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FACULTY & STAFF

Cofactor-Dependent Oxidations and Oxygenations, and the Development of Suicide Inhibitors

• Chemical simulation of biogenesis of the 2,4,5-trihydroxyphenylalanine quinone (TPQ) cofactor of copper amine oxidases. Mechanistic distinctions point toward a unique role of the active site in the o-quinone water addition step, S Mandal, Y Lee, MM Purdy, and LM Sayre, J. Am. Chem. Soc., 122, 3574-3584 (2000).
• Novel tert-butyl migration in copper-mediated phenol o-oxygenation, S Mandal, D Macikenas, JD Protasiewicz, and LM Sayre, J. Org. Chem., 65, 4804-4809 (2000).
• Catalytic turnover of substrate benzylamines by the quinone-dependent plasma amine oxidase leads to H₂O₂-dependent inactivation. Evidence for generation of a cofactor-derived benzoxazole, Y Lee, E Shepard, J Smith, DM Dooley, and LM Sayre, Biochemistry, 40, 822-829 (2001).
• Temporary inactivation of plasma amine oxidase by alkylhydrazines. A combined enzyme/model study implicates cofactor reduction/reoxidation, but cofactor deoxygenation and subsequent reoxygenation in the case of hydrazine itself, Y Lee, H-B Jeon, H Huang, and LM Sayre, J. Org. Chem., 66, 1925-1937 (2001).
• Dicopper(II) complexes with flexible binucleating ligands containing two tridentate coordination sites”, CA VanOrman, KV Reddy, LM Sayre, and FL Urbach, Polyhedron, 20, 541-549 (2001).
• N¹,N¹⁰-Ethylene-bridged high-potential flavins: Synthesis, characterization, and reactivity, W-S Li, N Zhang, and LM Sayre, Tetrahedron, 57, 4507-4522 (2001).
• Reaction of amines with N¹,N¹⁰-ethylene-bridged high-potential flavins: The first NMR spectroscopic evidence of C^10a tetrahedral amine adducts, W-S Li and LM Sayre, Tetrahedron, 57, 4523-4536 (2001).
• Catalytic turnover of benzylamine by a model for the lysine tyrosylquinone (LTQ) cofactor of lysyl oxidase, KQ Ling, J Kim, and LM Sayre, J. Am. Chem. Soc., 123, 9606-9611 (2001).
• Towards the development of selective amine oxidase inhibitors.Mechanism-based inhibition of six copper containing amine oxidases, EM Shepard, J Smith, BO Elmore, JA Kuchar, LM Sayre, and DM Dooley, Eur. J. Biochem., 269, 3645-3658 (2002).
• Structural correction of the 3-methylindole oxidatively-coupled dimer, KQ Ling, T Ren, JD Protasiewicz, LM Sayre, Tetrahedron Lett., 43, 6903-6905 (2002).
• 3-Pyrrolines are mechanism-based inactivators of the quinone-dependent amines oxidases but only substrates of the flavin-dependent amine oxidases, Y Lee, KQ Ling, X Lu, RB Silverman, EM Shepard, DM Dooley, and LM Sayre, J. Am. Chem. Soc., 124, 12135-12143 (2002).
• Copper(II)-Mediated Autoxidation of tert-Butylresorcinols, KQ Ling, Y Lee, D Macikenas, JD Protasiewicz, and LM Sayre, J. Org. Chem., 68, 1358-1366 (2003).
• Inactivation of bovine plasma amine oxidase by 4-aryloxy-2-butynamines and related analogs , H-B Jeon, G Sun, and LM Sayre, Biochim. Biophys. Acta, 1647, 343-354 (2003).
• Highly potent propargylamine and allylamine inhibitors of bovine plasma amine oxidase , H-B Jeon and LM Sayre, Biochem. Biophys. Res. Commun., 304, 788-794 (2003).
• Inhibition of bovine plasma amine oxidase by 1,4-diamino-2-butenes and -2-butynes , HB Jeon, Y Lee, C Qiao, H Huang, and LM Sayre, Bioorg. Med. Chem., 11, 4631-4641 (2003).
• Copper mediates dityrosine crosslinking of Alzheimer’s amyloid-b , CS Atwood, G Perry, H Zeng, Y Kato, WD Jones, KQ Ling, X Huang, RD Moir, D Wang, LM Sayre, MA Smith, S Chen, and AI Bush, Biochemistry, 43, 560-568 (2004).
• Cyanide as a copper and quinone-directed inhibitor of amine oxidases from Pisum sativum and Arthrobacter globiformis: Evidence for both copper coordination and cyanohydrin derivatization of the quinone cofactor , EM Shepard, GA Juda, KQ Ling, LM Sayre, and DM Dooley, J. Biol. Inorg. Chem., 9, 256-268 (2004).
• Selective inhibition of plasma amine oxidase by homopropargylamine, a new inactivator motif , C Qiao, HB Jeon, and LM Sayre, J. Am. Chem. Soc., 126, 8038-8045 (2004).
• Differential inhibition of six copper amine oxidases by a family of 4-(aryloxy)-2-butynamines: Evidence for a new mode of inactivation , K M O’Connell, DB Langley, EM Shepard, AP Duff, HB Jeon, G Sun, HC Freeman, JM Guss, LM Sayre, and DM Dooley, Biochemistry, 43, 10965-10978 (2004).
• 1,5-Diamino-2-pentyne is both a substrate and inactivator of plant copper amine oxidases. Z Lamplot, M Šebela, M Maloò, R Lenobel, K Lemr, J Havliš, P Peè, C Qiao, and LM Sayre, Eur. J. Biochem., 271, 4696-4708 (2004).
• Inhibition of murine N(1)-acetylated polyamine oxidase by an acetylenic amine and the allenic amine, MDL 72527. T Wu, K-Q Ling, LM Sayre, and WS McIntire, Biochem. Biophys. Res. Commun., 326, 483-490 (2005).
• Ligand dependence in the copper-catalyzed oxidation of hydroquinones. S. Mandal, NH Kazmi, and LM Sayre, Arch Biochem. Biophys., 435, 21-31 (2005).
• A dopaquinone model that mimics the water addition step of cofactor biogenesis in copper amine oxidases. KQ Ling and LM Sayre, J. Am. Chem. Soc., 127, 4777-4784 (2005).
• Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles. KQ Ling and LM Sayre, Bioorg. Med. Chem., 13, 3543-3551 (2005).
• Inactivation of bovine plasma amine oxidase by haloallylamines. J Kim, Y Zhang, C Ran, and LM Sayre, Bioorg. Med. Chem., 14, 1444-1453 (2006).
• Mechanism-based cofactor derivatization of a copper amine oxidase with a branched primary amine recruits the oxidase activity of the enzyme to turn inactivator into substrate. C. Qiao, K.-Q. Ling, E. M. Shepard, D. M. Dooley, L. M Sayre, J. Am. Chem. Soc., 128, 6206-6219 (2006).

Modification of Proteins in Aging and Degenerative Disease

• In situ oxidative catalysis by neurofibrillary tangles and senile plaques in Alzheimer disease: a central role for bound transition metals, MA Smith, G Perry, PLR Harris, Y Liu, KA Schubert, and LM Sayre, J. Neurochem., 74, 270-279 (2000).
• Polyclonal antibodies to a fluorescent 4-hydroxy-2-nonenal (HNE)-derived lysine-lysine crosslink. Characterization and application to HNE-modified protein and oxidized low density lipoprotein, G Xu, Y Liu, and LM Sayre, Chem. Res. Toxicol., 13, 406-413 (2000).
• HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are elevated in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques, RG Salomon, K Kaur, E Podrez, HF Hoff, AV Krushinsky, and LM Sayre, Chem. Res. Toxicol., 13, 557-564 (2000).
• In Alzheimer disease, heme oxygenase is coincident with Alz50, an epitope on tau induced by 4-hydroxy-2-nonenal modification, A Takeda, MA Smith, J Avila, A Nunomura. SL Siedlak, G Perry, and LM Sayre, J. Neurochem., 75, 1234-1241 (2000).
• Macrophage receptors responsible for distinct recognition of low density lipoprotein containing pyrrole and pyridinium adducts: models of oxidized, EA Podrez, G Hoppe, J. O’Neil, LM Sayre, N Sheibani, and HF Hoff, J. Lipid Res., 41, 1455-1463 (2000).
• Novel 2,5-hexanedione analogs. Substituent-induced control of protein cross-linking potential and oxidation susceptibility of the resulting primary amine-derived pyrroles, G Xu, MP Singh, D Gopal, and LM Sayre, Chem. Res. Toxicol., 14, 264-274 (2001).
• Chemistry and biochemistry of oxidative stress in neurodegenerative disease, LM Sayre, MA Smith, and G Perry, Curr. Med. Chem., 8, 721-738 (2001).
• Active glycation in neurofibrillary pathology of Alzheimer disease: N^e-(Carboxymethyl)lysine and hexitol lysine, RJ Castellani, PLR Harris, LM Sayre, J Fujii, N Taniguchi, MP Vitek, H Founds, CS Atwood, G Perry, and MA Smith, Free Radic. Biol. Med., 31, 175-180 (2001).
• Hydroxynonenal adducts indicate a role for lipid peroxidation in neocortical and brainstem Lewy bodies in humans, RJ Castellani, G Perry, SL Siedlak, A Nunomura, S Shimohama, J Zhang, T Montine, LM Sayre, and MA Smith, Neurosci. Lett. 319, 25-28 (2002).
• High molecular weight neurofilament proteins are physiological substrates of adduction by the lipid peroxidation product hydroxynonenal, T Wataya, A Nunomura, MA Smith, SL Siedlak, PLR Harris, S Shimohama, LI Szweda, MA Kaminski, J Avila, DL Price, DW Cleveland, LM Sayre, and G Perry, J. Biol. Chem., 277, 4644-4648 (2002).
• Crosslinking of proteins by 3-(trifluoromethyl)-2,5-hexanedione. Model studies implicate an unexpected amine-dependent defluorinative substitution pathway competing with pyrrole formation, G Xu and LM Sayre, J. Org. Chem., 67, 3007-3014 (2002).
• Triosidines: Novel Maillard reaction products and crosslinks from the reaction of glyceraldehydes with lysine and arginine residues, F Tessier, VM Monnier, LM Sayre, and JA Kornfield, Biochem. J., 369, 705-719 (2003).
• Model studies on the modification of proteins by lipoxidation-derived 2-hydroxyaldehydes, Z Liu and LM Sayre, Chem. Res. Toxicol., 16, 232-241 (2003).
• Model studies on protein side-chain modification by 4-oxo-2-nonenal, WH Zhang, J Liu, G Xu, Q Yuan, and LM Sayre, Chem. Res. Toxicol., 16, 512-523 (2003).
• Mass spectroscopic characterization of protein modification by 4-hydroxy-2-E-nonenal (HNE) and 4-oxo-2-E-nonenal (ONE), Z Liu, PE Minkler, and LM Sayre, Chem. Res. Toxicol., 16, 901-911 (2003).
• Carnosine inhibits (E)-4-hydroxy-2-nonenal-induced protein cross-linking: Structural characterization of carnosine-HNE adducts”, Y Liu, G Xu, and LM Sayre, Chem. Res. Toxicol., 16, 1589-1597 (2003).
• Copper mediates dityrosine crosslinking of Alzheimer’s amyloid-b, CS Atwood, G Perry, H Zeng, Y Kato, WD Jones, KQ Ling, X Huang, RD Moir, D Wang, LM Sayre, MA Smith, S Chen, and AI Bush, Biochemistry, 43, 560-568 (2004).
• Model studies on metal-catalyzed protein oxidation: structure of a possible His-Lys cross-link, Y Liu, G Sun, A David, and LM Sayre, Chem. Res. Toxicol., 17, 110-118 (2004).
• Synthesis of N,N-dimethyl-2,4-dinitro-5-fluorobenzylamine and its reactions with amino acids and peptides, Z Liu and LM Sayre, Tetrahedron, 60, 1601-1610 (2004).
• Derivatization of amino acids with N,N-dimethyl-2,4-dinitro-5-fluorobenzylamine for liquid chromatography/electrospray ionization mass spectrometry, Z Liu, PE Minkler, D Lin, and LM Sayre, Rapid Commun. Mass Spectrom., 18, 1-7 (2004).
• Synthesis and protein reactivity of 2E,4E,6E-dodecatrienal, C Ran, W Zhang, and LM Sayre, Tetrahedron Lett., 45, 7851-7853 (2004).
• Alzheimer-specific epitopes of tau represent lipid peroxidation induced conformations, Q Liu, MA Smith, J Avilá, J Debernardis, M Kansal, A Takeda, X Zhu, A Nunomura, K Honda, PI Moreira, CR Oliveira, MS Santos, S Shimohama, G Aliev, J de la Torre, HA Ghanbari, SL Siedlak, PLR Harris, LM Sayre, and G Perry, Free Radical Biol. Med., 38, 746-754 (2005).
• Mechanisms of DNA damage and repair in Alzheimer disease, VP Reddy, G Perry, MS Cooke, LM Sayre, and MA Smith, DNA Repair and Human Disease, AS Balajee (ed.), Springer, 2006, Chapter 8, pp. 99-114.
• 4-Oxo-2-nonenal is both more neurotoxic and protein reactive than 4-hydroxy-2-nonenal, D Lin, HG Lee, Q Liu, G Perry, MA Smith, LM Sayre, Chem. Res. Toxicol., 18, 1219-1231 (2005).
• Metal ions and oxidative protein modification in neurological disease, LM Sayre, PI Moreira, MA Smith, G Perry, Ann Ist Super Sanita, 41, 143-164 (2005).
• Detection of dideoxyosone intermediates in glycation using a monoclonal antibody: characterization of major epitope structures, S. Puttaiah, Y. Zhang, H. A. Pilch, C. Pfahler, T. Oya-Ito, L. M. Sayre, R. H. Nagaraj, Arch. Biochem. Biophys., 446, 186-196 (2006).
• Protein adducts generated from products of lipid oxidation: focus on HNE and ONE, Sayre LM, Lin D, Yuan Q, Zhu Z, Tang X. Drug Metab Rev 38, 651-75 (2006).
• Mass spectrometric evidence for long-lived protein adducts of 4-oxo-2-nonenal, X. Zhu, L. M. Sayre, Redox Report, in press (2006).
• Chemical nature of stochastic generation of protein-based carbonyls: metal-catalyzed oxidation vs. modification by products of lipid oxidation, Yuan Q, Zhu X, Sayre LM. Chem Res Toxicol. in press (2007).
• Long-lived 4-oxo-2-enal-derived apparent lysine Michael adducts are actually the isomeric 4-ketoamides, X Zhu, LM Sayre, Chem. Res. Toxicol. in press (2007).

 

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