Semiconductivity of organic substances. Part 9.—Nucleic acid in the dry state

Eley, D. D.; Spivey, D. I.

doi:10.1039/tf9625800411

Cited by 439 publications

(300 citation statements)

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“…The hydrocarbon is usually suggested as the acceptor molecule and the work of Lovelock, Zlatkis and Becker (1962) has demonstrated the affinity of polycyclic hydrocarbons for thermally excited electrons. The effects of such an interaction could be transferred at least along certain localized regions of the helix as a result of the electronic structure of the stacked bases of the DNA molecule (Eley and Spivey, 1962) perhaps resulting in a decreased stability of the molecule.…”

Section: Discussionmentioning

confidence: 99%

The Interaction of Polycyclic Hydrocarbons and Nucleic Acids

Boyland¹,

Green²

1962

Br J Cancer

139

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THE present study is concerned with the discovery that the carcinogenic hydrocarbon benzo(a)pyrene (3,4-benzopyrene) is more soluble in aqueous DNA solutions than in water (Booth, Boyland, Manson and Wiltshire, 1951). A subsequent quantitative study of the solubility of various nitrogen-containing polycyclic carcinogens (dibenzocarbazoles and dibenzacridines) in aqueous DNA solutions revealed a similar reaction with DNA (Booth and Boyland, 1953). The binding to nucleic acids and polynucleotides of various planar dye molecules [in particular the acridine dyes, acridine orange (e.g. Steiner and Beers, 1959;Bradley and Felsenfeld, 1959), acriflavine (Oster, 1951; Heilweil and Van WVinkle, 1955) and proflavine (Peacocke and Skerrett, 1956;Lerman, 1961)] has been investigated in many laboratories and there has been a recent report of the interaction of purine derivatives themselves with nucleic acids (Ts'o, Helmkamp and Sander, 1962).Almost all the planar molecules for which binding to nucleic acids has been demonstrated, contain hetero-atoms or groups which could provide specific binding sites. The polycycic hydrocarbons have no such groups, so that the binding of these molecules to nucleic acids is of particular interest quite apart from the obvious implications for the carcinogenic action of certain types. The interaction of the carcinogenic benzo(a)pyrene and non-carcinogenic pyrene with nucleic acids has therefore been investigated in more detail. EXPERIMENTAL MaterialsThe polycyclic hydrocarbons were those described previously (Boyland and Green, 1962).The nucleic acids were provided bv Professor J. A. V. Butler and Dr. K. S. Kirby. They were in the form of the sodium salts and a 0 05 per cent solution of DNA in water had a sodium ion concentration of about 0.001, which would protect it against spontaneous denaturation. The solutions referred to as 0 05 per cent are based upon the weight of DNA as supplied-without correction for bound water. (The DNA sample used for most experiments had a nitrogen content of 12 per cent and phosphorus content of 6-95 per cent.) Glass-distilled water was used throughout this work.Estimation of solubility of hydrocarbons in nucleic acid solutions Excess solid hydrocarbon was shaken with the 0 05 per cent nucleic acid solution for 16 hr. (overnight) at room temperature (-... 220 C.) in light-shielded flasks.

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Section: Discussionmentioning

confidence: 99%

The Interaction of Polycyclic Hydrocarbons and Nucleic Acids

Boyland¹,

Green²

1962

Br J Cancer

139

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] The DNA π-stack is capable of mediating oxidative DNA damage over long molecular distances in a reaction that is sensitive to DNA sequence-dependent conformation and dynamics. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] A mixture of tunneling and hopping mechanisms has been proposed to account for this long-range chemistry, which is gated by dynamical variations within the stack.…”

Section: Introductionmentioning

confidence: 99%

Intercalative Stacking: A Critical Feature of DNA Charge-Transport Electrochemistry

et al. 2003

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In electrochemistry experiments on DNA-modified electrodes, features of the redox probe that determine efficient charge transport through DNA-modified surfaces have been explored using methylene blue (MB + ) and Ru(NH 3 ) 6 3+ as DNA-binding redox probes. The electrochemistry of these molecules is studied as a function of ionic strength to determine the necessity of tight binding to DNA and the number of electrons involved in the redox reaction; on the DNA surface, MB + displays 2e -/1H + electrochemistry (pH 7) and Ru(NH 3 ) 6 3+ displays 1e -electrochemistry. We examine also the effect of electrode surface passivation and the effect of the mode (intercalation or electrostatic) of MB + and Ru(NH 3 ) 6 3+ binding to DNA to highlight the importance of intercalation for reduction by a DNA-mediated charge-transport pathway. Furthermore, in experiments in which MB + is covalently linked to the DNA through a σ-bonded tether and the ionic strength is varied, it is demonstrated that intercalative stacking rather than covalent σ-bonding is essential for efficient reduction of MB + . The results presented here therefore establish that efficient charge transport to the DNA-binding moiety in DNA films requires intercalative stacking and is mediated by the DNA base pair array.

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“…4,8 From a nanoelectronics perspective, the DNA possesses ideal structural and molecular-recognition properties, and the understanding of the charge transport through DNA may result in the ambitious goal of self assembling nanodevices with a definite molecular architecture. 10 The hypothesis that double stranded DNA supports charge transport as a linear chain of overlapping orbitals located on the stacked base pairs, already advanced in the early sixties, 11 received first experimental boosts only recently via long-range electron transfer measurements. 12 As far as transport through DNA is concerned, the available experiments are still controversial mainly due to the complexity of the environment and the molecule itself ͑sequence variability, 13 thermal vibrations .…”

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confidence: 99%

Backbone-induced semiconducting behavior in shortDNAwires

et al. 2002

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We propose a model Hamiltonian for describing charge transport through short homogeneous double stranded DNA molecules. We show that the hybridization of the overlapping orbitals in the base-pair stack coupled to the backbone is sufficient to predict the existence of a gap in the nonequilibrium current-voltage characteristics with a minimal number of parameters. Our results are in a good agreement with the recent finding of semiconducting behavior in short poly(G)-poly(C) DNA oligomers. In particular, our model provides a correct description of the molecular resonances which determine the quasilinear part of the current out of the gap region. DOI: 10.1103/PhysRevB.65.241314 PACS number͑s͒: 72.80.Le, 05.60.Ϫk, 87.10.ϩe, 87.14.Gg The attempt to understand the mechanism of electron motion along DNA is the source of an intense debate in the biochemical and chemical physics communities. 1 Solving this problem is an essential step for the development of DNA-based molecular electronics. New insights to this issue are brought by recent breakthroughs in direct measurements through DNA molecules. 2-8 Transport measurements through nanostructured systems are potentially capable of addressing the basic issues of the conduction properties of molecular and supramolecular aggregates. The aftermath for the realization of molecular electronics devices is straightforward. 9 It is thus not surprising that DNA molecules became the subject of an intense study concerning their potency to carry an electric current, 2-7 and to provide a scaffold for the metal assembling of highly conductive nanowires. 4,8 From a nanoelectronics perspective, the DNA possesses ideal structural and molecular-recognition properties, and the understanding of the charge transport through DNA may result in the ambitious goal of self assembling nanodevices with a definite molecular architecture. 10 The hypothesis that double stranded DNA supports charge transport as a linear chain of overlapping orbitals located on the stacked base pairs, already advanced in the early sixties, 11 received first experimental boosts only recently via long-range electron transfer measurements. 12 As far as transport through DNA is concerned, the available experiments are still controversial mainly due to the complexity of the environment and the molecule itself ͑sequence variability, 13 thermal vibrations . . . ). Concerning theory, the most reliable procedure to tackle these systems would be the ab initio quantum chemistry approach. However, massive numerical costs complicate its use for realistic biological systems. 14 To our knowledge, at the present time, only few densityfunctional-theory ͑DFT͒ calculations for DNA molecules are available. 7,15 In a parallel development particular aspects of the DNA transport phenomenology have been explained as mediated by polarons, 16 solitons, 17 electrons or holes. 1,18 Such lack of a unifying theoretical scheme calls for reproducible and unambiguous experimental results that are still a great technological challenge.Recently, Porath ...

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Semiconductivity of organic substances. Part 9.—Nucleic acid in the dry state

Cited by 439 publications

References 0 publications

The Interaction of Polycyclic Hydrocarbons and Nucleic Acids

The Interaction of Polycyclic Hydrocarbons and Nucleic Acids

Intercalative Stacking: A Critical Feature of DNA Charge-Transport Electrochemistry

Backbone-induced semiconducting behavior in shortDNAwires

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