Cited by 787Advanced biosensing and bioanalysis techniquesDNA and Nucleic Acid ChemistryMolecular Junctions and Nanostructures

Mechanisms for DNA Charge Transport

Open access
Genereux, Joseph C., Barton, Jacqueline K.·2010·Chemical Reviews

Abstract

DNA charge transport (CT) chemistry has received considerable attention by scientific researchers over the past 15 years since our first provocative publication on long range CT in a DNA assembly.1,2 This interest, shared by physicists, chemists and biologists, reflects the potential of DNA CT to provide a sensitive route for signaling, whether in the construction of nanoscale biosensors or as an enzymatic tool to detect damage in the genome. Research into DNA CT chemistry began as a quest to determine whether the DNA double helix, a macromolecular assembly in solution with π-stacked base pairs, might share conductive characteristics with π-stacked solids. Physicists carried out sophisticated experiments to measure the conductivity of DNA samples, but the means to connect discrete DNA assemblies into the devices to gauge conductivity varied, as did the conditions under which conductivities were determined. Chemists constructed DNA assemblies to measure hole and electron transport in solution using a variety of hole and electron donors. Here, too, DNA CT was seen to depend upon the connections, or coupling, between donors and the DNA base pair stack. Importantly, these experiments have resolved the debate over whether DNA CT is possible. Moreover these studies have shown that DNA CT, irrespective of the oxidant or reductant used to initiate the chemistry, can occur over long molecular distances but can be exquisitely sensitive to perturbations in the base pair stack. \n \nHere we review some of the critical characteristics of DNA charge transport chemistry, taking examples from a range of systems, and consider these characteristics in the context of their mechanistic implications. This review is not intended to be exhaustive but instead to be illustrative. For instance, we describe studies involving measurements in solution using pendant photooxidants to inject holes, conductivity studies with covalently modified assemblies, and electrochemical studies on DNA-modified electrodes. We do not focus in detail on the differences amongst these constructs but instead on their similarities. It is the similarity among these various systems that allows us to consider different mechanisms to describe DNA CT. Thus we review also the various mechanisms for DNA CT that have been put forth and attempt to reconcile these mechanistic proposals with the many disparate measurements of DNA CT. Certainly the debate among researchers has shifted from "is DNA CT possible?" to "how does it work?". This review intends to explore this latter question in detail.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1021/cr900228f

Cites

272 of 272 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • The distribution of Type I oxidative damage is modulated, with enhanced guanine specificity due to charge transfer within DNA.

    “The distribution of oxidatively generated damage involving Type I photosensitization has been shown to be modulated, leading to an enhanced guanine specificity by the occurrence of charge transfer within DNA (104,105).”

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Cites

Flagged first, then by citations

Research works printed but not linked: 65

  1. [9]Marcus RA, Sutin N. Biochim. Biophys. Acta. 1985;811:265. [Google Scholar]
  2. [10]Turro NJ, Barton JK. J. Biol. Inorg. Chem. 1998;3:201. [Google Scholar]
  3. [11]Endres RG, Cox DL, Singh RRP. Rev. Mod. Phys. 2004;76:195. [Google Scholar]
  4. [13]Müller K-H. Phys. Rev. B. 2006;73:045403. [Google Scholar]
  5. [22]Storm AJ, van Noort J, de Vries S, Dekker C. Appl. Phys. Lett. 2001;79:3881. [Google Scholar]
  6. [28]Meade TJ, Kayyem JF. Angew. Chem. Int. Ed. 1995;34:352. [Google Scholar]
  7. [29]Lyndon Pittman T, Miao W. J. Phys. Chem. C. 2008;112:16999. [Google Scholar]
  8. [30]Boon EM, Jackson NM, Wrightman MD, Kelley SO, Hill MG, Barton JK. J. Phys. Chem. B. 2003;107:11805. [Google Scholar]
  9. [36]Melvin T, Botchway S, Parker AW, O’Neill P. J. Chem. Soc., Chem. Commun. 1995;6:653. [Google Scholar]
  10. [44]Han Ha D, Nham H, Yoo K-H, So H-m, Lee H-Y, Kawai T. Chem. Phys. Lett. 2002;355:405. [Google Scholar]
  11. [45]Xu B, Zhang P, Li X, Tao N. Nano Lett. 2004;4:1105. [Google Scholar]
  12. [47]Xiao X, Xu B, Tao NJ. Nano Lett. 2004;4:267. [Google Scholar]
  13. [51]Williams TT, Odom DT, Barton JK. J. Am. Chem. Soc. 2000;122:9048. [Google Scholar]
  14. [67]Furrer E, Giese B. Helv. Chim. Acta. 2003;86:3623. [Google Scholar]
  15. [79]Nakatani K, Dohno C, Saito I. J. Am. Chem. Soc. 2000;122:5893. [Google Scholar]
  16. [83]Hunter WN, Brown T, Kneale G, Anand NN, Rabinovich D, Kennard O. J. Biol. Chem. 1987;262:9962. doi: 10.2210/pdb113d/pdb. [DOI] [PubMed] [Google Scholar] · DOI
  17. [89]Gasper SM, Schuster GB. J. Am. Chem. Soc. 1997;119:12762. [Google Scholar]
  18. [90]Hickerson RP, Prat F, Muller JG, Foote CS, Burrows CJ. J. Am. Chem. Soc. 1999;121:9423. [Google Scholar]
  19. [106]Nguyen KL, Steryo M, Kurbanyan K, Nowitzki KM, Butterfield SM, Ward SR, Stemp EDA. J. Am. Chem. Soc. 2000;122:3585. [Google Scholar]
  20. [118]Siriwong K, Voityuk AA, Newton MD, Rösch N. J. Phys. Chem. B. 2003;107:2595. [Google Scholar]
  21. [121]Kelley SO, Holmlin ER, Stemp EDA, Barton JK. J. Am. Chem. Soc. 1997;199:9861. [Google Scholar]
  22. [123]Lewis FD, Wu T, Liu X, Letsinger RL, Greenfield SR, Miller SE, Wasielewski MR. J. Am. Chem. Soc. 2000;122:2889. [Google Scholar]
  23. [129]Armitage B, Yu C, Devadoss C, Schuster GB. J. Am. Chem. Soc. 1994;116:9847. [Google Scholar]
  24. [130]Sanii L, Schuster GB. J. Am. Chem. Soc. 2000;122:11545. [Google Scholar]
  25. [131]Vicic DA, Odom DT, Núñez ME, Gianolio DA, McLaughlin LW, Barton JK. J. Am. Chem. Soc. 2000;122:8603. [Google Scholar]
  26. [132]Dotse AK, Boone EK, Schuster GB. J. Am. Chem. Soc. 2000;122:6825. [Google Scholar]
  27. [142]O’Neill MA, Barton JK. In: Topics in Current Chemistry. Schuster GB, editor. Vol. 237. Berlin: Springer; 2004. p. 67. [Google Scholar]
  28. [144]Seidel CAM, Shulz A, Sauer MHM. J. Phys. Chem. 1996;100:5541. [Google Scholar]
  29. [146]Sheu C, Foote CS. J. Am. Chem. Soc. 1995;117:6439. [Google Scholar]
  30. [147]Thorp HH. In: Topics in Current Chemistry. Schuster GB, editor. Vol. 237. Berlin: Springer; 2004. p. 159. [Google Scholar]
  31. [148]Johnston DH, Glasgow KC, Thorp HH. J. Am. Chem. Soc. 1995;117:8933. [Google Scholar]
  32. [150]Sistare MF, Codden SJ, Heimlich G, Thorp HH. J. Am. Chem. Soc. 2000;122:4742. [Google Scholar]
  33. [151]Lewis FD, Liu X, Hayes RT, Wasielewski MR. J. Am. Chem. Soc. 2000;122:12037. [Google Scholar]
  34. [152]Kurnikov IV, Tong GSM, Madrid M, Beratan DN. J. Phys. Chem. B. 2002;106:7. [Google Scholar]
  35. [153]Saito I, Takayama M, Sugiyama H, Nakatani K. J. Am. Chem. Soc. 1995;117:6406. [Google Scholar]
  36. [154]Sugiyama H, Saito I. J. Am. Chem. Soc. 1996;118:7063. [Google Scholar]
  37. [157]Saito I, Nakamura T, Nakatani K, Yoshioka Y, Yamaguchi K, Sugiyama H. J. Am. Chem. Soc. 1998;120:12686. [Google Scholar]
  38. [158]Voityuk AA, Jortner J, Bixon M, Rösch N. Chem. Phys. Lett. 2000;324:430. [Google Scholar]
  39. [161]Treadway CR, Hill MG, Barton JK. Chem. Phys. 2002;281:409. [Google Scholar]
  40. [166]Hartwich G, Caruana DJ, de Lumley-Woodyear T, Wu Y, Campbell CN, Heller A. J. Am. Chem. Soc. 1999;121:10803. [Google Scholar]
  41. [167]Lewis FD, Kalgutkar RS, Wu Y, Liu X, Liu J, Hayes RT, Miller SE, Wasielewski MR. J. Am. Chem. Soc. 2000;122:12346. [Google Scholar]
  42. [168]LeBard DN, Lilichenko M, Matyushov DV, Berlin YA, Ratner MA. J. Phys. Chem. B. 2003;107:14509. [Google Scholar]
  43. [180]Stemp EDA, Arkin M, Barton JK. J. Am. Chem. Soc. 1997;119:2921. [Google Scholar]
  44. [181]Schiemann O, Turro NJ, Barton JK. J. Phys. Chem. B. 2000;104:7214. [Google Scholar]
  45. [183]Shafirovich V, Dourandin A, Geacintov NE. J. Phys. Chem. B. 2001;105:8431. [Google Scholar]
  46. [185]Sobolewski AL, Domcke W. Phys. Chem. Chem. Phys. 2004;6:2763. [Google Scholar]
  47. [190]Brillouin L. In: Horizons in Biochemistry. Kasha M, Pullman B, editors. New York City: Academic Press; 1962. p. 295. 1962. [Google Scholar]
  48. [192]Baba Y, Sekiguchi T, Shimoyama I, Hirao N, Nath KG. Phys. Rev. B. 2006;74:205433. [Google Scholar]
  49. [199]Yonemoto EH, Saupe GB, Schmehl RH, Hubig SM, Riley RL, Iverson BL, Mallouk TE. J. Am. Chem. Soc. 1994;116:4786. [Google Scholar]
  50. [200]Berlin YA, Grozema FC, Siebbeles LDA, Ratner MA. J. Phys. Chem. C. 2008;112:10988. [Google Scholar]
  51. [204]Rösch N, Voityuk AAIn. In: Topics in Current Chemistry. Schuster GB, editor. Vol. 237. Berlin: Springer; 2004. p. 37. [Google Scholar]
  52. [210]Troisi A, Orlandi G. Chem. Phys. Lett. 2001;344:509. [Google Scholar]
  53. [211]Troisi A, Orlandi G. J. Phys. Chem. B. 2002;106:2093. [Google Scholar]
  54. [217]Renger T, Marcus RA. J. Phys. Chem. A. 2003;107:8404. [Google Scholar]
  55. [221]Hihath J, Chen F, Zhang P, Tao N. J. Phys. Condens. Matter. 2007;19:215202. [Google Scholar]
  56. [228]Jortner J, Bixon M, Voityuk AA, Rösch N. J. Phys. Chem. A. 2002;106:7599. [Google Scholar]
  57. [229]Sartor V, Boone E, Schuster GB. J. Phys. Chem. B. 2001;105:11057. [Google Scholar]
  58. [234]Bixon M, Jortner J. Chem. Phys. 2002;271:393. [Google Scholar]
  59. [235]Bixon M, Jortner J. Chem. Phys. 2006;326:252. [Google Scholar]
  60. [241]Hartwich G, Caruana DJ, de Lumley-Woodyear T, Wu Y, Campbell CN, Heller A. J. Am. Chem. Soc. 1999;121:10803. [Google Scholar]
  61. [250]Chang C-M, Castro Neto AH, Bishop AR. Chem. Phys. 2004;303:189. [Google Scholar]
  62. [264]Uskov DB, Burin AL. Phys. Rev. B. 2008;78:073106. [Google Scholar]
  63. [268]Friedman KA, Heller A. J. Phys. Chem. B. 2001;105:11859. [Google Scholar]
  64. [269]Heller A. Farad. Disc. 2000;116:1. [Google Scholar]
  65. [272]Steenken S, Jovanovic SV. J. Am. Chem. Soc. 1997;119:617. doi: 10.1021/ja003823x. [DOI] [PubMed] [Google Scholar] · DOI

Cited by

Sorted by citations

Authors
Genereux, J. C., & Barton, J. K.
Affiliations
California Institute of Technology (US)
Corresponding author
Barton, Jacqueline K.
Venue
Chemical Reviews
Published
2009-11-23
Volume
110
Issue
3
Pages
1642-1662
ISSN
  • 0009-2665 (ISSN-L)
  • 1520-6890
OpenAlex
W2091201245
Cited by
787
References
272
Citations by year
2026: 20 · 2025: 28 · 2024: 29 · 2023: 32 · 2022: 32 · 2021: 40 · 2020: 54 · 2019: 51 · 2018: 53 · 2017: 47 · 2016: 50 · 2015: 62 · 2014: 66 · 2013: 60 · 2012: 64
FWCI
4.00
Type
journal article
Language
en
Open access
Locations
  • Chemical Reviews (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
  • CaltechAUTHORS (California Institute of Technology) (submittedVersion)
Funders
National Institute of General Medical Sciences (GM49216, R01GM049216)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Advanced biosensing and bioanalysis techniques
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
  • Physical Sciences › Engineering › Electrical and Electronic Engineering › Molecular Junctions and Nanostructures
Keywords
DNA charge transport, charge transport mechanism, hole transport, electron transport, DNA-modified electrodes, DNA biosensor, DNA damage detection
MeSH terms
DNA, Electrons, Ions, Models, Molecular, Nucleic Acid Conformation, Oxidation-Reduction

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review