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Original Article

Identification and quantification of isoguanosine in humans and mice

, , , & ORCID Icon
Pages 225-232 | Received 14 Sep 2018, Accepted 16 Feb 2019, Published online: 19 Mar 2019

References

  • Fischer E. Synthese des hypoxanthins, xanthins, adenins und guanins. Ber Dtsch Chem Ges. 1897;30:2226–2254.
  • Cherbuliez E, Bernhard K. Recherches sur la graine de croton. I. Sur le crotonoside (2-oxy-6-amino-purine-d-riboside). Helv Chim Acta. 1932;15:464–471.
  • Purrmann R. Über die Flügelpigmente der Schmetterlinge. VII. Justus Liebigs. Ann Chem. 1940;544:182–191.
  • Fuhrman FA, Fuhrman GJ, Nachman RJ, et al. Isoguanosine: isolation from an animal. Science. 1981;212:557–558.
  • Cheng Q, Gu J, Compaan KR, et al. Isoguanine formation from adenine. Chemistry. 2012;18:4877–4886.
  • Kamiya H, Kasai H. Formation of 2-hydroxydeoxyadenosine triphosphate, an oxidatively damaged nucleotide, and its incorporation by DNA polymerases. J Biol Chem. 1995;270:19446–19450.
  • Johnson SC, Sherrill CB, Marshall DJ, et al. A third base pair for the polymerase chain reaction: inserting isoC and isoG. Nucleic Acids Res. 2004;32:1937–1941.
  • Fujikawa K, Kamiya H, Yakushiji H, et al. Human MTH1 protein hydrolyzes the oxidized ribonucleotide, 2-hydroxy-ATP. Nucleic Acids Res. 2001;29:449–454.
  • Kamiya H, Suzuki A, Kawai K, et al. Effects of 8-hydroxy-GTP and 2-hydroxy-ATP on in vitro transcription. Free Radic Biol Med. 2007;43:837–843.
  • Kamiya H. Mutagenicity of oxidized DNA precursors in living cells: roles of nucleotide pool sanitization and DNA repair enzymes, and translesion synthesis DNA polymerases. Mutat Res. 2010;703:32–36.
  • Ewing PL, Schlenk F, Emerson GA. Comparison of smooth muscle effects of crotonoside (isoguanosine) and adenosine. J Pharmacol Exp Ther. 1949;97:379–383.
  • Hagen C. Effect of purine analogues on IMP-pyrophosphorylase. Biochim Biophys Acta. 1973;293:105–110.
  • Kim JH, Lee SJ, Han YB, et al. Isolation of isoguanosine from Croton tiglium and its antitumor activity. Arch Pharm Res. 1994;17:115–118.
  • Jaworski A, Kwiatkowski JS, Lesyng B. Why isoguanine and isocytosine are not the components of the genetic code. Int J Quantum Chem. 1986;12:209–216.
  • Seela F, Wei C, Melenewski A. Oligonucleotides containing consecutive 2′-deoxy-isoguanosine residues: synthesis, parallel duplex formation and identification of a d(T4iG4T4) tetraplex. Nucleosides Nucleotides Nucleic Acids. 1997;16:1523–1527.
  • Mori T, Hori Y, Dizdaroglu M. DNA base damage generated in vivo in hepatic chromatin of mice upon whole body gamma-irradiation. Int J Radiat Biol. 1993;64:645–650.
  • Olinski R, Zastawny T, Budzbon J, et al. DNA base modifications in chromatin of human cancerous tissues. FEBS Lett. 1992;309:193–198.
  • Kamiya H, Ueda T, Ohgi T, et al. Misincorporation of dAMP opposite 2-hydroxyadenine, an oxidative form of adenine. Nucleic Acids Res. 1995;23:761–766.
  • Kamiya H. Biological and pharmaceutical aspects of nucleic acids chemistry. Biol Pharm Bull. 2004;27:475–479.
  • Kamiya H, Kasai H. Substitution and deletion mutations induced by 2-hydroxyadenine in Escherichia coli: effects of sequence contexts in leading and lagging strands. Nucleic Acids Res. 1997;25:304–310.
  • Kasai H. Chemistry-based studies on oxidative DNA damage: formation, repair, and mutagenesis. Free Radic Biol Med. 2002;33:450–456.
  • Frelon S, Douki T, Cadet J. Radical oxidation of the adenine moiety of nucleoside and DNA: 2-hydroxy-2′-deoxyadenosine is a minor decomposition product. Free Radic Res. 2002;36:499–508.
  • Cadet J, Douki T, Ravanat J-L. Artifacts associated with the measurement of oxidized DNA bases. Environ Health Perspect. 1997;105:1034–1039.
  • Cadet J, D'Ham C, Douki T, et al. Facts and artifacts in the measurement of oxidative base damage to DNA. Free Radic Res. 1998;29:541–550.
  • Cadet J, Douki T, Ravanat J-L, et al. Measurement of oxidatively generated base damage to nucleic acids in cells: facts and artifacts. Bioanal Rev. 2012;4:55–74.
  • Murata-Kamiya N, Kamiya H, Muraoka M, et al. Comparison of oxidation products from DNA components by gamma-irradiation and Fenton-type reactions. J Radiat Res. 1997;38:121–131.
  • Hofer T, Seo AY, Prudencio M, et al. A method to determine RNA and DNA oxidation simultaneously by HPLC-ECD: greater RNA than DNA oxidation in rat liver after doxorubicin administration. Biol Chem. 2006;387:103–111.
  • Weimann A, Belling D, Poulsen HE. Quantification of 8-oxo-guanine and guanine as the nucleobase, nucleoside and deoxynucleoside forms in human urine by high-performance liquid chromatography–electrospray tandem mass spectrometry. Nucleic Acids Res. 2002;30:e7.
  • EU Commission Decision 2002/657/EC of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off J Eur Commun. 2002;L 221:8–36.
  • Weimann A, Simonsen AH, Poulsen HE. Measurement of 8-oxo-7,8-dihydro-2′-deoxyguanosine and 8-oxo-7,8-dihydro-guanosine in cerebrospinal fluid by ultra performance liquid chromatography–tandem mass spectrometry. J Chromatogr B. 2018;1073:110–117.
  • Cadet J, Wagner JR. Oxidatively generated base damage to cellular DNA by hydroxyl radical and one-electron oxidants: similarities and differences. Arch Biochem Biophys. 2014;557:47–54.
  • Weimann A, Broedbaek K, Henriksen T, et al. Assays for urinary biomarkers of oxidatively damaged nucleic acids. Free Radic Res. 2012;46:531–540.
  • Havelund JF, Giessing AMB, Hansen T, et al. Identification of 5-hydroxycytidine at position 2501 concludes characterization of modified nucleosides in E. coli 23S rRNA. J Mol Biol. 2011;411:529–536.
  • Jobert L, Skjeldam HK, Dalhus B, et al. The human base excision repair enzyme SMUG1 directly interacts with DKC1 and contributes to RNA quality control. Mol Cell. 2013;49:339–345.
  • The RNA Modification Database. The RNA Institute, College of Arts and Sciences, State University of New York at Albany.
  • Calabretta A, Küpfer PA, Leumann CJ. The effect of RNA base lesions on mRNA translation. Nucleic Acids Res. 2015;43:4713–4720.

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