Acridizinium Salts as a Novel Class of DNA-binding and Site-selective DNA-photodamaging Chromophores¶

Ihmels, Heiko; Faulhaber, Katja; Sturm, Christian; Bringmann, Gerhard; Messer, Kim; Gabellini, Nadia; Vedaldi, Daniela; Viola, Giampietro

doi:10.1562/0031-8655(2001)074<0505:asaanc>2.0.co;2

Cited by 33 publications

(40 citation statements)

References 26 publications

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“…All measurements were carried out in ETN buffer (TRIS 10 mM, EDTA 1 mM and NaCl, 10 mM) at pH = 7.0 and 25°C. The titration experiments were performed according to published procedures [9][10][11][12] and the data, plotted as Scatchard plot, 14 were analyzed by the method of McGhee and von Hippel 15 to obtain the intrinsic binding constant (K i ) and the binding site size (n). Flow linear dichroism.…”

Section: Methodsmentioning

confidence: 99%

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DNA-binding and DNA-photocleavaging properties of 12a,14a-diazoniapentaphene

Viola¹,

Ihmels²,

Kraußer³

et al. 2004

Arkivoc

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Section: Methodsmentioning

confidence: 99%

“…The determination and interpretation of the data was performed according to a previous publication. 9,11,12 Fluorescence contact energy transfer. Contact-energy transfer from DNA bases to the associated dye was determined from the excitation spectra of the DNA-dye complex from 230-330 nm with an interval of 1 nm.…”

Section: Methodsmentioning

confidence: 99%

DNA-binding and DNA-photocleavaging properties of 12a,14a-diazoniapentaphene

Viola¹,

Ihmels²,

Kraußer³

et al. 2004

Arkivoc

Self Cite

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“…All measurements were carried out in ETN buffer (tris(hydroxymethyl)aminomethane (Tris; 10 mM), ethylenediaminetetraacetate (EDTA; 1 mM), NaCl to adjust the ionic strength to the desired values) at pH 7.0 and 25 8C. The titration experiments were performed according to published procedures [17] and the data, plotted as a Scatchard plot, [21] were analyzed by the method of McGhee and von Hippel. [20] to obtain the intrinsic binding constant (K i ) and the binding site size (n).…”

Section: Methodsmentioning

confidence: 99%

“…The determination and interpretation of the data was performed according to a previous publication. [17] Fluorescence contact energy transfer: Contact energy transfer from DNA bases to the associated dye was determined from the excitation spectra of the DNA ± dye complex from 230 to 330 nm with an interval of 1 nm. Fluorescence was monitored at l em 452 nm.…”

Section: Methodsmentioning

confidence: 99%

Indolo[2,3-b]-Quinolizinium Bromide: An Efficient Intercalator with DNA-Photodamaging Properties

et al. 2002

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The associative interactions of indolo[2,3-b]-quinolizinium bromide with DNA and its DNA photocleavage properties were studied in detail. Absorption and emission spectroscopy, linear dichroism, and energy-transfer measurements indicate that the indoloquinolizinium binds to DNA primarily by intercalation, with a preference for GC base pairs. In agreement with this data, the results of primer extension analysis indicate that photocleavage occurrs prevalently at the GC nucleotides. Molecular modeling studies confirm that intercalative stacking between adjacent base pairs is energetically favorable. However, it is also observed that the location of the dye in the minor groove of the DNA is energetically even more favorable. Upon UVA irradiation, the indoloquinolizinium causes single-strand cleavage with an efficiency that varies with the dye-DNA ratio. This observation is rationalized in terms of more efficient photocleavage by the externally bound dye compared with the intercalated one. The kinetics of strand degradation under aerobic and anaerobic conditions suggest that a Type I reaction occurs, that is, radical-mediated DNA damage.

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“…Aliquots (10 µL) were taken after various irradiation intervals and kept on ice. Primer extension was performed with [γ-33 P]-labeled M13 reverse primer and the pUC18 as the template, and the DNA synthesis was carried out by the Taq polymerase as described previously (18,19). Amplified DNA fragments were separated electrophoretically on a 6% acrylamide, 50% urea gel.…”

Section: Dna Strand Breaksmentioning

confidence: 99%

Photosensitization of DNA Strand Breaks by Three Phenothiazine Derivatives

Viola

Latterini

Vedaldi

et al. 2003

Chem. Res. Toxicol.

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The interaction and the photosensitizing activity of three phenothiazine derivatives, fluphenazine hydrochloride (FP), thioridazine hydrochloride (TR), and perphenazine (PP), toward DNA were studied. Evidences obtained from various spectroscopic studies such as fluorimetric and linear dichroism measurements indicate that these derivatives bind to the DNA at least in two ways: intercalation and external stacking on the DNA helix, depending on their relative concentrations. Irradiation of supercoiled plasmid DNA in the presence of these phenothiazines leads to single strand breaks. The DNA photocleavage appears to be due to externally bound molecules rather than to those intercalated. The highest photocleavage activity was observed with PP and TR whereas FP was less efficient. The efficiency of the photocleavage in aerated and deaerated solutions does not change thus indicating that an involvement of singlet oxygen can be excluded. Primer extension analysis of plasmid DNA irradiated in the presence of phenothiazines indicates that photocleavage of DNA occurs predominantly at Gua and Cyt residues. Laser flash experiments carried out in the presence of 2'-deoxyguanosine 5'-monophosphate reveal an efficient electron transfer between the nucleotide and the radical cations produced by photoionization of the phenothiazines. In the presence of DNA, an electron transfer process takes place within the laser pulse from the lowest singlet state of phenothiazines to the DNA bases; the time-resolved measurements showed that the back-electron transfer is a negligible decay pathway for the charged species.

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Acridizinium Salts as a Novel Class of DNA-binding and Site-selective DNA-photodamaging Chromophores¶

Cited by 33 publications

References 26 publications

DNA-binding and DNA-photocleavaging properties of 12a,14a-diazoniapentaphene

DNA-binding and DNA-photocleavaging properties of 12a,14a-diazoniapentaphene

Indolo[2,3-b]-Quinolizinium Bromide: An Efficient Intercalator with DNA-Photodamaging Properties

Photosensitization of DNA Strand Breaks by Three Phenothiazine Derivatives

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