R. Docampo, S.L. Croft, and E. Oldfield Bisphosphonates inhibit the growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: a potential route to chemotherapy J. Med. Chem. 44 2001 909 916 (Pubitemid 32861615)
4. S.B. Gabelli, J.S. McLellan, A. Montalvetti, E. Oldfield, R. Docampo, and L.M. Amzel Structure and mechanism of the farnesyl diphosphate synthase from Trypanosoma cruzi: implications for drug design Proteins 62 2006 80 88 (Pubitemid 43063006)
5. L. Li, G.-P. Chen, Y. Yang, Y. Ye, L. Yao, and S.-J. Hu Chronic inhibition of farnesyl pyrophosphate synthase attenuates cardiac hypertrophy and fibrosis in spontaneously hypertensive rats Biochem. Pharmacol. 79 2010 399 406
6. M. Notarnicola, C. Messa, A. Cavallini, M. Bifulco, M.F. Tecce, D. Eletto, A. Di Leo, S. Montemurro, C. Laezza, and M.G. Caruso Higher farnesyl diphosphate synthase activity in human colorectal cancer inhibition of cellular apoptosis Oncology 67 2004 351 358
7. J.W. De Schutter, S. Zaretsky, S. Welbourn, A. Pause, and Y.S. Tsantrizos Novel bisphosphonate inhibitors of the human farnesyl pyrophosphate synthase Bioorg. Med. Chem. Lett. 20 2010 5781 5786
8. J.A. Urbina, B. Moreno, S. Vierkotter, E. Oldfield, G. Payares, C. Sanoja, B.N. Bailey, W. Yan, D.A. Scott, S.N.J. Moreno, and R. Docampo Trypanosoma cruzi contains major pyrophosphate stores and its growth in vitro and in vivo is blocked by pyrophosphate analogs J. Biol. Chem. 274 1999 33609 33615 (Pubitemid 129511673)
9. W. Jahnke, J.-M. Rondeau, S. Cotesta, A. Marzinzik, X. Pellé, M. Geiser, A. Strauss, M. Götte, F. Bitsch, R. Hemmig, C. Henry, S. Lehmann, J.F. Glickman, T.P. Roddy, S.J. Stout, and J.R. Green Allosteric non-bisphosphonate FPPS inhibitors identified by fragment-based discovery Nat. Chem. Biol. 6 2010 660 666
10. J. Gao, X. Chu, Y. Qiu, L. Wu, Y. Qiao, J. Wu, and D. Li Discovery of potent inhibitor for farnesyl pyrophosphate synthase in the mevalonate pathway Chem. Commun. 46 2010 5340 5342
11. A. Leon, L. Liu, Y. Yang, M.P. Hudock, P. Hall, F. Yin, D. Studer, K.-J. Puan, C.T. Morita, and E. Oldfield Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin J. Med. Chem. 49 2006 7331 7341 (Pubitemid 44913394)
12. M.R. Webb A continuous spectrophotometric assay for inorganic phosphate and for measuring phosphate release kinetics in biological systems Proc. Natl. Acad. Sci. USA 89 1992 4884 4887
13. C.E. Rieger, J. Lee, and J.L. Turnbull A continuous spectrophotometric assay for aspartate transcarbamylase and ATPases Anal. Biochem. 246 1997 86 95 (Pubitemid 27100511)
14. T. Scott Reid, K.L. Terry, P.J. Casey, and L.S. Beese Crystallographic analysis of CaaX prenyltransferases complexed with substrates defines rules of protein substrate selectivity J. Mol. Biol. 343 2004 417 433 (Pubitemid 39296875)
15. M. Sinensky Recent advances in the study of prenylated proteins BBA-Mol. Cell. Biol. L 1484 2000 93 106 (Pubitemid 30175960)
16. M. Crul, G.J. de Klerk, J.H. Beijnen, and J.H. Schellens Ras biochemistry and farnesyl transferase inhibitors: a literature survey Anti-Cancer Drugs 12 2001 163 184 (Pubitemid 32269912)
17. D.L. Pompliano, R.P. Gomez, and N.J. Anthony Intramolecular fluorescence enhancement: a continuous assay of Ras farnesyl:protein transferase J. Am. Chem. Soc. 114 1992 7945 7946
18. A.J. Krzysiak, D.S. Rawat, S.A. Scott, J.E. Pais, M. Handley, M.L. Harrison, C.A. Fierke, and R.A. Gibbs Combinatorial modulation of protein prenylation ACS Chem. Biol. 2 2007 385 389 (Pubitemid 350001560)
19. A.J. DeGraw, M.J. Keiser, J.D. Ochocki, B.K. Shoichet, and M.D. Distefano Prediction and evaluation of protein farnesyltransferase inhibition by commercial drugs J. Med. Chem. 53 2010 2464 2471
20. G. Hooff, D. Volmer, W. Wood, W. Müller, and G. Eckert Isoprenoid quantitation in human brain tissue: a validated HPLC-fluorescence detection method for endogenous farnesyl- (FPP) and geranylgeranylpyrophosphate (GGPP) Anal. Bioanal. Chem. 392 2008 673 680
21. H. Tong, A.J. Wiemer, J.D. Neighbors, and R.J. Hohl Quantitative determination of farnesyl and geranylgeranyl diphosphate levels in mammalian tissue Anal. Biochem. 378 2008 138 143
22. P.C. Lee, R. Petri, B.N. Mijts, K.T. Watts, and C. Schmidt-Dannert Directed evolution of Escherichia coli farnesyl diphosphate synthase (IspA) reveals novel structural determinants of chain length specificity Metab. Eng. 7 2005 18 26 (Pubitemid 40249904)
23. A.J. DeGraw, M.A. Hast, J. Xu, D. Mullen, L.S. Beese, G. Barany, and M.D. Distefano Caged protein prenyltransferase substrates: tools for understanding protein prenylation Chem. Biol. Drug Des. 72 2008 171 181
24. I. Gaon, T.C. Turek, V.A. Weller, R.L. Edelstein, S.K. Singh, and M.D. Distefano Photoactive analogs of farnesyl pyrophosphate containing benzoylbenzoate esters: synthesis and application to photoaffinity labeling of yeast protein farnesyltransferase J. Org. Chem. 61 1996 7738 7745 (Pubitemid 26381298)
25. B. Ku, J.-C. Jeong, B.N. Mijts, C. Schmidt-Dannert, and J.S. Dordick Preparation, characterization, and optimization of an in vitro C30 carotenoid pathway Appl. Environ. Microbiol. 71 2005 6578 6583 (Pubitemid 43194139)
26. K.L. Kavanagh, K. Guo, J.E. Dunford, X. Wu, S. Knapp, F.H. Ebetino, M.J. Rogers, R.G.G. Russell, and U. Oppermann The molecular mechanism of nitrogen-containing bisphosphonates as antiosteoporosis drugs Proc. Natl. Acad. Sci. USA 103 2006 7829 7834
27. Molecular Probes. EnzChek pyrophosphate assay kit (E-6645). http://probes.invitrogen.com/media/pis/mp06645.pdf (accessed September 30, 2011).