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Number of results

Journal

2015 | 13 | 1 |

Article title

The influence of the phosphorothioate diester bond on the DNA oxidation process

Content

Title variants

Languages of publication

EN

Abstracts

EN

Publisher

Journal

Year

Volume

13

Issue

1

Physical description

Dates

received
2 - 6 - 2015
online
20 - 10 - 2015
accepted
24 - 8 - 2015

Contributors

References

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  • [6] Misiszek, R., Crean C., Joffe A., Geacintov N.E., Shafirovich V., Oxidative DNA damage associated with combination of guanine and superoxide radicals and repair mechanisms via radical trapping, J. Biol. Chem., 2004, 297, 32106-32115.
  • [7] Wagneknecht, H-A. (Eds.), Charge transfer in DNA: from mechanism to application, Wiley-VCH Verlag GmbH & Co. KgaA, 2005.
  • [8] Rokhlenko Y., Geacintiv N.E., Shafirovich N., Lifetimes and reaction pathway of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions, J. Am. Chem. Soc., 2012, 134, 4955-4962.
  • [9] Rokhlenko, Y., Cadet J., Geacintov N.E., Shafirovich V., Mechanistic aspects of hydration of guanine radical cation in DNA, J. Am. Chem. Soc., 2014, 136, 5956-5962.
  • [10] Genereux, J.C., Barton J.K., Mechanisms for DNA charge transport, Chem. Rev., 2010, 110, 1642-1662.[WoS]
  • [11] Chworos, A., Coppel, Y., Dubey, I., Pratviel, G., Meunier B., Guanine oxidation: NMR characterization of a dehydro-guanidinohydantoin residue generated by a 2e-oxidation of d(GpT), J. Am. Chem. Soc., 2001, 123, 5867-5877.
  • [12] Chworos, A., Seguy, Ch., Pratviel, G., Meunier B., Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide, Chem. Res. Toxicol., 2002, 15, 1643-1651.
  • [13] Karwowski, B., Dupeyrat, F., Bardet, M., Ravanat, J-L., Krajewski, P., Cadet J., Nuclear magnetic resonance studies of the 4R and 4S diastereomers of spiroiminodihydantoin 2′-deoxyribonucleosides: absolute configuration and conformational features, Chem. Res. Toxicol., 2006, 19, 1357-1365.[Crossref]
  • [14] McCullough, A.K., Dodson, M.L., Lloyd R.S., Initiation of base excision repair: glycosylase mechanisms and structures, Ann. Rev. Biochem., 1999, 68, 255-285.
  • [15] Sancar, A., Lindsey-Boltz, L.A., Unsal-Kacmaz, K., Linn S., Molecular mechanisms of mammalian DNA repair and the DNA damage checkpoints, Ann. Rev. Biochem., 2004, 73, 39-85.
  • [16] Limon-Pacheco, J., Gonsebatt M.E., The role of antioxidants and antioxidant-related enzymes in protective responses to environmentally induced oxidative stress, Mutat Res., 2009, 31, 137-147.[WoS]
  • [17] Wang, L., Chen, S., Xu, T., Taghizadeh, K., Wishnok, J.S., Zhou, X., et al., Phosphorothioation of DNA in bacteria by dnd genes, Nat. Chem. Biol., 2007, 3, 709–710.
  • [18] Kanvah, S., Schuster G.B., Oxidative damage to DNA: inhibition of guanine damage, Pure Appl. Chem., 2006, 78, 2297-2304.
  • [19] Adhikary, A., Kumar, A., Palmer, B.J., Todd, A.D., Sevilla M.D., Formation of S–Cl phosphorothioate adduct radicals in dsDNA S-oligomers: hole transfer to guanine vs disulfide anion radical formation, J. Am. Chem. Soc., 2013, 135, 12827-12838.[WoS]
  • [20] Gasper, M.S., Shuster G.B., Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: the effect of gaps and traps on long-range radical cation migration, J. Am. Chem. Soc., 1997, 119, 12762-12771.
  • [21] Karwowski, B., The influence of the terminal phosphorothioate diester bond on the DNA oxidation process. An experimental and theoretical approach, Molecules, 2015, 20, 12400-12411.[Crossref][WoS]
  • [22] Breslin, D.T., Schuster G.B., Anthraquinone photonucleases: mechanisms for GG-selective and nonselective cleavage of double-stranded DNA, J. Am. Chem., Soc., 1996, 118, 2311-2319.
  • [23] Quantity One 1-D analysis software, version 4.6.6., Bio-Rad Laboratories, CA, USA, 2000.
  • [24] Brinboim H.C., Kanabus-Kaminska M., The production of DNA strand brakes in human leukocytes by superoxide anion my involve a metabolic process, Proc. Natl. Acad. Sci. USA, 1985, 82, 6820-6824.
  • [25] Barnett, N.R., Cleceland, Ch.L., Landman, U., Boone, E., Kanvah, S., Schuster G.B., Effect of base sequence and hydration on the electronic and hole transport properties of duplex DNA: theory and experiment, J. Phys. Chem. A., 2003, 107, 3525-3537.
  • [26] Sinha, N.D., Jung, K.E., Analysis and purification of synthetic nucleic acids using HPLC, Curr. Protoc. Nucleic Acid Chem., 2015, 61:10.5.1-10.5.39.
  • [27] Kanvah, S., Schuster G.B., One-electron oxidation of DNA: thymine versus guanine reactivity, Org. Biomol. Chem., 2010, 8, 1340-1343.[Crossref][WoS]
  • [28] Meggers, E., Michel-Beyerle, M.E., Giese B., Sequence dependent long range hole transport in DNA, J. Am. Chem. Soc., 1998, 120, 12950-12955.
  • [29] Lewis, F.D., Zuo, X., Hayes R.T., Wasilewski M.R., Dynamics and inter- and intra-strand hole transport in DNA hairpins, J. Am. Chem. Soc., 2002, 124, 4568-4569.
  • [30] Joseph, J., Schuster G.B., Emergent functionality of nucleobase radical cations in duplex DNA: prediction of reactivity using qualitative potential energy landscapes, J. Am. Chem. Soc., 2006, 128, 6070-6074.
  • [31] Ghosh. A., Joy, A., Schuster, G.B., Douki, T., Cadet J., Selectiveone-electronoxidation of duplex DNA oligomers: reaction at thymines, Org. Biomol. Chem., 2008, 6, 916-928.[Crossref]
  • [32] Liu, Ch-S., Hernandez, R., Schuster G.B., Mechanism for radical cation transport in duplex DNA oligonucleotides, J. Am. Chem. Soc., 2004, 126, 2877-2884.
  • [33] Senthilkumar K., Grozema F.C., Guerra C.F., Bickelhaupt F.M., Siebbeles L.D.A., Mapping the sites for selective oxidation of guanines in DNA, J. Am. Chem. Soc., 2003, 125, 13658-13659.
  • [34] Giese, B., Amaudrut, J., Kohler, A., Spormann, M., Wessely S., Direct observation of hole transfer through DNA by hopping between adenine bases and by tunnelling, Nature, 2001, 412, 318-320.
  • [35] Schuster G.B., Landman U., The mechanism of long-distance radical cation transport in duplex DNA: ion-gated hopping of polaron-like distortions, Top Curr. Chem., 2004, 236, 139-161.
  • [36] Hong S., Greenberg M.M., Efficient DNA interstrand cross-link formation from a nucleotide radical, J. Am. Chem. Soc., 2005, 127, 3692-3693.
  • [37] Karwowski, B. The influence of phosphorothioate on charge migration in double and single stranded DNA. The theoretical approach, Phys. Chem. Chem. Phys., 2015, 17, 21507-21516.[WoS]
  • [38] Xie, X., Liang, J., Pu, T., Xu, F., Yao, F., Yang, Y., et al., Phosphorothioate DNA as an antioxidant in bacteria, Nuc. Acid. Res., 2012, 40, 9115-9124.
  • [39] Wu, L., White, D.E., Ye, C., Vogt, F.G., Terfloth, G.J., Matsuhashi H., Desulfurization of phosphorothioate oligonucleotides via the sulfur-by-oxygen replacement induced by the hydroxyl radical during negative electrospray ionization mass spectrometry, J. Mass. Spectrom., 2012, 47, 836-844. [WoS]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_1515_chem-2015-0136
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