Structural basis for the inhibition of human 5,10-methenyltetrahydrofolate synthetase by N10-substituted folate analogues

Cancer Research

Volumn 69, Issue 18, 2009, Pages 7294-7301

  Wu, Dong ^a   Li, Yang ^a   Song, Gaojie ^a   Cheng, Chongyun ^a   Zhang, Rongguang ^b   Joachimiak, Andrzej ^b   Shaw, Neil ^a   Liu, Zhi Jie ^a  

^a INSTITUTE OF BIOPHYSICS   (China)

^b ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,10 METHENYLTETRAHYDROFOLATE SYNTHETASE INHIBITOR; ADENOSINE DIPHOSPHATE; ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; FOLIC ACID DERIVATIVE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME SUBSTRATE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ADENOSINE TRIPHOSPHATE; CARBON-NITROGEN LIGASES; CATALYTIC DOMAIN; ENZYME INHIBITORS; FOLIC ACID; HUMANS; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 70349754437     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-09-1927     Document Type: Article

References (37)

1. Appling DR. Compartmentation of folate-mediated one-carbon metabolism in eukaryotes. FASEB J 1991;5:2645-2651
2. Fox JT, Stover PJ. Folate-mediated one-carbon metabolism. Vitam Horm 2008;79:1-44.
3. Farber S, Diamond LK, Mercer RD, Sylvester RF, Wolff VA. Temporary remission in acute leukemia in children produced by folic acid antagonist, 4-aminopteroyl glutamic acid (aminopterin). N Engl J Med 1948;238:787-793
4. Chattopadhyay S, Moran RG, Goldman DI. Pemetrexed: biochemical and cellular pharmacology, mechanisms, and clinical applications. Mol Cancer Ther 2007;6:404-417 (Pubitemid 46332443)
5. Pui CH, Evans WE. Treatment of acute lymphoblastic leukemia. N Engl J Med 2006;354:166-178
6. Longley DB, Harkin DP, Johnston PG. 5-Fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer 2003;3:330-338 (Pubitemid 37328853)
7. Carreras CW, Santi DV. The catalytic mechanism and structure of thymidylate synthase. Annu Rev Biochem 1995;64:721-762
8. Sirotnak FM, Wendel HG, Bornmann WG, et al. Co-administration of probenecid, an inhibitor of a cMOAT/MRP-like plasma membrane ATPase, greatly enhanced the efficacy of a new 10-deazaaminopterin against human solid tumors in vivo . Clin Cancer Res 2000;6:3705-3712
9. Bertino JR. "Rescue" techniques in cancer chemotherapy: use of leucovorin and other rescue agents after methotrexate treatment. Semin Oncol 1977;4:203-216
10. Renwick SB, Snell K, Baumann U. The crystal structure of human cytosolic serine hydroxymethyltransferase: a target for cancer chemotherapy. Structure 1998;6:1105-1116 (Pubitemid 28434114)
11. Schirch V, Szebenyi DM. Serine hydroxymethyltransferase revisited. Curr Opin Chem Biol 2005;9:482-487
12. Stover P, Schirch V. Serine hydroxymethyltransferase catalyzes the hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate. J Biol Chem 1990;265:14227-14233 (Pubitemid 20281794)
13. Allegra CJ, Drake JC, Jolivet J, Chabner BA. Inhibition of phosphoribosylaminoimidazolecarboxamide transformylase by methotrexate and dihydrofolic acid polyglutamates. Proc Natl Acad Sci U S A 1985;82:4881-4885 (Pubitemid 15249910)
14. Piper JR, McCaleb GS, Montgomery JA, et al. Synthesis and antifolate activity of 5-methyl-5,10-dideaza analogues of aminopterin and folic acid and an alternative synthesis of 5,10-dideazatetrahydrofolic acid, a potent inhibitor of glycinamide ribonucleotide formyltransferase. J Med Chem 1988;31:2164-2169
15. Jolivet J. Human 5,10-methenyltetrahydrofolate synthetase. Methods Enzymol 1997;281:162-170
16. Huennekens FM, Henderson GB, Vitols KS, Grimshaw CE. Enzymatic activation of 5-formyltetrahydrofolate via conversion to 5, 10-methenyltetrahydrofolate. Adv Enzyme Regul 1984;22:3-13.
17. Jolivet J, Dayan A, Beauchemin M, Chahla D, Mamo A, Bertrand R. Biochemical and molecular studies of human methenyltetrahydrofolate synthetase. Oncologist 1996;1:248-253 (Pubitemid 26042859)
18. Maras B, Stover P, Valiante S, Barra D, Schirch V. Primary structure and tetrahydropteroylglutamate binding site of rabbit liver cytosolic 5,10-methenyltetrahydrofolate synthetase. J Biol Chem 1994;269:18429-18433 (Pubitemid 24224074)
19. Huang T, Schirch V. Mechanism for the coupling of ATP hydrolysis to the conversion of 5-formyltetrahydrofolate to 5,10-methenyltetrahydrofolate. J Biol Chem 1995;270:22296-22300
20. Chen S, Yakunin AF, Proudfoot M, Kim R, Kim SH. Structural and functional characterization of a 5,10-methenyltetrahydrofolate synthetase from Mycoplasma pneumoniae (GI: 13508087). Proteins 2005;61:433-443 (Pubitemid 41429149)
21. Meier C, Carter LG, Winter G, Owens RJ, Stuart DI, Esnouf RM. Structure of 5-formyltetrahydrofolate cycloligase from Bacillus anthracis (BA4489). Acta Crystallogr Sect F Struct Biol Cryst Commun 2007;63:168-172 (Pubitemid 46438676)
22. Field MS, Szebenyi DM, Stover PJ. Regulation of de novo purine biosynthesis by methenyltetrahydrofolate synthetase in neuroblastoma. J Biol Chem 2006;281:4215-4221
23. Field MS, Szebenyi DM, Perry CA, and Stover PJ. Inhibition of 5,10-methenyltetrahydrofolate synthetase. Arch Biochem Biophys 2007;458:194-201.
24. Berman HM, Bhat TN, Bourne PE, et al. The Protein Data Bank and the challenge of structural genomics. Nat Struct Biol 2000;7:957-959 (Pubitemid 30823276)
25. Stols L, Gu M, Dieckman L, Raffen R, Collart FR, Donnelly MI. A new vector for high-throughput, ligation-independent cloning encoding a tobacco etch virus protease cleavage site. Protein Expr Purif 2002;25:8-15. (Pubitemid 36034995)
26. Otwinowski Z, Minor W. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol 1997;276:307-326 (Pubitemid 27085611)
27. Long F, Vagin A, Young P, Murshudov GN. BALBES: a molecular-replacement pipeline. Acta Crystallogr D Biol Crystallogr 2008;64:125-132
28. McCoy AJ, Grosse-Kunstleve RW, Adams PD, Winn MD, Storoni LC, Read RJ. Phaser crystallographic software. J Appl Cryst 2007;40:658-674
29. Adams PD, Grosse-Kunstleve RW, Hung LW, et al. PHENIX: building new software for automated crystallographic structure determination. Acta Crystallogr D Biol Crystallogr 2002;58:1948-1954
30. Murshudov GN, Vagin AA, Dodson EJ. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D Biol Crystallogr 1997;53:240-255
31. Brünger AT. Free Rvalue : a novel statistical quantity for assessing the accuracy of crystal structures. Nature 1992;355:472-475
32. Emsley P, Cowtan K. Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr 2004;60:2126-2132 (Pubitemid 41742764)
33. Davis IW, Murray LW, Richardson JS, Richardson DC. MOLPROBITY: structure validation and all-atom contact analysis for nucleic acids and their complexes. Nucleic Acids Res 2004;32:615-619
34. May M, Bardos TJ, Barger FL, et al. Synthetic and degradative investigations of the structure of folinic acid-SF. J Am Chem Soc 1951;73:3067-3075
35. Girgis S, Suh JR, Jolivet J, Stover PJ. 5-Formyltetrahydrofolate regulates homocysteine remethylation in human neuroblastoma. J Biol Chem 1997;272:4729-4734 (Pubitemid 27090014)
36. Altschul SF, Madden TL, Schaøffer AA, et al. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res 1997;25:3389-3402
37. Larkin MA, Blackshields G, Brown NP, et al. Clustal W and Clustal X version 2.0. Bioinformatics 2007;23: 2947-2948