Methotrexate resistance of mouse dihydrofolate reductase: Effect of substitution of phenylalanine-31 by serine or tryptophan

Journal of Medicinal Chemistry

Volumn 39, Issue 9, 1996, Pages 1763-1766

  Evenson, David A ^a   Adams, Joseph ^b   McIvor, R Scott ^a   Wagner, Carston R ^c  

^a UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROFOLATE REDUCTASE; METHOTREXATE; PHENYLALANINE; SERINE; TRYPTOPHAN;

AMINO ACID SUBSTITUTION; ANTINEOPLASTIC ACTIVITY; DRUG PROTEIN BINDING; DRUG RESISTANCE; ENZYME KINETICS; ENZYME STRUCTURE; MOUSE; NONHUMAN; REVIEW; STEADY STATE;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; FOLIC ACID ANTAGONISTS; KINETICS; METHOTREXATE; MICE; MUTAGENESIS, SITE-DIRECTED; PHENYLALANINE; SERINE; TETRAHYDROFOLATE DEHYDROGENASE; THERMODYNAMICS; TRYPTOPHAN;

EID: 0029925573     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950793d     Document Type: Review

References (20)

1. Schweitzer, B. I.; Dicker, A. P.; Bertino, J. R. Dihydrofolate Reductase as a Therapeutic Target. FASEB J. 1990, 4, 2441-2452.
2. Chunduru, S. K.; Cody, V.; Luft, J. R.; Pangborn, W.; Appleman, J. R.; Blakley, R. L. Methotrexate-Resistant Variants of Human Dihydrofolate Reductase-Effects of Phe31 Substitutions. J. Biol. Chem. 1994, 269, 9547-9555.
3. Nakano, T.; Spencer, H. T.; Appleman, J. R.; Blakley, R. L. Critical Role of Phenylalanine-34 of Human Dihydrofolate Reductase in Substrate and Inhibitor Binding and in Catalysis. Biochemistry 1994, 33, 9945-9952.
4. Thillet, J.; Absil, J.; Stone, S. R.; Pictet, R. Site-Directed Mutagenesis of Mouse Dihydrofolate Reductase. Mutants with Increased Resistance to Methotrexate and Trimethoprim. J. Biol. Chem. 1988, 263, 12500-12508.
5. Wagner, C. R.; Thillet, J.; Benkovic, S. J. Complementary Perturbation of the Kinetic Mechanism and Catalytic Effectiveness of DHFR by Sidechain Interchange. Biochemistry 1992, 31, 7834-7840.
6. Morris, J. A.; McIvor, R. S. Saturation Mutagenesis at Dihydrofolate Reductase Codons 22 and 31 - A Variety of Amino Acid Substitutions Conferring Methotrexate Resistance. Biochem. Pharmacol. 1994, 47, 1207-1220.
7. McIvor, R. S.; Simonsen, C. C. Isolation and Characterization of a Variant Dihydrofolate Reductase cDNA From Methotrexate-Resistant Murine L5178Y cells. Nucleic Acids Res. 1990, 18, 7025-7032.
8. May, C.; Gunther, R.; McIvor, R. S. Protection of Mice From Lethal Doses of Methotrexate by Transplantation With Transgenic Marrow Expressing Drug-Resistant Dihydrofolate Reductase Activity. Blood 1995, 86, 2439-2448.
9. Kaufman, B. T. Methotrexate-Agarose in the Purification of Dihydrofolate Reductase. Methods Enzymol. 1974, 34, 272-281.
10. Huang, Z.; Wagner, C. R.; Benkovic, S. J. Nonadditivity of mutational effects at the folate binding site of Escherichia coli dihydrofolate reductase. Biochemistry 1994, 33, 11576-11585.
11. Thillet, J.; Adams, J. A.; Benkovic, S. J. The Kinetic Mechanism of Wild-Type and Mutant Mouse Dihydrofolate Reductases. Biochemistry 1990, 29, 5195-5202.
12. 18
13. Chang, A. C. Y.; Nunberg, J. H.; Kaufman, R. J.; Erlich, H. A.; Schimke, R. T.; Cohen, S. N. Phenotypic Expression in E. coli of a DNA Sequence Coding for Mouse Dihydrofolate Reductase Nature 1978, 275, 617-624.
14. Blakley, R. L. In Folates and Pterins; Blakley, R. L., Benkovic, S. J., Eds.; Wiley: New York, 1986; pp 191-273.
15. Stammers, D. K.; Champness, J. N.; Beddell, C. R.; Dann, J. G.; Eliopoulos, E.; Geddes, A. J.; Ogg, D.; North. A. C. T. The Structure of Mouse L1210 Dihydrofolate Reductase-Drug Complexes and the Construction of a Model of Human Enzyme. FEBS Lett. 1987, 218, 178-184.
16. Prendergast, N. J.; Appleman, J. R.; Delcamp, T. J.; Blakley, R. L.; Freisheim, J. H. Effects of Conversion of Phenylalanine-31 to Leucine on the Function of Human Dihydrofolate Reductase. Biochemistry 1989, 28, 4645-4650.
17. Oefner, C.; D'Arcy, A.; Winkler, F. K. Crystal Structure of Human Dihydrofolate Reductase Complexed With Folate. Eur. J. Biochem. 1988, 174, 377-385.
18. Stone, S. R.; Morrison, J. R. Mechanism of Inhibition of Dihydrofolate Reductases From Bacterial and Vertebrate Sources by Various Classes of Folate Analogs. Biochim. Biophys. Acta 1986, 869, 275-285.
19. Schweitzer, B. I.; Srimatkandada, S.; Gritsman, H.; Sheridan, R.; Venkataraghavan, R.; Bertino, J. R. Probing the Role of Two Hydrophobic Active Site Residues in the Human Dihydrofolate Reductase by Site-Directed Mutagenesis. J. Biol. Chem. 1989, 264, 20786-20795.
20. Stone, S. R.; Morrison, J. F. Kinetic mechanism of the reaction catalyzed by dihydrofolate reductase from Escherichia coli. Biochemistry 1982, 21, 3757-3765.