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Angewandte Chemie International Edition
Communication

A Purine‐like Nickel(II) Base Pair for DNA*

Christopher Switzer Prof.

E-mail address:christopher.switzer@ucr.edu

Department of Chemistry, University of California, Riverside, CA 92521, USA, Fax: (+1) 951‐787‐2435

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Surajit Sinha

Department of Chemistry, University of California, Riverside, CA 92521, USA, Fax: (+1) 951‐787‐2435

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Paul H. Kim

Department of Chemistry, University of California, Riverside, CA 92521, USA, Fax: (+1) 951‐787‐2435

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Benjamin D. Heuberger

Department of Chemistry, University of California, Riverside, CA 92521, USA, Fax: (+1) 951‐787‐2435

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First published: 22 February 2005
Cited by: 109
*

This work was supported by DOD/DARPA/DMEA under award no. DMEA90‐02‐2‐0216 and the NASA exobiology program under award no. NAG5‐9812.

Abstract

Metal in the middle: A metallo base pair incorporating 6‐pyridylpurine (Purp) was synthesized and characterized. PurP binds nickel(II) preferentially over other divalent ions and yields a base pair that is more stable than natural Watson–Crick pairs with high mismatch selectivity. Computational studies support a dimensional resemblance between PurP⋅Ni2+⋅PurP (see structure) and natural base pairs.

Number of times cited: 109

  • , Nickel-mediated allosteric manipulation of G-quadruplex DNAzyme for highly selective detection of histidine, Analytica Chimica Acta, 1008, (90), (2018).
  • , Artificial DNA Base Pairing Mediated by Diverse Metal Ions, Chemistry Letters, 10.1246/cl.160985, 46, 5, (622-633), (2017).
  • , Metal‐Mediated Base Pairs: From Characterization to Application, Chemistry – A European Journal, 23, 68, (17166-17178), (2017).
  • , Self-Assemblies Based on Metal-Mediated Artificial Nucleobase Pairing, Comprehensive Supramolecular Chemistry II, 10.1016/B978-0-12-409547-2.12556-9, (259-293), (2017).
  • , A metal-mediated base pair that discriminates between the canonical pyrimidine nucleobases, Chem. Sci., 10.1039/C6SC03482A, 8, 2, (1337-1343), (2017).
  • , Structure and properties of a copper-mediated nucleobase pair from density functional theory investigation, Inorganica Chimica Acta, 10.1016/j.ica.2016.03.047, 452, (194-198), (2016).
  • , Ferrocenyl-nucleobase complexes: Synthesis, chemistry and applications, Coordination Chemistry Reviews, 10.1016/j.ccr.2016.02.008, 317, (132-156), (2016).
  • , An electrochemical biosensor for sensitive detection of Hg 2+ based on exonuclease III-assisted target recycling and hybridization chain reaction amplification strategies , Analytical Methods, 10.1039/C5AY02793D, 8, 9, (2106-2111), (2016).
  • , Enantiospecific formation of a metal-mediated base pair inside a DNA duplex, Inorganica Chimica Acta, 10.1016/j.ica.2016.02.012, 452, (181-187), (2016).
  • , On the feasibility of recognition of nucleic acid sequences by metal-ion-carrying oligonucleotides, Inorganica Chimica Acta, 10.1016/j.ica.2016.01.025, 452, (43-49), (2016).
  • , Ultra-low Doping on Two-Dimensional Transition Metal Dichalcogenides using DNA Nanostructure Doped by a Combination of Lanthanide and Metal Ions, Scientific Reports, 6, 1, (2016).
  • , Label-free and dual-amplified electrochemical detection of Hg 2+ based on self-assembled DNA nanostructures and target-triggered exonuclease cleavage activity , New Journal of Chemistry, 10.1039/C6NJ00265J, 40, 8, (6686-6691), (2016).
  • , Das erweiterte genetische Alphabet, Angewandte Chemie, 127, 41, (12098-12113), (2015).
  • , A Highly Stabilizing Silver(I)‐Mediated Base Pair in Parallel‐Stranded DNA, Angewandte Chemie International Edition, 54, 12, (3603-3606), (2015).
  • , The Expanded Genetic Alphabet, Angewandte Chemie International Edition, 54, 41, (11930-11944), (2015).
  • , DNA with Metal‐Mediated Base Pairs, DNA in Supramolecular Chemistry and Nanotechnology, (52-64), (2017).
  • , DNA based multi-copper ions assembly using combined pyrazole and salen ligandosides, Chemical Science, 10.1039/C4SC01567C, 6, 1, (632-638), (2015).
  • , 4-(2′-Pyridyl)imidazole as an artificial nucleobase in highly stabilizing Ag(I)-mediated base pairs, JBIC Journal of Biological Inorganic Chemistry, 10.1007/s00775-015-1274-2, 20, 5, (895-903), (2015).
  • , G-quadruplex-based logic gates for Hg II and Ag I ions employing a luminescent iridium( iii ) complex and extension of metal-mediated base pairs by polymerase , Journal of Materials Chemistry B, 10.1039/C5TB00718F, 3, 24, (4780-4785), (2015).
  • , Metal-Triggered DNA Folding by Different Mechanisms, Chinese Journal of Chemical Physics, 10.1063/1674-0068/28/cjcp1503051, 28, 5, (630-638), (2015).
  • , Ein hochgradig stabilisierendes Silber(I)‐vermitteltes Basenpaar in paralleler DNA, Angewandte Chemie, 127, 12, (3674-3677), (2015).
  • , Theoretical Study of Silver-Ion-Mediated Base Pairs: The Case of C–Ag–C and C–Ag–A Systems, The Journal of Physical Chemistry A, 10.1021/jp5096739, 119, 21, (5153-5157), (2015).
  • , Metal‐Aided Construction of Unusual DNA Structural Motifs, DNA in Supramolecular Chemistry and Nanotechnology, (65-77), (2017).
  • , Bis(6-carboxypurine)-Cu 2+ : A Possibly Primitive Metal-Mediated Nucleobase Pair , Organic Letters, 10.1021/ol5018728, 16, 16, (4059-4061), (2014).
  • , The structure of metallo-DNA with consecutive thymine–HgII–thymine base pairs explains positive entropy for the metallo base pair formation, Nucleic Acids Research, 10.1093/nar/gkt1344, 42, 6, (4094-4099), (2013).
  • , n- and p-Type Doping Phenomenon by Artificial DNA and M-DNA on Two-Dimensional Transition Metal Dichalcogenides, ACS Nano, 8, 11, (11603), (2014).
  • , Regulated Incorporation of Two Different Metal Ions into Programmed Sites in a Duplex by DNA Polymerase Catalyzed Primer Extension, Angewandte Chemie International Edition, 53, 26, (6624-6627), (2014).
  • , Silver Arrays Inside DNA Duplexes Constructed from Silver(I)‐Mediated Pyrrolo‐dC–Pyrrolo‐dC Base Pairs, ChemPlusChem, 79, 7, (914-918), (2014).
  • , Regulated Incorporation of Two Different Metal Ions into Programmed Sites in a Duplex by DNA Polymerase Catalyzed Primer Extension, Angewandte Chemie, 126, 26, (6742-6745), (2014).
  • , (Non-) Covalently Modified DNA with Novel Functions, DNA in Supramolecular Chemistry and Nanotechnology, 10.1002/9781118696880.ch1, (1-77), (2015).
  • , 6-Substituted purines containing thienyl or furyl substituents as artificial nucleobases for metal-mediated base pairing, Dalton Transactions, 10.1039/c3dt51691a, 42, 45, (16080), (2013).
  • , Synthesis of 2,6-disubstituted pyridin-3-yl C-2′-deoxyribonucleosides through chemoselective transformations of bromo-chloropyridine C-nucleosides, Organic & Biomolecular Chemistry, 10.1039/c3ob40774h, 11, 28, (4702), (2013).
  • , Synthesis of nucleosides and dNTPs bearing oligopyridine ligands linked through an octadiyne tether, their incorporation into DNA and complexation with transition metal cations, Org. Biomol. Chem., 10.1039/C2OB26881G, 11, 1, (78-89), (2013).
  • , Metal-Ion Interactions with Nucleic Acids and Their Constituents, Comprehensive Inorganic Chemistry II, 10.1016/B978-0-08-097774-4.00317-X, (623-660), (2013).
  • , Artificial DNA Directed toward Synthetic Metallofoldamers, Metallofoldamers, (303-332), (2013).
  • , Conformation-Dependent Exonuclease III Activity Mediated by Metal Ions Reshuffling on Thymine-Rich DNA Duplexes for an Ultrasensitive Electrochemical Method for Hg 2+ Detection , Analytical Chemistry, 10.1021/ac400228q, 85, 9, (4586-4593), (2013).
  • , Ag + -Mediated DNA Base Pairing: Extraordinarily Stable Pyrrolo-dC–Pyrrolo-dC Pairs Binding Two Silver Ions , The Journal of Organic Chemistry, 10.1021/jo401109w, 78, 18, (9457-9463), (2013).
  • , Polymerase Recognition of a Watson–Crick‐Like Metal‐Mediated Base Pair: Purine‐2,6‐Dicarboxylate⋅Copper(II)⋅ Pyridine, ChemBioChem, 14, 18, (2403-2407), (2013).
  • , Artificial Genetic Sets Composed of Size‐Expanded Base Pairs, Angewandte Chemie International Edition, 52, 48, (12498-12508), (2013).
  • , Metal‐Locked DNA Three‐Way Junction, Angewandte Chemie International Edition, 52, 4, (1212-1216), (2012).
  • , Metal‐Locked DNA Three‐Way Junction, Angewandte Chemie, 125, 4, (1250-1254), (2012).
  • , Nucleic Acids With Metal‐Mediated Base Pairs and Their Applications, ChemPlusChem, 78, 1, (20-34), (2012).
  • , Künstliche genetische Systeme bestehend aus vergrößerten Basenpaaren, Angewandte Chemie, 125, 48, (12728-12739), (2013).
  • , Metal‐Ion‐Binding Analogs of Ribonucleosides: Preparation and Formation of Ternary Pd2+ and Hg2+ Complexes with Natural Pyrimidine Nucleosides, Helvetica Chimica Acta, 96, 9, (1658-1669), (2013).
  • , Mechanism of the hairpin folding transformation of thymine-cytosine-rich oligonucleotides induced by Hg(II) and Ag(I) ions, The European Physical Journal E, 10.1140/epje/i2013-13101-5, 36, 9, (2013).
  • , Metal Complexes as Alternative Base Pairs or Triplets in Natural and Synthetic Nucleic Acid Structures, Metallofoldamers, (333-377), (2013).
  • , Theoretical investigation on DNA/RNA base pairs mediated by copper, silver, and gold cations, Dalton Trans., 41, 6, (1816), (2012).
  • , Metal-Mediated DNA Base Pairing: Alternatives to Hydrogen-Bonded Watson–Crick Base Pairs, Accounts of Chemical Research, 10.1021/ar200313h, 45, 12, (2066-2076), (2012).
  • , Self‐Assembly of Nucleic Acids, Supramolecular Chemistry, (2012).
  • , Detection of silver(I) ions based on the controlled self-assembly of a perylene fluorescence probe, Analytical Biochemistry, 10.1016/j.ab.2012.07.024, 430, 1, (48-52), (2012).
  • , Synthesis of nucleoside mono- and triphosphates bearing oligopyridine ligands, their incorporation into DNA and complexation with transition metals, Org. Biomol. Chem., 10.1039/C1OB06359F, 10, 1, (49-55), (2012).
  • , Raman spectroscopic detection of the T-Hg II -T base pair and the ionic characteristics of mercury, Nucleic Acids Research, 10.1093/nar/gks208, 40, 12, (5766-5774), (2012).
  • , AgI Ion Mediated Formation of a C–A Mispair by DNA Polymerases, Angewandte Chemie International Edition, 51, 26, (6464-6466), (2012).
  • , AgI Ion Mediated Formation of a C–A Mispair by DNA Polymerases, Angewandte Chemie, 124, 26, (6570-6572), (2012).
  • , Theoretical Study on Reaction Scheme of Silver(I) Containing 5-Substituted Uracils Bridge Formation, The Journal of Physical Chemistry A, 115, 30, (8504), (2011).
  • , Pyrimidine–pyrimidine base pairs stabilized by silver( i ) ions , Chem. Commun., 10.1039/C0CC04091F, 47, 3, (941-943), (2011).
  • , Metal Binding to Ligand-Containing Peptide Nucleic Acids, Inorganic Chemistry, 50, 13, (6083), (2011).
  • , Triggered activity of a nicking endonuclease for mercuric(ii) ion-mediated duplex-like DNA cleavage, Chemical Communications, 10.1039/c1cc11858g, 47, 22, (6347), (2011).
  • , Contiguous Metal‐Mediated Base Pairs Comprising Two AgI Ions, Chemistry – A European Journal, 17, 23, (6533-6544), (2011).
  • , Infrared Spectrum of the Ag+–(Pyridine)2 Ionic Complex: Probing Interactions in Artificial Metal‐Mediated Base Pairing, ChemPhysChem, 12, 10, (1999-2008), (2011).
  • , A highly selective and sensitive on–off sensor for silver ions and cysteine by light scattering technique of DNA-functionalized gold nanoparticles, Chemical Communications, 47, 30, (8557), (2011).
  • , Solution structure of a DNA double helix with consecutive metal-mediated base pairs, Nature Chemistry, 10.1038/nchem.512, 2, 3, (229-234), (2010).
  • , Exotic DNAs Made of Nonnatural Bases and Natural Phosphodiester Bonds, Chemistry & Biodiversity, 7, 2, (259-282), (2010).
  • , Metal–base pairing in DNA, Coordination Chemistry Reviews, 10.1016/j.ccr.2010.04.014, 254, 19-20, (2391-2402), (2010).
  • , “Illusionary” Polymerase Activity Triggered by Metal Ions: Use for Molecular Logic‐Gate Operations, Angewandte Chemie International Edition, 49, 50, (9757-9760), (2010).
  • , Incorporation of Thymine Nucleotides by DNA Polymerases through T–HgII–T Base Pairing, Angewandte Chemie International Edition, 49, 37, (6516-6519), (2010).
  • , “Illusionary” Polymerase Activity Triggered by Metal Ions: Use for Molecular Logic‐Gate Operations, Angewandte Chemie, 122, 50, (9951-9954), (2010).
  • , A Reusable DNA Single‐Walled Carbon‐Nanotube‐Based Fluorescent Sensor for Highly Sensitive and Selective Detection of Ag+ and Cysteine in Aqueous Solutions, Chemistry – A European Journal, 16, 27, (8147-8154), (2010).
  • , Incorporation of Thymine Nucleotides by DNA Polymerases through T–HgII–T Base Pairing, Angewandte Chemie, 122, 37, (6666-6669), (2010).
  • , Silver(I) and Mercury(II) Complexes with 1‐Methyl‐1,2,4‐triazole as Models for Metal‐Mediated Base Pairs – Formation of Discrete Complexes in Solution vs. One‐ and Two‐Dimensional Coordination Polymers in the Solid State, European Journal of Inorganic Chemistry, 2010, 30, (4859-4864), (2010).
  • , DNA modified with metal complexes: Applications in the construction of higher order metal–DNA nanostructures, Coordination Chemistry Reviews, 10.1016/j.ccr.2010.02.026, 254, 19-20, (2403-2415), (2010).
  • , Bipyridine-modified oligonucleotides: Aggregation in the presence of metal ions, Inorganica Chimica Acta, 10.1016/j.ica.2007.12.005, 362, 3, (985-992), (2009).
  • , Structural and surface patterning studies of N3-metalated adenine–copper complexes involving metal–olefin interaction, Inorganica Chimica Acta, 10.1016/j.ica.2008.02.028, 362, 3, (855-860), (2009).
  • , Unnatural Nucleosides with Unusual Base Pairing Properties, Current Protocols in Nucleic Acid Chemistry, 37, 1, (1.4.1-1.4.32), (2009).
  • , Metal-mediated base pairing within the simplified nucleic acid GNA, Org. Biomol. Chem., 10.1039/B816142A, 7, 3, (476-482), (2009).
  • , Discrete Self‐Assembly of Iron(III) Ions inside Triple‐Stranded Artificial DNA, Angewandte Chemie International Edition, 48, 6, (1081-1084), (2008).
  • , Discrete Self‐Assembly of Iron(III) Ions inside Triple‐Stranded Artificial DNA, Angewandte Chemie, 121, 6, (1101-1104), (2008).
  • , Silver‐Ion‐Mediated DNAzyme Switch for the Ultrasensitive and Selective Colorimetric Detection of Aqueous Ag+ and Cysteine, Chemistry � A European Journal, 15, 14, (3347-3350), (2009).
  • , Engineering discrete stacks of aromatic molecules, Chemical Society Reviews, 10.1039/b901261n, 38, 6, (1714), (2009).
  • , Using in vitro transcription to construct scaffolds for one-dimensional arrays of mercuric ions, Journal of Inorganic Biochemistry, 10.1016/j.jinorgbio.2007.12.023, 102, 5-6, (1141-1151), (2008).
  • , Structure of Metallo-DNA Duplex, Seibutsu Butsuri, 10.2142/biophys.48.119, 48, 2, (119-124), (2008).
  • , An Alternative Nucleobase Code: Characterization of Purine–Purine DNA Double Helices Bearing Guanine–Isoguanine and Diaminopurine 7‐Deaza‐Xanthine Base Pairs, ChemBioChem, 9, 17, (2779-2783), (2008).
  • , Metal‐Ion‐Mediated Base Pairs in Nucleic Acids, European Journal of Inorganic Chemistry, 2008, 24, (3749-3763), (2008).
  • , Interaction of Pt(II) and Pd(II) complexes of terpyridine with 1-methylazoles: A combined experimental and density functional study, Inorganica Chimica Acta, 10.1016/j.ica.2006.07.031, 360, 1, (255-263), (2007).
  • , Metal‐Containing Nucleic Acid Structures Based on Synergetic Hydrogen and Coordination Bonding, Progress in Inorganic Chemistry, (545-612), (2008).
  • , A metallo base-pair incorporating a terpyridyl-like motif: bipyridyl-pyrimidinone·Ag(i)·4-pyridine, Chemical Communications, 42, (4401), (2007).
  • , An Artificial Base Pair, Mediated by Hydrogen Bonding and Metal‐Ion Binding, Angewandte Chemie International Edition, 46, 29, (5602-5604), (2007).
  • , Controlled Stacking of 10 Transition‐Metal Ions inside a DNA Duplex, Angewandte Chemie International Edition, 46, 1‐2, (250-253), (2006).
  • , Kontrolliertes Stapeln von zehn Übergangsmetallionen im Innern eines DNA‐Doppelstrangs, Angewandte Chemie, 119, 1‐2, (254-257), (2006).
  • , DNA–Metal Base Pairs, Angewandte Chemie International Edition, 46, 33, (6226-6236), (2007).
  • , Colorimetric Detection of Mercuric Ion (Hg2+) in Aqueous Media using DNA‐Functionalized Gold Nanoparticles, Angewandte Chemie International Edition, 46, 22, (4093-4096), (2007).
  • , Colorimetric Detection of Mercuric Ion (Hg2+) in Aqueous Media using DNA‐Functionalized Gold Nanoparticles, Angewandte Chemie, 119, 22, (4171-4174), (2007).
  • , Ein durch Wasserstoffbrücken und Metallionenbindung vermitteltes, künstliches Basenpaar, Angewandte Chemie, 119, 29, (5698-5701), (2007).
  • , DNA‐Metall‐Basenpaare, Angewandte Chemie, 119, 33, (6340-6350), (2007).
  • , Synthesis and Characterization of CuII Complexes with Amino Acid Substituted Di(2‐pyridyl)amine Ligands, European Journal of Inorganic Chemistry, 2007, 23, (3686-3694), (2007).
  • , Differential reactivity of α and β 2′-deoxyribonucleosides towards protonation and metalation, Journal of Inorganic Biochemistry, 10.1016/j.jinorgbio.2006.11.011, 101, 3, (470-476), (2007).
  • , Bioinspired organic chemistry, Annual Reports Section "B" (Organic Chemistry), 10.1039/b515108m, 102, (377), (2006).
  • , Bio-inspired Programmable Self-assembly on DNA Templates, Chemistry Letters, 10.1246/cl.2006.694, 35, 7, (694-699), (2006).
  • , Electron injection from the side of an M-DNA duplex, JBIC Journal of Biological Inorganic Chemistry, 10.1007/s00775-005-0052-y, 11, 1, (82-87), (2005).
  • , Electron transfer processes in DNA: mechanisms, biological relevance and applications in DNA analytics, Natural Product Reports, 10.1039/b504754b, 23, 6, (973), (2006).
  • , NMR Spectroscopic Study of a DNA Duplex with Mercury-Mediated T-T Base Pairs, Nucleosides, Nucleotides and Nucleic Acids, 10.1080/15257770600686154, 25, 4-6, (613-624), (2006).
  • , Metal–Salen‐Base‐Pair Complexes Inside DNA: Complexation Overrides Sequence Information, Chemistry – A European Journal, 12, 34, (8708-8718), (2006).
  • , Programmable self-assembly of metal ions inside artificial DNA duplexes, Nature Nanotechnology, 10.1038/nnano.2006.141, 1, 3, (190-194), (2006).
  • , Metal Ion Coordination to Azole Nucleosides, Chemistry – A European Journal, 11, 21, (6246-6253), (2005).
  • , A Highly DNA‐Duplex‐Stabilizing Metal–Salen Base Pair, Angewandte Chemie International Edition, 44, 44, (7204-7208), (2005).
  • , Ein hochgradig DNA‐Duplex‐stabilisierendes Metall‐Salen‐Basenpaar, Angewandte Chemie, 117, 44, (7370-7374), (2005).
  • , DNA Logic Gate Based on Metallo-Toehold Strand Displacement, PLoS ONE, 10.1371/journal.pone.0111650, 9, 11, (e111650), (2014).
  • , 6-Pyrazolylpurine as an Artificial Nucleobase for Metal-Mediated Base Pairing in DNA Duplexes, International Journal of Molecular Sciences, 10.3390/ijms17040554, 17, 4, (554), (2016).
  • , The Effects of Magnesium Ions on the Enzymatic Synthesis of Ligand-Bearing Artificial DNA by Template-Independent Polymerase, International Journal of Molecular Sciences, 10.3390/ijms17060906, 17, 6, (906), (2016).