Selective Photocleavage of DNA by Anthraquinone Derivatives:  Targeting the Single-Strand Region of Hairpin Structures

Henderson, Paul; Armitage, Bruce A.; Schuster, Gary B.

doi:10.1021/bi972419g

Cited by 30 publications

(25 citation statements)

References 44 publications

(64 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Outersphere guanine oxidation is therefore likely to compete with hydrogen abstraction in DNA photoreactions. Numerous studies have shown that one-electron oxidation of guanine eventually leads to piperidine-labile cleavages specifically at guanine nucleotides (10,(22)(23)(24)(25)(26)(27). In the evaluation of the effects of secondary structure on the piperidine enhancement, the side reaction involving guanine oxidation must therefore be considered.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Effects of Secondary Structure on DNA and RNA Cleavage by Diplatinum(II)

1998

View full text Add to dashboard Cite

The photochemistry of Pt2(pop)44- with nucleic acids has been studied using radiolabeled oligomers of DNA and RNA and high-resolution electrophoresis (pop is P2O5H22-). Photolysis of Pt2(pop)44- with duplex DNA produces an even cleavage ladder and relatively little enhancement of cleavage upon treatment with piperidine. In contrast, the cleavage pattern is far less regular with single-stranded DNA, and there is a large enhancement in cleavage upon treatment with piperidine. Accordingly, photolysis of Pt2(pop)44- with the DNA hairpin 5'-d[ATCCTATTTATAGGAT] produces a much larger piperidine enhancement at the loop and end nucleotides than in the stem. There is an additional piperidine enhancement that occurs selectively at guanine residues either in RNA or in DNA at low Mg2+ concentrations that is attributed to outer-sphere electron transfer on the basis of the known excited-state redox potentials of Pt2(pop)44- and the expected oxidative chemistry of guanine. The extent of guanine oxidation is higher compared to the extent of sugar oxidation at low Mg2+ concentrations, which can be attributed to a shallower distance dependence for electron transfer compared to that for atom transfer. The effects of Mg2+ and piperidine or aniline treatment were examined on stem-loop structures of DNA and RNA and gave partial images of the expected secondary structures.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Recently, Schuster and co-workers have reported that an anthraquinone derivative selectively targets the loop region of a DNA hairpin (25). In this case, NMR studies show a binding interaction of the anthraquinone with the loop bases.…”

Section: Discussionmentioning

confidence: 99%

Effects of Secondary Structure on DNA and RNA Cleavage by Diplatinum(II)

1998

View full text Add to dashboard Cite

show abstract

“…In addition to quinones, hydroxy (53,65,67,93), carboxy (53), hydroxymethyl and formyl-PAHs for methyl substituted PAHs (70) are also detected among the photolysis products. Quinones are known reactive oxygen species sensitizers (28,31,147,148). On the other hand, quinones are relatively stable compounds against photo-oxidation.…”

Section: Perspectivesmentioning

confidence: 99%

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

2002

Journal of Environmental Science and Health, Part C

341

252

View full text Add to dashboard Cite

“…The study of electron-transfer reactions in DNA is an important problem both from a fundamental materials science perspective [1][2][3][4][5][6][7][8][9][10] and because of its biological consequences. [11][12][13][14][15] As such electron transfers are fast chemical processes, they are usually initiated by short laser-pulse excitation of sensitizers such as phenothiazonium dyes, [16,17] anthraquinones [18,19] or metal complexes. [20][21][22][23][24] The study of compounds intercalated into DNA is especially appropriate for theoretical treatment as the relative orientation of the electron donor and acceptor is well defined.…”

Section: Introductionmentioning

confidence: 99%

Photooxidation of Guanine by a Ruthenium Dipyridophenazine Complex Intercalated in a Double‐Stranded Polynucleotide Monitored Directly by Picosecond Visible and Infrared Transient Absorption Spectroscopy

Elias

Creely

Doorley

et al. 2007

Chemistry A European J

100

View full text Add to dashboard Cite

Transient species formed by photoexcitation (400 nm) of [Ru(dppz)(tap)2]2+ (1) (dppz = dipyrido[3,2-a:2',3'-c]phenazine; tap=1,4,5,8-tetraazaphenanthrene) in aqueous solution and when intercalated into a double-stranded synthetic polynucleotide, [poly(dG-dC)]2, have been observed on a picosecond timescale by both visible transient absorption (allowing monitoring of the metal complex intermediates) and transient infrared (IR) absorption spectroscopy (allowing direct study of the DNA nucleobases). By contrast with its behavior when free in aqueous solution, excitation of 1 when bound to [poly(dG-dC)]2 causes a strong increase in absorbance at 515 nm due to formation of the reduced complex [Ru(dppz)(tap)2]+ (rate constant=(2.0+/-0.2) x 10(9) s(-1)). The subsequent reformation of 1 proceeds with a rate constant of (1.1+/-0.2) x 10(8) s(-1). When the process is carried out in D2O, the rates of formation and removal of [Ru(dppz)(tap)2]+ are reduced (rate constants (1.5+/-0.3) x 10(9) and (0.7+/-0.2) x 10(8) s(-1) respectively) consistent with proton-coupled electron transfer processes. Picosecond transient IR measurements in the 1540-1720 cm(-1) region in D2O solution confirm that the reduction of 1 intercalated into [poly(dG-dC)]2 is accompanied by bleaching of IR ground-state bands of guanine (1690 cm(-1)) and cytosine (1656 cm(-1)), each with similar rate constants.

show abstract

Selective Photocleavage of DNA by Anthraquinone Derivatives: Targeting the Single-Strand Region of Hairpin Structures

Cited by 30 publications

References 44 publications

Effects of Secondary Structure on DNA and RNA Cleavage by Diplatinum(II)

Effects of Secondary Structure on DNA and RNA Cleavage by Diplatinum(II)

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

Photooxidation of Guanine by a Ruthenium Dipyridophenazine Complex Intercalated in a Double‐Stranded Polynucleotide Monitored Directly by Picosecond Visible and Infrared Transient Absorption Spectroscopy

Contact Info

Product

Resources

About