Biographical Sketch
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NAME |
POSITION TITLE Don Matteson Professor of Chemistry |
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EDUCATION/TRAINING (Begin with baccalaureate or other initial professional education, such as nursing, and include postdoctoral training.) |
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INSTITUTION AND LOCATION |
DEGREE |
YEAR(s) |
FIELD OF STUDY |
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University of Michigan, Ann Arbor, MI |
B.S. |
1982 |
Medicinal Chemistry |
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University of Washington, Seattle, WA |
Ph.D |
1987 |
Medicinal Chemistry |
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University of Wisconsin, Madison, WI |
Postdoctoral |
1988-90 |
Biochemistry |
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Professional Experience:
1987-88: Postdoctoral Fellow in the laboratory of Professor William Trager, Department of Medicinal Chemistry, University of Washington, Seattle, WA.
1988-89: Postdoctoral Fellow in the laboratory of Professor W. W. Cleland, Department of Biochemistry, University of Wisconsin, Madison, WI.
1990-95: Assistant Professor, Department of Pharmacology, University of Rochester, Rochester, NY.
1996-98: Associate Professor, Department of Pharmacology and Physiology, University of Rochester, Rochester, NY.
1996-98 Associate Professor of Biophysics, University of Rochester, Rochester, NY.
1998-02: Associate Professor, Department of Chemistry, Washington State University, Pullman, WA
2002-Pres: Professor, Department of Chemistry, Washington State University, Pullman, WA.
Other Experience:
1998-2003 Member of the Scientific Advisory Board for Camitro Corporation.
1998 Cofounder of Camitro Corporation with Ken Korzekwa and Camila Olsen.
2001 An expert panelist for the EPA QSAR workshop on risk assessment.
2001-2002 President of the WSU Faculty Association for Scholarship and Research.
2004-Present American Cancer Society Grant Reviewer
Grant reviewer for NCI, Special Emphasis Panels.
Grant Reviewer, Ad Hoc, XNDA study section
2003-Present Member of Drug Metabolism and Disposition Editorial Board
Publications: (selected publications)
Korzekwa KR, Jones JP, and Gillette JR. Theoretical studies on cytochrome P-450 mediated hydroxylation: A predictive model for hydrogen atom abstractions. J. Amer. Chem. Soc. 112: 7042-7046, 1990.
Jones JP, and Urbauer JL. Theoretical kinetic isotope effects for hydride transfer from formate to carbon dioxide: A comparison of theory with experiment. J. Comp. Chem. 12: 1134-1141, 1991.
Jones JP, Trager WF, and Carlson TJ. The binding and regioselectivity of reaction of (R) and (S)-nicotine with cytochrome P-450cam: Parallel experimental and theoretical studies. J. Amer. Chem. Soc. 115: 381-387, 1993.
Korzekwa KR, Jones JP. Predicting the cytochrome P450 mediated metabolism of xenobiotics. Pharmacogenetics 3: 1-18, 1993.
Dinnocenzo JP, Karki SB, and Jones JP. Isotope effects for the cytochrome P-450 oxidation of substituted N,N-dimethyl anilines. J. Amer. Chem. Soc. 115: 7111-7116, 1993.
Yin H, Bennett G, and Jones JP. Mechanistic studies of UDP-glucuronosyltransferase. Chemico-Biol. Interact. 90: 47-58, 1994.
Jones JP, Shou M, and Korzekwa KR. Stereospecific activation of the procarcinogen benzo[a]pyrene to probe the active site of the cytochrome P450 superfamily. Biochemistry, 34: 6956-6961,1995.
Dinnocenzo JP, Karki SB, Jones JP, and Korzekwa KR. The mechanism of oxidative amine dealkylation by cytochrome P450: Application of isotope effect profiles. J. Am. Chem. Soc., 117: 3657-3664, 1995.
Yin H, Anders MW, and Jones JP. Metabolism of 1,2-dichloro-1-fluoroethane and 1-fluoro-1,2,2-trichloroethane: Electronic factors govern the regioselectivity of cytochrome P450-dependent oxidation. Chem. Res. Toxicol. 9: 50-57, 1996.
Jones JP, He M, Trager WF, and Rettie AW. 3D-QSAR for inhibitors of cytochrome P450 2C9. Drug Metab. Dispos. 24: 1-6, 1996.
Jones JP, and Korzekwa KR. Predicting binding affinities and rates of reaction for the P450 superfamily. In: “Methods in Enzymology.” Ed. E. F. Johnson, and M. R. Waterman. Invited Chapter, Vol. 272b, pp. 326-335, 1997.
Manchester JI, Dinnocenzo JP, Higgins L and Jones JP. A new mechanistic probe for cytochrome P450. J. Am. Chem. Soc. 119: 5069-5070, 1997.
Iyer KR, Jones JP, Darbyshire JF, and Trager WF. Intramolecular isotope effects of benzylic hydroxylation of isomeric xylenes and 4,4’-dimethylbiphenyl by cytochrome P450: Relationship between distance of methyl groups and masking of the intrinsic isotope effect. Biochemistry 36: 7136-7143, 1997.
Higgins, L, Bennett, G. A., Shimoji, M. & Jones, J.P. Evaluation of Cytochrome P450 Mechanism and Kinetics Using Kinetic Deuterium Isotope Effects. Biochemistry, 37, 7036-7046, 1998.
Shimoji, M., Yin, H., Higgins, L. Jones, J.P. Design of a Novel P450: A Functional Bacterial/Human Cytochrome P450 Chimera. Biochemistry, 37, 8848-8852, 1998.
Goto, Y., Watanabe, Y., Fukuzumi, S., Jones, J. P. Dinnocenzo, J. P. Mechanisms of N-Demethylations Catalyzed by High-Valent Species of Heme Enzymes: Novel Use of Isotope Effects and Direct Observation of Intermediates. J. Amer. Chem. Soc. 120: 10762-10763, 1998.
Audergon, C., Iyer, K.R., Jones, J.P., Darbyshire, J.F, Trager, W.F. Experimental and theoretical approaches to study the active site topography of CYP101 (P450cam). J. Amer, Chem. Soc. 121, 41-47, 1999.
Haining, R.L., Jones, J.P., Henne, K., Fisher, M.B., Trager, W.F., Rettie, A.E. Phenylalanine 114 is a Critical, Substrate-Dependent Determinant of Specificity in Human Cytochrome P450 2C9. Biochemistry, 38, 3285-3292, 1999.
Koenigs, L.L., Jones, J.P., Friedberg, T., Pritchard, M. P., Shou, M., Rushmore, T.H., Trager, W. F. Mechanism-Based Inactivation of Cytochrome P450 3A4 by L-754,394. Biochemistry, 2000;39:4276-87.
Rao S, Aoyama R, Schrag M, Trager WF, Rettie A, Jones JP, A refined 3-dimensional QSAR of cytochrome P450 2C9: computational predictions of drug interactions.J Med Chem. 2000;43:2789-96.
Higgins, L., Korzekwa, K.R., Shou, M., Jones, J.P. A Method for the Assessment of Reaction Energetics for Cytochrome P450 Mediated Reactions. Archives of Biochemistry and Biophysics, 2001, 385, 220-230.
Ekins, S., de Groot, M.J., Jones, J.P. Pharmacophores and three Dimensional Quantitative Structure Activity Relationship Methods for Modeling Cytochrome P450 Active Sites. Drug Metabolism and Disposition, 2001, 29, 936-944.
Rock D, Rock D, Jones JP. Inexpensive purification of P450 reductase and other proteins using 2 ',5 '-adenosine diphosphate agarose affinity columns. Prot. Express. Pur. , 2001, 22: 82-83.
French, K. J., Strickler, M. D., Rock, D. A., Rock, D. A., Bennett, G. A., Wahlstrom, J. L. Goldstein, B. M., Jones, J. P. Benign Synthesis of 2-ethylhexanoic acid by Cytochrome P450cam: Enzymatic, Crystallographic, and Theoretical Studies. Biochemistry, 2001; 40; 9532-9538.
Kevin J. French, Dan A. Rock, Denise A. Rock, John I. Manchester, Barry M. Goldstein, and Jeffrey P. Jones* “Rational Design of Cytochrome P450cam: Understanding the structural basis for the oxidase shunt and improving the benign synthesis of 2-Ethylhexanoic Acid” Arch. Biochem. Biophysics.2002, 398, 188-97.
Jeffrey P. Jones*, Michael Mysinger, Kenneth Ray Korzekwa “Computational Models for Cytochrome P450: Predictive Electronic Model for Aromatic Oxidation and Hydrogen Atom abstraction” Drug Metab. Disp. 2002, 1, 7-12.
Dan A. Rock, Anthony E. Boitano, Jan L. Wahlstrom, Denise A. Rock, and Jeffrey P. Jones* “The Use of Kinetic Isotope Effects to Delineate the Role of Phenylalanine 87 in P450BM-3 “ Bioorganic Chemistry, 2002; 30, 107-118.
Volz, T., Rock, D.A., Jones, J.P.“Direct Evidence for Two Different Active Oxygen Species in Cytochrome P450BM3 Mediated Sulfoxidation and N-Dealkylkation Reactions.” Journal of the American Chemical Society, 2002, 124(33); 9724-9725.
Strickler M, Goldstein BM, Maxfield K, Shireman L, Kim G, Matteson DS, Jones JP. “ Crystallographic studies on the complex behavior of nicotine binding to P450cam (CYP101).” Biochemistry. 2003 Oct 21;42(41):11943-50.
Rock DA, Perkins BNS, Wahlstrom J, Jones JP. “A method for determining two substrates binding in the same active site of cytochrome P450(BM3): an explanation of high energy omega product formation.” Arch. Biochem. Biophysics. 416 (1): 9-16 AUG 1 2003.
Tornero-Velez R, Ross MK, Granville C, Laskey J, Jones JP, DeMarini DM,Evans MV “Metabolism and mutagenicity of source water contaminants 1,3-dichloropropane and 2,2-dichloropropane” Drug Metab. and Disp. 32 (1): 123-131 JAN 1 2004.
Dowers, T. S., Rock, D. A., Rock, D. A., Perkins, B. N. S., Jones, J. P. (2004). “An analysis of the regioselectivity of aromatic hydroxylation and N-oxygenation by cytochrome P450 enzymes.” Drug Metab. and Disp. 32 (3): 328-332.
Dickmann, L. J., Locuson, C. W., Jones, J. P. and Rettie. A.E., “Differential Roles of Arg97, Asp293, and Arg108 in Enzyme Stability and Substrate Specificity of CYP2C9.” Mol Pharmacol 65: 842-850, 2004.
Locuson,C.W. II, Rock, D.A., and Jones, J.P., “Quantitative Binding Models for CYP2C9 Based on Benzbromarone Analogues, Biochemistry, Web Release Date: 13-May-2004.
Dowers, T. S., D. A. Rock, D. A. Rock and J. P. Jones (2004). "Kinetic isotope effects implicate the iron-oxene as the sole oxidant in P450-catalyzed N-dealkylation." Journal of the American Chemical Society 126(29): 8868-8869.
Rettie, A., Jones, J.P. (2005) “Clinical and toxicological relevance of CYP2C9: Drug- drug interactions and pharmacogenetics” Annual Review of Pharmacology and Toxicology 45 477-494.
Hudelson MG, Jones JP. (2006) “Line-walking method for predicting the inhibition of p450 drug metabolism.” J Med Chem. 2006 Jul 13;49(14):4367-73.
Dowers TS, Jones JP (2006) “Kinetic isotope effects implicate a single oxidant for cytochrome P450-mediated O-dealkylation, N-oxygenation, and aromatic hydroxylation of 6-methoxyquinoline.” Drug Metab Dispos. 2006 Aug;34(8):1288-90.
Charles W. Locuson, Larry C. Wienkers, Jeffrey P. Jones, and Timothy S. Tracy (2007). "CYP2C9 Protein Interactions with Cytochrome b5: Effects on the Coupling of Catalysis." Drug Metabolism and Disposition., 35, 1174-1181.
Cho, K. Y., Y. Moreau, J.P. Jones and Shaik, S. (2007). ""Formation of the Active Species of Cytochrome P450 by Using Iodosylbenzene: A Case for Spin-Selective Reactivity"." Chemistry: A European Journal 13: 4103-5115.
Sheridan, R.P., Korzekwa, K.R. , Rhonda A. Torres, R.A., Walker, M. (2007). “Empirical Regioselectivity Models for Human Cytochromes P450 3A4, 2D6, and 2C9.” J Med Chem, 50, 3173-3184.
McMasters, D.R., Torres, R.A., Crathern, S.J., Dooney, D.L., Nachbar, R.B., Sheridan, R.P, Korzekwa, K.R. (2007). “Inhibition of Recombinant Cytochrome P450 Isoforms 2D6 and 2C9 by Diverse Drug-like Molecules” J Med Chem, 50, 3205-3213.
Torres, R.A., Korzekwa, K.R., McMasters, D.R., Fandozzi,I C.M., Jones, J.P. (2007). "On the Use of Density Functional Calculations to Predict the Regioselectivity of Drugs and Molecules Metabolized by Aldehyde Oxidase. J. Med. Chem, 50, 4642-4647.
Hudelson, M. G.; Ketkar, N. S.; Holder, L. B.; Carlson, T. J.; Peng, C.; Waldher, B. J.; Jones, J. P. (2008). "High Confidence Predictions of Drug−Drug Interactions: Predicting Affinities for Cytochrome P450 2C9 with Multiple Computational Methods." J. Med. Chem.; 2008 Feb 14;51(3):648-54. Epub 2008 Jan 19. DOI: 10.1021/jm701130z
Peng, C. C., Rushmore, T., Crouch, G. J., Jones, J. P. (2008). ” Modeling and Synthesis of Novel Tight-Binding Inhibitors of Cytochrome P450 2C9. Bioorganic and Medicinal Chemistry,” 2008 Apr 1;16(7):4064-74. Epub 2008 Jan18.
Peng, C. C., Rushmore, T., Crouch, G. J., Jones, J. P. (2008). “Cytochrome P450 2C9 Type II Binding Studies on Quinoline-4-Carboxamide Analogues” J. Med. Chem, 51 (24): 8000-8011.
Alfaro, J. F., Jones, J. P. (2008). ”Studies on the Mechanism of Aldehyde Oxidase and Xanthine Oxidase.” Journal of Organic Chemistry. 73 (23): 9469-9472.
Research Projects Ongoing During the Last 3 Years:
ACTIVE:
“Predicting Rates and Regioselectivity in Cytochrome P450 Mediated Reactions”
Principal Investigator: Jeffrey P. Jones
Agency: National Institutes of General Medical Sciences
Type of Award: 9R01 GM084546, 09/10/08-06/30/12
This is a continuation of the “Cytochrome P450 Models for Risk Assessment” grant.
COMPLETED:
“Cytochrome P450 Models for Risk Assessment”
Principal Investigator: Jeffrey P. Jones
Agency: National Institutes of Environmental Health
Type of Award: R01 ES09122, 5/1/03-4/31/08
The long term objective of this research proposal is to develop energy relationships for predictive models for the cytochrome P450 enzymes. The cytochrome P450 enzymes (P450s) are versatile catalysts that play an important role in both the detoxification and bioactivation of chemicals.
“Drug Interactions”
Principal Investigator: (Rettie)
Agency: National Institute of General Medicine
Type of Award: P01 GM32165 8/1/83-7/31/08
To explore drug interactions in P450-catalyzed reactions with a focus on mechanism and clinical aspects.