L M Sayre

Summary

Affiliation: Case Western Reserve University
Country: USA

Publications

  1. ncbi request reprint Model studies on the metal-catalyzed protein oxidation: structure of a possible His-Lys cross-link
    Yahua Liu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 17:110-8. 2004
  2. ncbi request reprint Redox metals and neurodegenerative disease
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH44106, USA
    Curr Opin Chem Biol 3:220-5. 1999
  3. ncbi request reprint Metal ions and oxidative protein modification in neurological disease
    Lawrence M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    Ann Ist Super Sanita 41:143-64. 2005
  4. ncbi request reprint Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 9:1194-201. 1996
  5. ncbi request reprint In situ oxidative catalysis by neurofibrillary tangles and senile plaques in Alzheimer's disease: a central role for bound transition metals
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Neurochem 74:270-9. 2000
  6. ncbi request reprint Chemistry and biochemistry of oxidative stress in neurodegenerative disease
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    Curr Med Chem 8:721-38. 2001
  7. pmc Iron accumulation in Alzheimer disease is a source of redox-generated free radicals
    M A Smith
    Institute of Pathology, Case Western Reserve University, Cleveland, OH 44106, USA
    Proc Natl Acad Sci U S A 94:9866-8. 1997
  8. ncbi request reprint Active glycation in neurofibrillary pathology of Alzheimer disease: N(epsilon)-(carboxymethyl) lysine and hexitol-lysine
    R J Castellani
    Institute of Pathology, Case Western Reserve University, Cleveland, OH 44106, USA
    Free Radic Biol Med 31:175-80. 2001
  9. ncbi request reprint HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are more prevalent in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques
    R G Salomon
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106 7078, USA
    Chem Res Toxicol 13:557-64. 2000
  10. ncbi request reprint Tetraphenylborate potentiates the respiratory inhibition by the dopaminergic neurotoxin MPP+ in both electron transport particles and intact mitochondria
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106
    Biochem Biophys Res Commun 161:809-18. 1989

Collaborators

Detail Information

Publications46

  1. ncbi request reprint Model studies on the metal-catalyzed protein oxidation: structure of a possible His-Lys cross-link
    Yahua Liu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 17:110-8. 2004
    ..Possible mechanisms for formation of the cross-link and other observed products are discussed...
  2. ncbi request reprint Redox metals and neurodegenerative disease
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH44106, USA
    Curr Opin Chem Biol 3:220-5. 1999
    ....
  3. ncbi request reprint Metal ions and oxidative protein modification in neurological disease
    Lawrence M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    Ann Ist Super Sanita 41:143-64. 2005
    ....
  4. ncbi request reprint Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 9:1194-201. 1996
    ..Potential advantages of antibodies recognizing "advanced lipid peroxidation end products" over those recognizing "early" HNE adduction products are discussed...
  5. ncbi request reprint In situ oxidative catalysis by neurofibrillary tangles and senile plaques in Alzheimer's disease: a central role for bound transition metals
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Neurochem 74:270-9. 2000
    ....
  6. ncbi request reprint Chemistry and biochemistry of oxidative stress in neurodegenerative disease
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    Curr Med Chem 8:721-38. 2001
    ..Delineation of the profile of oxidative damage in each disease will provide clues to how the specific neuronal populations are differentially affected by the individual disease conditions...
  7. pmc Iron accumulation in Alzheimer disease is a source of redox-generated free radicals
    M A Smith
    Institute of Pathology, Case Western Reserve University, Cleveland, OH 44106, USA
    Proc Natl Acad Sci U S A 94:9866-8. 1997
    ..Taken together, these findings indicate that iron accumulation could be an important contributor toward the oxidative damage of Alzheimer disease...
  8. ncbi request reprint Active glycation in neurofibrillary pathology of Alzheimer disease: N(epsilon)-(carboxymethyl) lysine and hexitol-lysine
    R J Castellani
    Institute of Pathology, Case Western Reserve University, Cleveland, OH 44106, USA
    Free Radic Biol Med 31:175-80. 2001
    ..Our findings support the notion that aldehyde-mediated modifications, together with oxyradical-mediated modifications, are critical pathogenic factors in AD...
  9. ncbi request reprint HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are more prevalent in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques
    R G Salomon
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106 7078, USA
    Chem Res Toxicol 13:557-64. 2000
    ..Therefore, HNE-pyrrole epitopes provide a more indelible marker of oxidative injury than levels of free HNE...
  10. ncbi request reprint Tetraphenylborate potentiates the respiratory inhibition by the dopaminergic neurotoxin MPP+ in both electron transport particles and intact mitochondria
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106
    Biochem Biophys Res Commun 161:809-18. 1989
    ..It is suggested that TPB- facilitates access of MPP+ to its intramembrane site of inhibitory action in Complex I...
  11. ncbi request reprint Novel 2,5-hexanedione analogues. Substituent-induced control of the protein cross-linking potential and oxidation susceptibility of the resulting primary amine-derived pyrroles
    G Xu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 14:264-74. 2001
    ..As these two gamma-diketones possess aqueous-organic partitioning properties similar to those of 2,5-HD, they should serve as useful mechanistic probes in further studies...
  12. ncbi request reprint Regulation of the biosynthesis of N-acetylglucosaminylpyrophosphoryldolichol, feedback and product inhibition
    E L Kean
    Department of Ophthalmology, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Biol Chem 274:34072-82. 1999
    ..This network of inhibitory and stimulatory influences may be aspects of metabolic control of the pathway and thus of glycoprotein biosynthesis in general...
  13. ncbi request reprint 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
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Org Chem 66:1925-37. 2001
    ..The latter undergoes a rapid, but noninstantaneous reoxygenation at C5 to restore the active cofactor form, also probably mediated by the active-site copper...
  14. ncbi request reprint Dopaminergic neurotoxicity in vivo and inhibition of mitochondrial respiration in vitro by possible endogenous pyridinium-like substances
    L M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106
    J Neurochem 57:2106-15. 1991
    ..Relative to MPP+, all compounds tested had weak dopaminergic uptake activity in vitro and weak dopaminergic toxicity in vivo, consistent with other findings of relatively low neurotoxic potential for presumed endogenous pyridiniums...
  15. ncbi request reprint Identification and expression of the Na+/H+ exchanger in mammalian cerebrovascular and choroidal tissues: characterization by amiloride-sensitive [3H]MIA binding and RT-PCR analysis
    R N Kalaria
    Department of Neurology, Case Western Reserve University School of Medicine, Cleveland, OH 44106, USA
    Brain Res Mol Brain Res 58:178-87. 1998
    ..Our study suggests that mammalian cerebrovascular and choroidal tissues contain high amounts of the ubiquitous amiloride-sensitive [3H]MIA binding proteins consistent with the expression of NHE type 1 mRNA...
  16. ncbi request reprint Catalytic turnover of benzylamine by a model for the lysine tyrosylquinone (LTQ) cofactor of lysyl oxidase
    K Q Ling
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Am Chem Soc 123:9606-11. 2001
    ..The mechanism of the overall reaction profile was elucidated by a combination of optical and NMR spectroscopy and O(2) uptake studies...
  17. ncbi request reprint Carnosine inhibits (E)-4-hydroxy-2-nonenal-induced protein cross-linking: structural characterization of carnosine-HNE adducts
    Yahua Liu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 16:1589-97. 2003
    ..The main carnosine-HNE adduct is shown to be a 13-member cyclic adduct formed through initial Schiff base formation followed by conjugate addition of the imidazole group...
  18. ncbi request reprint Copper mediates dityrosine cross-linking of Alzheimer's amyloid-beta
    Craig S Atwood
    Institute of Pathology, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Biochemistry 43:560-8. 2004
    ..Given the elevated concentration of Cu in senile plaques, our results suggest that Cu interactions with Abeta could be responsible for causing the covalent cross-linking of Abeta in these structures...
  19. ncbi request reprint Alzheimer-specific epitopes of tau represent lipid peroxidation-induced conformations
    Quan Liu
    Institute of Pathology, Case Western Reserve University, 2085 Adelbert Road, Cleveland, OH 44106, USA
    Free Radic Biol Med 38:746-54. 2005
    ....
  20. ncbi request reprint Chemical nature of stochastic generation of protein-based carbonyls: metal-catalyzed oxidation versus modification by products of lipid oxidation
    Quan Yuan
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 20:129-39. 2007
    ..Additional studies carried out to clarify the potential use of DNPH derivatization to tag peptide-based carbonyls for mass spectrometric analysis revealed that DNPH derivatization can reverse under the conditions used for proteolysis...
  21. ncbi request reprint 4-Oxo-2-nonenal is both more neurotoxic and more protein reactive than 4-hydroxy-2-nonenal
    De Lin
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 18:1219-31. 2005
    ..The greater neurotoxicity of ONE could reflect in part the different reactivity characteristics of ONE as compared to HNE...
  22. ncbi request reprint Protein adducts generated from products of lipid oxidation: focus on HNE and one
    Lawrence M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Drug Metab Rev 38:651-75. 2006
    ..It appears that lipid oxidation is a more important contributor to such activity than metal-catalyzed oxidation of protein side-chains...
  23. ncbi request reprint Oxidative stress and neurotoxicity
    Lawrence M Sayre
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 21:172-88. 2008
    ..Following a review of oxidative stress involvement in individual disease states, some conclusions are provided as to what further research should hope to accomplish in the field...
  24. ncbi request reprint Hydroxynonenal, toxic carbonyls, and Alzheimer disease
    Quan Liu
    Institute of Pathology, Case Western Reserve University, 2085 Adelbert Road, Cleveland, OH 44106, USA
    Mol Aspects Med 24:305-13. 2003
    ..Hopefully, the following discussion will help elucidate the relationship between oxidative stress, protein modification and the pathogenesis of AD...
  25. ncbi request reprint Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal
    Zhongfa Liu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 16:901-11. 2003
    ....
  26. ncbi request reprint Model studies on protein side chain modification by 4-oxo-2-nonenal
    Wei han Zhang
    Department of Chemistry, Case Western Reserve University, Cleveland Ohio 44106, USA
    Chem Res Toxicol 16:512-23. 2003
    ..Mechanisms of both nonoxidative and oxidative side chain reactions of ONE are discussed, as is the relative propensity (ONE > HNE) to induce cross-linking of the model proteins ribonuclease A and beta-lactoglobulin...
  27. ncbi request reprint High molecular weight neurofilament proteins are physiological substrates of adduction by the lipid peroxidation product hydroxynonenal
    Takafumi Wataya
    Institute of Pathology and Departments of Physiology and Biophysics, and Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Biol Chem 277:4644-8. 2002
    ....
  28. ncbi request reprint Hydroxynonenal adducts indicate a role for lipid peroxidation in neocortical and brainstem Lewy bodies in humans
    Rudy J Castellani
    Institute of Pathology, Case Western Reserve University, 2085 Adelbert Road, Cleveland, OH 44106, USA
    Neurosci Lett 319:25-8. 2002
    ..These findings not only support prior studies indicating that lipid peroxidation is increased in patients with PD and DLBD but that oxidative damage may play a critical role in Lewy body formation...
  29. ncbi request reprint Amyloid-beta, tau alterations and mitochondrial dysfunction in Alzheimer disease: the chickens or the eggs?
    Mark A Smith
    Institute of Pathology, Case Western Reserve University, 2085 Adelbert Road, Cleveland, OH 44106, USA
    Neurochem Int 40:527-31. 2002
    ..However, this rationale may be misguided since new evidence from our laboratories and others suggest that the lesions not only occur as a by-product of the fundamental disease process but also that they may be protective...
  30. ncbi request reprint The role of iron and copper in the aetiology of neurodegenerative disorders: therapeutic implications
    George Perry
    Institute of Pathology, Case Western Reserve University, Cleveland, Ohio 44106, USA
    CNS Drugs 16:339-52. 2002
    ..In this article, we examine not only the possible mechanism of disease but also how pharmaceuticals may intervene, from direct and indirect antioxidant therapy to strategies involving gene therapy...
  31. ncbi request reprint Model studies on the modification of proteins by lipoxidation-derived 2-hydroxyaldehydes
    Zhongfa Liu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 16:232-41. 2003
    ..5 mM 2-hydroxyheptanal for 10 days at 25 degrees C. The 4-alkylimidazolium is proposed to contribute to the protein cross-linking observed by gel electrophoresis in the incubation of RNase with higher concentrations of 2-hydroxyheptanal...
  32. ncbi request reprint Is oxidative damage the fundamental pathogenic mechanism of Alzheimer's and other neurodegenerative diseases?
    George Perry
    Institute of Pathology, Case Western Reserve University, Cleveland, OH 44106, USA
    Free Radic Biol Med 33:1475-9. 2002
    ..Although much data remain to be collected, the broad spectrum of changes found in AD are only seen, albeit to a lesser extent, in normal aging with other neurodegenerative diseases showing distinct spectrums of change...
  33. ncbi request reprint Selective inhibition of bovine plasma amine oxidase by homopropargylamine, a new inactivator motif
    Chunhua Qiao
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Am Chem Soc 126:8038-45. 2004
    ..25 microM. Rat liver mitochondrial monoamine oxidase was also inactivated by 4, as expected, but only very weakly by 1. Potential mechanisms explaining the selective inhibition of BPAO by 1 are discussed...
  34. ncbi request reprint Synthesis of six epoxyketooctadecenoic acid (EKODE) isomers, their generation from nonenzymatic oxidation of linoleic acid, and their reactivity with imidazole nucleophiles
    De Lin
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    J Org Chem 72:9471-80. 2007
    ..The synthesis of the EKODE isomers makes these important molecules available for further chemical and biological evaluation...
  35. ncbi request reprint Long-lived 4-oxo-2-enal-derived apparent lysine michael adducts are actually the isomeric 4-ketoamides
    Xiaochun Zhu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Chem Res Toxicol 20:165-70. 2007
    ..The same type of 4-ketoamide represents the apparent Michael adduct on Lys residues formed by the carboxy-terminating ONE-like 4-oxo-2-enal arising along with ONE from the oxidation of linoleic acid...
  36. ncbi request reprint Mass spectrometric evidence for long-lived protein adducts of 4-oxo-2-nonenal
    Xiaochun Zhu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    Redox Rep 12:45-9. 2007
    ..The Lys-ketoamide and His-Lys imidazolylpyrrole cross-links appear to be unusually prominent markers of stable protein modification by ONE...
  37. ncbi request reprint Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles
    Ke Qing Ling
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    Bioorg Med Chem 13:3543-51. 2005
    ....
  38. ncbi request reprint Copper(II)-mediated autoxidation of tert-butylresorcinols
    Ke Qing Ling
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Org Chem 68:1358-66. 2003
    ..The key step appears to be equilibration of a copper(II)-resorcinolate with a charge-transfer radical form that reacts regioselectively with O(2) as prescribed by resonance...
  39. ncbi request reprint Detection of dideoxyosone intermediates of glycation using a monoclonal antibody: characterization of major epitope structures
    Shivaprakash Puttaiah
    Department of Ophthalmology, Case Western Reserve University, Cleveland, OH 44106, USA
    Arch Biochem Biophys 446:186-96. 2006
    ..Our study confirms that dideoxyosone intermediates form during glycation and offers a new tool for the study of this important pathway in diabetes and aging...
  40. ncbi request reprint Cross-linking of proteins by 3-(trifluoromethyl)-2,5-hexanedione. Model studies implicate an unexpected amine-dependent defluorinative substitution pathway competing with pyrrole formation
    Guozhang Xu
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Org Chem 67:3007-14. 2002
    ....
  41. ncbi request reprint Cyanide as a copper and quinone-directed inhibitor of amine oxidases from pea seedlings ( Pisum sativum) and Arthrobacter globiformis: evidence for both copper coordination and cyanohydrin derivatization of the quinone cofactor
    Eric M Shepard
    Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA
    J Biol Inorg Chem 9:256-68. 2004
    ..In spite of cyanohydrin derivatization of the TPQ cofactor in these enzymes, the uncompetitive inhibition of amine oxidation is determined to arise almost exclusively through CN(-) complexation of Cu(I)...
  42. ncbi request reprint A dopaquinone model that mimics the water addition step of cofactor biogenesis in copper amine oxidases
    Ke Qing Ling
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    J Am Chem Soc 127:4777-84. 2005
    ..This study represents the first chemical demonstration of a true o-quinone hydration, which occurs in cofactor biogenesis in copper amine oxidases...
  43. pmc Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues
    Frederic J Tessier
    Department of Chemical Engineering, California Institute of Technology, 1200 East Colarado Blvd, Pasadena, CA 91125, USA
    Biochem J 369:705-19. 2003
    ....
  44. ncbi request reprint Ligand dependence in the copper-catalyzed oxidation of hydroquinones
    Subrata Mandal
    Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA
    Arch Biochem Biophys 435:21-31. 2005
    ..Thus, the rapid copper(II)-catalyzed reaction operating aerobically does not involve a simple ping-pong reduction of copper(II) to copper(I) by hydroquinone and reoxidation of copper(I) by O(2)...
  45. ncbi request reprint 1,5-diamino-2-pentyne is both a substrate and inactivator of plant copper amine oxidases
    Zbynek Lamplot
    Department of Biochemistry, Faculty of Science, Palacky University, Olomouc, Czech Republic
    Eur J Biochem 271:4696-708. 2004
    ..Finally, N-(2,3-dihydropyridinyl)-1,5-diamino-2-pentyne was identified by means of 1H- and 13C-NMR experiments. This structure suggests a lysine modification chemistry that could be responsible for the observed inactivation...
  46. doi request reprint Oxidations of N-(3-indoleethyl) cyclic aliphatic amines by horseradish peroxidase: the indole ring binds to the enzyme and mediates electron-transfer amine oxidation
    Ke Qing Ling
    Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA
    J Am Chem Soc 130:933-44. 2008
    ..This is the first systematic investigation to document aliphatic amine oxidation by HRP at rates consistent with normal metabolic turnover, and the demonstration that this is facilitated by an auxiliary electron-rich aromatic ring...