The Burrows Research Group at the University of Utah

Publications

Chemistry in the Wasatch Mountains

 

M. E. Johansen, J. G. Muller, X. Xu, and C. J. Burrows, "Oxidatively induced DNA-protein cross-linking between single-stranded binding protein oligodeoxynucleotides containing 8-oxo-7,8-dihydro-2'-deoxyguanosine," Biochemistry, 2005, 44, 5660-5671.

O. Kornyushyna, A. J. Stemmler, D. M. Graybosch, I. Bergenthal, and C. J. Burrows, "Synthesis of a metallopeptide-PNA conjugate and its oxidative cross-linking to a DNA target," Bioconj. Chem. 2005, 16, 178-183.

M. E. Hosford, J. G. Muller, and C. J. Burrows, "Spermine participates in the oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation," J. Am. Chem. Soc. 2004, 126, 9540-9541.

S. Choi, R. B. Cooley, A. S. Hakemian, Y. C. Larrabee, R. C. Bunt, S. D. Maupas, J. G. Muller, and C. J. Burrows, “Mechanism of Two-Electron Oxidation of Deoxyguanosine-5'-monophosphate by a Platinum(IV) Complex,” J. Am. Chem. Soc. 2004, 126, 591-598.

C. J. Burrows, “Chlorine,” Chem. Eng. News 2003, 81, 62.

S. E. Rokita and C. J. Burrows, “Salen-Metal Complexes”, in Small Molecule DNA and RNA Binders, Demeunynck, M.; Bailly, C.; Wilson, W. D., Eds., Wiley-VCH: Weinheim, 2003, pp 126-145.

Y. Ye, J. G. Muller, W. Luo, C. L. Mayne, R. A. Jones and C. J. Burrows “Formation of 13C, 15N, and 18O-Labeled Guanidinohydantoin from Guanosine Oxidation with Singlet Oxygen. Implications for Structure and Mechanism,” J. Am. Chem. Soc. 2003, 125, 13926-13927.

O. Kornyushyna and C. J. Burrows, “Effect of the Oxidized Lesions Spiroiminodihydantoin and Guanidinohydantoin on Proofreading by Escherichia coli DNA Polymerase I (Klenow Fragment) in Different Sequence Contexts,” Biochemistry, 2003, 42, 13008-13018.

M. Leipold, H. Workman, J. G. Muller, C. J. Burrows, and S. S. David, “Recognition and Removal of Oxidized Guanines in Duplex DNA by the Base Excision Repair Enzymes hOGG1, yOGG1, and yOGG2,” Biochemistry, 2003, 42, 11373-11381.

P. T. Henderson, J. C. Delaney, J. G. Muller, W. L. Neeley, S. R. Tannenbaum, C. J. Burrows, and J. M. Essigmann, “The Hydantoin Lesions Formed from Oxidation of 7,8-Dihydro-8-oxoguanine are Potent Sources of Replication Errors in Vivo,” Biochemistry, 2003, 42, 9257-9262.

O. Kornyushyna, A. M. Berges, J. G. Muller, and C. J. Burrows, “In vitro nucleotide misinsertion opposite the oxidized guanosine lesions spiroiminodihydantoin and guanidinohydantoin and DNA synthesis past the lesions using E. coli polymerase I (Klenow fragment),” Biochemistry, 2002, 41, 15304-15314.

J. D. Van Horn, G. Bulaj, D. P. Goldenberg, and C. J. Burrows, “The Cys-Xaa-His Metal-Binding Motif. {N} vs. {S} Coordination and Nickel-Mediated Formation of Cysteinyl Sulfinic Acid,” J. Biol. Inorg. Chem. 2003, 8, 601-610.

R. A. Jameton, J. G. Muller, and C. J. Burrows, “Oxidative DNA damage from sulfite autoxidation catalyzed by manganese(III),” Comptes Rendus, Chimie, 2002, 5, 461-466.

C. J. Burrows, J. G. Muller, O. Kornyushyna, W. Luo, V. Duarte, M. D. Leipold, and S. S. David, “Structure and Potential Mutagenicity of New Hydantoin Products from Guanosine and 8-Oxo-7,8-dihydroguanosine Oxidation by Transition Metals,” Environ. Health Perspect. 2002, 110 Supp. 5, 713-717.

J. Cai, J. G. Muller, and C. J. Burrows, “Reactivity of bulged bases in duplex DNA with redox-active nickel and cobalt complexes,” Supramol. Chem. 2002, 14, 121-126.

W. Luo, J. G. Muller, and C. J. Burrows, “The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine,” Org. Lett. 2001, 3, 2801-2804.

W. Luo, J. G. Muller, E. M. Rachlin, and C. J. Burrows, “Characterization of Hydantoin Products from Oxidation of 8-Oxo-7,8-dihydroguanosine by One-electron Oxidants,” Chem. Res. Toxicol. 2001, 14, 927-938.

T. P. Hazra, J. G. Muller, R. C. Manuel, C. J. Burrows, R. S. Lloyd, and S. Mitra, “Repair of oxidation products of 8-oxoguanine by DNA glycosylases of E. coli,” Nucleic Acids Res. 2001, 29, 1967-1974.

M. Pitie, C. J. Burrows, B. Meunier, “Mechanisms of DNA cleavage by copper complexes of 3-Clip-Phen and of its conjugate with a distamycin analog,” Nucleic Acids Res. 2000, 28, 4856-4864.

M. Leipold, J. G. Muller, C. J. Burrows, and S. S. David, “The removal of hydantoin products of 8-oxoguanine oxidation by the E. coli DNA repair enzyme Fpg,” Biochemistry 2000, 39, 14984-14992.

A. J. Stemmler and C. J. Burrows, “Guanine vs. deoxyribose damage in DNA oxidation mediated by vanadium(IV) and vanadium(V) complexes,” J. Biol. Inorg. Chem. 2001, 6, 100-106.

M. Pitie, J. D. Van Horn, D. Brion, C. J. Burrows, and B. Meunier, “Targeting the DNA Cleavage Activity of Copper Phenanthroline and Clip-Phen to AT Tracts via Linkage to a Poly-N-methylpyrrole,” Bioconj. Chem., 2000, 12, 892-900.

S. E. Rokita and C. J. Burrows, “Nickel- and Cobalt-dependent Oxidation and Cross-linking of Proteins,” in Metal Ions in Biological Systems, Vol. 38, H. Sigel and A. Sigel, Eds., M. Dekker: New York, 2001, 289-311.

W. Luo, J. G. Muller, E. Rachlin, and C. J. Burrows, “Characterization of Spiroiminodihydantoin as a Product of 7,8-Dihydro-8-oxoguanosine Oxidation,” Org. Lett. 2000, 2, 613-616.

H.-C. Shih, H. Kassahun, C. J. Burrows, and S. E. Rokita, “Selective Association between a Macrocyclic Nickel Complex and Extrahelical Guanine Residues,” Biochemistry, 1999, 38, 15034-15042.

R. P. Hickerson, C. L. Chepanoske, S. D. Williams, S. S. David, and C. J. Burrows, “Mechanism-based DNA-Protein Cross-linking of MutY via Oxidation of 8-Oxoguanosine,” J. Am. Chem. Soc. 1999, 121, 9901-9902.

R. P. Hickerson, F. Prat, J. G. Muller, C. S. Foote, and C. J. Burrows, “Sequence and Stacking Dependence of 8-Oxoguanine Oxidation: Comparison of One-Electron vs. Singlet Oxygen Mechanisms,” J. Am. Chem. Soc. 1999, 121, 9423-9428.

N. Tang, J. G. Muller, C. J. Burrows, and S. E. Rokita, “Nickel and Cobalt Reagents Promote Selective Oxidation of Z-DNA,” Biochemistry, 1999, 38, 16648-16654.

A. J. Stemmler and C. J. Burrows, “The Sal-XH Motif for Metal-mediated Oxidative DNA-Peptide Cross-linking,” J. Am. Chem. Soc. 1999, 121, 6956-6957.

J. D. Van Horn and C. J. Burrows, “Formation of trans-3-hydroxy-4-phenylbutyrolactone from trans-styrylacetic acid and aqueous KHSO5,” Tetrahedron Lett. 1999, 40, 2069-2070.

J. G. Muller, L. A. Kayser, S. J. Paikoff, V. Duarte, N. Tang, S. E. Rokita, and C. J. Burrows, “Formation of DNA adducts using nickel(II) complexes of redox-active ligands: A comparison of salen and peptide complexes,” Coord. Chem. Rev. 1999, 185-186, 761-774.

V. Lepentsiotis, J. Domagala, I. Grgic, R. van Eldik, J. G. Muller, and C. J. Burrows, “Mechanistic information on the redox cycling of Ni(II/III) complexes in the presence of sulfur oxides and oxygen. Correlation with DNA damage experiments,” Inorg. Chem. 1999, 38, 3500-3505.

V. Duarte, J. G. Muller and C. J. Burrows, “Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine,” Nucleic Acids Res. 1999, 27, 496-502.

R. P. Hickerson, V. Duarte, J. D. Van Horn, R. J. Perez, J. G. Muller, S. E. Rokita, and C. J. Burrows, “DNA cleavage vs. cross-linking using nickel peptides: Mechanistic aspects,” Metals and Genetics, B. Sarkar, Ed., Plenum: New York, 1999, 183-196.

S. E. Rokita and C. J. Burrows, “Probing nucleic acid structure with nickel and cobalt-based reagents,” Current Protocols in Nucleic Acid Chemistry, 2000, 6.4.1-6.4.7.

K. Wietzerbin, J. G. Muller, R. A. Jameton, G. Pratviel, J. Bernadou, B. Meunier, and C. J. Burrows, “Hydroxylation, Epoxidation and DNA Cleavage Reactions Mediated by the Biomimetic MnTMPyP/O2/Sulfite Oxidation System,” Inorg. Chem. 1999, 38, 4123-4127.

J. G. Muller, V. Duarte, R. P. Hickerson, and C. J. Burrows, “Gel electrophoretic detection of 7,8-dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine via oxidation by Ir(IV),” Nucleic Acids Res. 1998, 26, 2247-2249.

R. P. Hickerson, C. D. Watkins-Sims, C. J. Burrows, J. F. Atkins, R. F. Gesteland, and B. Felden, “A Nickel Complex Cleaves Uridines in Folded RNA Structures: Application to E. coli tmRNA and Related Engineered Molecules,” J. Mol. Biol. 1998, 279, 577-587.

P. Zheng, C. J. Burrows, and S. E. Rokita, “Nickel- and Cobalt-Dependent Reagents Identify Structural Features of RNA that are not Detected by Dimethyl Sulfate or RNase T1,” Biochemistry 1998, 37, 2207-2214.

S. A. Ross and C. J. Burrows, “Nickel(II) Complexes of Cysteine- and Cystine-containing Peptides: Spontaneous Formation of Disulfide-Bridged Dimers at Neutral pH,” Inorg. Chem. 1998, 37, 5358-5363.

H.-C. Shih, N. Tang, C. J. Burrows and S. E. Rokita, “Nickel-based Probes of Nucleic Acid Structure Bind to Guanine N7 but do not Perturb the Dynamic Equilibrium of Extrahelical Guanine Residues,” J. Am. Chem. Soc. 1998, 120, 3284-3288.

J. G. Muller and C. J. Burrows, “Metallodrug complexes that mediate DNA and lipid damage via sulfite autoxidation: Copper(II) famotidine and iron(III) bis(salicylglycine),” Inorg. Chim. Acta 1998, 275-276, 314-319.

C. J. Burrows and J. G. Muller, "Oxidative Nucleobase Modifications Leading to Strand Scission," Chem. Rev. 1998, 98, 1109-1152.

R. J. Perez, J. G. Muller, S. E. Rokita, and C. J. Burrows, “Oxidative DNA Damage Mediated by Metal-Peptide Complexes,” Pure Appl. Chem. 1998, 70, 275-278.

S. A. Ross and C. J. Burrows, "Bromination of Pyrimidines using Bromide and Monoperoxysulfate: A Competition Study between Cytidine, Thymidine, and Uridine," Tetrahedron Lett.1997, 38, 2805-2808.

J. G. Muller, R. P. Hickerson, R. J. Perez, and C. J. Burrows, "DNA Damage from Sulfite Autoxidation Catalyzed by a Nickel(II) Peptide," J. Am. Chem. Soc. 1997, 119, 1501-1506.

G. Gill, A. A. Richter-Rusli, C. J. Burrows, and S. E. Rokita, "Nickel-Dependent Crosslinking of a Protein," J. Chem. Toxicol. 1997, 10, 302-309.

S. A. Ross and C. J. Burrows, "Cytosine-specific Chemical Probing of DNA using Bromide and Monoperoxysulfate," Nucl. Acids Res. 1996, 24, 5062-5063.

G. A. McLachlan, J. G. Muller, S. E. Rokita, and C. J. Burrows, "Metal-Mediated Oxidation of Guanines in DNA and RNA: A Comparison of Cobalt(II), Nickel(II), and Copper(II) Complexes," Inorg. Chem. Acta 1996, 251, 193-199.

C. J. Burrows, J. G. Muller, G. T. Poulter and S. E. Rokita, "Nickel-Catalyzed Oxidations: From Hydrocarbons to DNA," Acta Chem. Scand. 1996, 50, 337-344.

J. G. Muller, P. Zheng, S. E. Rokita, and C. J. Burrows, "DNA and RNA Modification Promoted by [Co(H2O)6]Cl2: Guanine Selectivity, Temperature Dependence and Mechanism," J. Am. Chem. Soc. 1996, 118, 2320-2325.

W. Nam, S. J. Baek, K. A. Lee, B. T. Ahn, J. G. Muller, C. J. Burrows, and J. S. Valentine, "Nickel Complexes as Antioxidants. Inhibition of Aldehyde Autoxidation by Nickel(II) Tetraazamacrocycles," Inorg. Chem. 1996, 35, 6632-6633.

C. J. Burrows and S. E. Rokita, "Nickel Complexes as Probes of Guanine Sites in Nucleic Acid Folding," in Metal Ions in Biological Systems, Vol.33, H. Sigel and A. Sigel, Eds., M. Dekker: New York, 1995, Chap. 18, pp537-560.

J. G. Muller, M. M. P. Ng, and C. J. Burrows, "Hydrophobic vs. Coulombic Interactions in the Binding of Steroidal Polyamines to DNA," J. Molec. Recognit. 1996, 9, 143-148.

C. J. Burrows, J. G. Muller, H.-C. Shih, and S. E. Rokita, "Interaction of Metal Complexes with B vs. Z DNA," in "Supramolecular Stereochemistry," J. S. Siegel, Ed.; Kluwer: Dordrecht, 1995, pp 57-62.

H. P. Hsieh, J. G. Muller, and C. J. Burrows, "Synthesis and DNA Binding Properties of C3-, C12-, and C24-Substituted Amino-Steroids Derived from Bile Acids," Bioorg. Med. Chem. 1995, 3, 823-838.

S. E. Rokita, P. Zheng, N. Tang, C.-C. Cheng, R.-H. Yeh, J. G. Muller and C. J. Burrows, "Nickel Complexes in Modification of Nucleic Acids," In Genetic Response to Metals, B. Sarkar, Ed.; M. Dekker: New York, 1995, pp 201-216.

C. J. Burrows and S. E. Rokita, "Recognition of Guanine Structure in Nucleic Acids by Nickel Complexes," Acc. Chem. Res. 1994, 27, 295-301.

H. P. Hsieh, J. G. Muller, and C. J. Burrows, "Structural Effects in Novel Steroidal Polyamine-DNA Binding," J. Am. Chem. Soc. 1994, 116, 12077-12078.

K. J. Fordon, C. G. Crane, and C. J. Burrows, "A Novel Method for the Synthesis of 5-Substituted 6-Membered Cyclic Ureas," Tetrahedron Lett. 1994, 35, 6215-6216.

S. M. Evans, C. A. Venanzi and C. J. Burrows, "Design of Cholic Acid Hosts for Molecular Recognition of Glucose using Systematic conformational Searching," J. Molec. Struct. (THEOCHEM), 1994, 308, 159-174.

J. G. Muller, S. J. Paikoff, S. E. Rokita and C. J. Burrows, "DNA Modification Promoted by Water-Soluble Nickel(II) Salen Complexes: A Switch to DNA Alkylation," J. Inorg. Biochem. 1994, 54, 199-206.

C. C. Cheng, S. E. Rokita, and C. J. Burrows, "Nickel(III)-Promoted DNA Scission using Ambient Dioxygen" Angew. Chem. 1993, 105, 290-292, and Angew. Chem. (Int. Ed. Engl.) 1993, 32, 277-278.

J. G. Muller, X. Chen, A. C. Dadiz, S. E. Rokita, and C. J. Burrows, "Macrocyclic Nickel Complexes in DNA Recognition and Oxidation," Pure Appl. Chem. 1993, 65, 545-550.

S. J. Wey, K. J. O'Connor, and C. J. Burrows, "Preparation of Primary Vicinal Diamines from Amino Acid Esters and Crystal Structure of a Chiral Nickel Salen Complex," Tetrahedron Lett. 1993, 34, 1905-1908.

X. Chen, S. Woodson, C. J. Burrows and S. E. Rokita, "A Highly Sensitive Probe for Guanine N7 in Folded Structures of RNA: Application to tRNAPhe and Tetrahymena Group I Intron," Biochemistry, 1993, 32, 7610-7616.

S. A. Woodson, J. G. Muller, C. J. Burrows and S. E. Rokita, "A Primer Extension Assay for Modification of Guanine N7 by Ni(II) Complexes," Nucl. Acids Res. 1993, 21, 5524-5525.

X. Chen, C. J. Burrows, and S. E. Rokita, "Conformation Specific Oxidation of Guanosine in DNA: Ends, Mismatches, Bulges, and Loops," J. Am. Chem. Soc. 1992, 114, 322-325.

K. J. O'Connor, S. J. Wey and C. J. Burrows, "Alkene Aziridination and Epoxidation Catalyzed by Chiral Metal Salen Complexes," Tetrahedron Lett. 1992, 33, 1001-1004.

J. G. Muller, X. Chen, A. C. Dadiz, S. E. Rokita, and C. J. Burrows, "Ligand Effects Associated with the Intrinsic Selectivity of DNA Oxidation Promoted by Nickel(II) Macrocyclic Complexes," J. Am. Chem. Soc. 1992, 114, 6407-6411.

X. Chen, S. E. Rokita and C. J. Burrows, "DNA Modification: Intrinsic Selectivity of Nickel(II) Complexes," J. Am. Chem. Soc. 1991, 113, 5884-5886.

C. A. Salata, M. T. Youinou, and C. J. Burrows, "Preparation and Structural Characterization of Dicopper(II) and Dinickel(II) Imidazolate-Bridged Macrocyclic Schiff Base Complexes," Inorg. Chem. 1991, 30, 3454-3461.

K. J. O'Connor and C. J. Burrows, "Catalysis of Aryl Halogen Exchange by Nickel(II) Complexes using NaOCl," J. Org. Chem. 1991, 56, 1344-1346.

H. Yoon, T. R. Wagler, K. J. O'Connor and C. J. Burrows, "High Turnover Rates in pH-Dependent Alkene Epoxidation using NaOCl and Square Planar Nickel(II) Catalysts," J. Am. Chem. Soc. 1990, 112, 4568-4570.

H. S. Ham and C. J. Burrows, "Synthesis of a New Molecular Receptor Based on Cholic Acid," Taehan Hwahakhoe Chi 1990, 34, 215-216.

C. J. Burrows, "Catalytic Reactions of Macrocyclic Nickel(II) Complexes," in Inclusion Phenomena and Molecular Recognition, Atwood, J. L., Ed.; Plenum: New York, 1990; 199-207.

C. A. Salata, M. T. Youinou, and C. J. Burrows, "(Template)2 Synthesis of a Dinucleating Macrocyclic Ligand and Crystal Structure of its Dicopper(II) Imidazolate Complex," J. Am. Chem. Soc. 1989, 111, 9278-9279.

S. M. Evans, C. J. Burrows, and C. A. Venanzi, "Design of Cholic Acid Macrocycles as Hosts for Molecular Recognition of Monosaccharides," J. Molec. Struct. (THEOCHEM), 1995, 334, 193-205.

T. R. Wagler, Y. Fang and C. J. Burrows, "Optically Active Difunctionalized Dioxocyclam Macrocycles. Ligands for Nickel-Catalyzed Oxidation of Alkenes," J. Org. Chem. 1989, 54, 1584-1589.

J. F. Kinneary, T. M. Roy, J. S. Albert, H. Yoon, T. R. Wagler, L. Shen and C. J. Burrows, "Progress Toward Artificial Metalloenzymes: New Ligands for Transition Metal Ions and Neutral Molecules," J. Inclusion Phenom. 1989, 7, 155-168.

H. Yoon and C. J. Burrows, "Catalysis of Olefin Oxidation by Nickel Salen Complexes Using NaOCl under Phase Transfer Conditions," J. Am. Chem. Soc., 1988, 110, 4087-4089.

T. R. Wagler and C. J. Burrows, "Synthesis of a Chiral Dioxocyclam Derived from L-Phenylalanine and its Application to Olefin Oxidation Chemistry," Tetrahedron Lett. 1988, 29, 5091-5094.

J. F. Marecek, P. A. Fischer and C. J. Burrows, "Complexation of ATP to a Synthetic [15]-N3 Macrocyclic Polyammonium Receptor," Tetrahedron Lett. 1988, 29, 6231-6234.

J. F. Kinneary, J. S. Albert and C. J. Burrows, "Mechanistic Studies of Alkene Epoxidation Catalyzed by Nickel(II) Cyclam Complexes. 18O-Labeling and Substituent Effects," J. Am. Chem. Soc. 1988, 110, 6124-6129.

J. F. Kinneary, T. R. Wagler and C. J. Burrows, "Alkene Epoxidation Using Ni(II) Complexes of Chiral Cyclams," Tetrahedron Lett. 1988, 29, 877-880.

C. A. Salata, D. Van Engen and C. J. Burrows, "Synthesis and Structure of a Semi-Rigid Dinucleating Macrocycle containing the 2,6-Di(thiomethyl)pyridine Unit and Reactions of its Cu(II) Complex," J. Chem. Soc., Chem. Commun. 1988, 579-580.

C. J. Burrows and R. A. Sauter, "Synthesis and Conformational Studies of a New Host System Based on Cholic Acid," J. Inclusion Phenom. 1987, 5, 117-121.

T. R. Wagler and C. J. Burrows, "Synthesis of an Optically Active C-Functionalized Cyclam, (S)-5-(Hydroxymethyl)-1,4,8,11-tetraazacyclotetradecane and its Ni(II) Complex," J. Chem. Soc., Chem. Commun. 1987, 277-278.

J. F. Marecek and C. J. Burrows, "Synthesis of an Optically Active Spermine Macrocycle, (S)-6-(Hydroxymethyl)-1,5,10,14-tetraazacyclooctadecane, and its Complexation to ATP" Tetrahedron Lett. 1986, 27, 5943-5946.

J. P. Behr, C. J. Burrows, R. Heng, and J. M. Lehn, "Synthesis of Novel Macrobicyclic Polyfunctional Cryptands," Tetrahedron Lett. 1985, 26, 215-218.

C. J. Burrows and B. K. Carpenter, "Substituent Effects on the Aliphatic Claisen Rearrangement. 2. Theoretical Analysis" J. Am. Chem. Soc. 1981, 103, 6984-6986.

C. J. Burrows and B. K. Carpenter, "Substituent Effects on the Aliphatic Claisen Rearrangement. 1. Synthesis and Rearrangement of Cyano-Substituted Allyl Vinyl Ethers" J. Am. Chem. Soc. 1981, 103, 6983-6984.