Sensitizing DNA Towards Low-Energy Electrons with 2-Fluoroadenine

被引:45
作者
Rackwitz, Jenny [1 ]
Kopyra, Janina [2 ]
Dabkowska, Iwona [3 ]
Ebel, Kenny [1 ]
Rankovic, MiloS Lj. [4 ]
Milosavljevic, Aleksandar R. [4 ,5 ]
Bald, Ilko [1 ,6 ]
机构
[1] Univ Potsdam, Inst Chem Phys Chem, Karl Liebknecht Str 24-25, D-14476 Potsdam, Germany
[2] Siedlce Univ, Fac Sci, 3 Maja 54, PL-08110 Siedlce, Poland
[3] Univ Gdansk, Dept Chem, PL-80952 Gdansk, Poland
[4] Univ Belgrade, Inst Phys Belgrade, Pregrevica 118, Belgrade 11080, Serbia
[5] SOLEIL, BP48, F-91192 Gif Sur Yvette, France
[6] BAM Fed Inst Mat Res & Testing, Dept Analyt Chem & Reference Mat 1, Richard Willstatter Str 11, D-12489 Berlin, Germany
关键词
ab initio calculations; dissociative electron attachment; DNA origami; DNA radiation damage; fludarabine; PLATINUM CHEMOTHERAPEUTIC DRUGS; STRAND BREAKS; CROSS-SECTIONS; NEGATIVE-IONS; PLASMID DNA; SINGLE; ATTACHMENT; RADIATION; NUCLEOBASES; DECOMPOSITION;
D O I
10.1002/anie.201603464
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Fluoroadenine ((2F)A) is a therapeutic agent, which is suggested for application in cancer radiotherapy. The molecular mechanism of DNA radiation damage can be ascribed to a significant extent to the action of low-energy (<20 eV) electrons (LEEs), which damage DNA by dissociative electron attachment. LEE induced reactions in (2F)A are characterized both isolated in the gas phase and in the condensed phase when it is incorporated into DNA. Information about negative ion resonances and anion-mediated fragmentation reactions is combined with an absolute quantification of DNA strand breaks in (2F)A-containing oligonucleotides upon irradiation with LEEs. The incorporation of (2F)A into DNA results in an enhanced strand breakage. The strand-break cross sections are clearly energy dependent, whereas the strand-break enhancements by (2F)A at 5.5, 10, and 15 eV are very similar. Thus, (2F)A can be considered an effective radiosensitizer operative at a wide range of electron energies.
引用
收藏
页码:10248 / 10252
页数:5
相关论文
共 46 条
  • [11] Electron attachment to chlorouracil: A comparison between 6-ClU and 5-ClU
    Denifl, S
    Matejcik, S
    Ptasinska, S
    Gstir, B
    Probst, M
    Scheier, P
    Illenberger, E
    Mark, TD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2004, 120 (02) : 704 - 709
  • [12] Denifl S., 2007, ANGEW CHEM, V119, P5331
  • [13] Influence of functional groups on the site-selective dissociation of adenine upon low-energy electron attachment
    Denifl, Stephan
    Sulzer, Philipp
    Huber, Dieter
    Zappa, Fabio
    Probst, Michael
    Maerk, Tilmann D.
    Scheier, Paul
    Injan, Natcha
    Limtrakul, Jumras
    Abouaf, Robert
    Dunet, Henri
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5238 - 5241
  • [14] FLUDARABINE IMPROVES THE THERAPEUTIC RATIO OF RADIOTHERAPY IN MOUSE-TUMORS AFTER SINGLE-DOSE IRRADIATION
    GREGOIRE, V
    HUNTER, N
    BROCK, WA
    MILAS, L
    PLUNKETT, W
    HITTELMAN, WN
    [J]. INTERNATIONAL JOURNAL OF RADIATION ONCOLOGY BIOLOGY PHYSICS, 1994, 30 (02): : 363 - 371
  • [15] Hotop H., 2003, ADV ATOMIC MOL OPTIC, V49
  • [16] High resolution dissociative electron attachment to gas phase adenine
    Huber, D.
    Beikircher, M.
    Denifl, S.
    Zappa, F.
    Matejcik, S.
    Bacher, A.
    Grill, V.
    Maerk, T. D.
    Scheier, P.
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2006, 125 (08)
  • [17] Single, double, and multiple double strand breaks induced in DNA by 3-100 eV electrons
    Huels, MA
    Boudaïffa, B
    Cloutier, P
    Hunting, D
    Sanche, L
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) : 4467 - 4477
  • [18] Ultrafast energy transfer between water molecules
    Jahnke, T.
    Sann, H.
    Havermeier, T.
    Kreidi, K.
    Stuck, C.
    Meckel, M.
    Schoeffler, M.
    Neumann, N.
    Wallauer, R.
    Voss, S.
    Czasch, A.
    Jagutzki, O.
    Malakzadeh, A.
    Afaneh, F.
    Weber, Th.
    Schmidt-Boecking, H.
    Doerner, R.
    [J]. NATURE PHYSICS, 2010, 6 (02) : 139 - 142
  • [19] Sequence dependence of electron-induced DNA strand breakage revealed by DNA nanoarrays
    Keller, Adrian
    Rackwitz, Jenny
    Cauet, Emilie
    Lievin, Jacques
    Koerzdoerfer, Thomas
    Rotaru, Alexandru
    Gothelf, Kurt V.
    Besenbacher, Flemming
    Bald, Ilko
    [J]. SCIENTIFIC REPORTS, 2014, 4
  • [20] Electron-induced damage of biotin studied in the gas phase and in the condensed phase at a single-molecule level
    Keller, Adrian
    Kopyra, Janina
    Gothelf, Kurt V.
    Bald, Ilko
    [J]. NEW JOURNAL OF PHYSICS, 2013, 15