Thermal stability of complexes of diaminoacridines with deoxyribonucleic acids of varying base content

Kleinwächter, V.; Balcarová, Zdeňka; Boháček, J.

doi:10.1016/0005-2787(69)90242-1

Cited by 37 publications

(7 citation statements)

References 22 publications

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“…1) and the decreased buoyant density (Fig. 8) support such a suggestion (15,16,19,29 It has been shown that the shift in the absorption maximum that occurs when AgNO3 is added to DNA is due to binding of the Ag+ to base-pairs.…”

mentioning

confidence: 73%

Silver Sulfadiazine: Interaction with Isolated Deoxyribonucleic Acid

Rosenkranz

1972

Antimicrob Agents Chemother

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Silver sulfadiazine (AgSu) was found to interact with isolated deoxyribonucleic acid (DNA) to form nondissociable complexes. These complexes differ in physical and chemical properties from those that are established when silver nitrate is added to DNA. The reaction between AgSu and DNA is visualized as occurring in two stages: (i) a weak and reversible interaction (intercalation) between DNA and the sulfadiazine moiety and (ii) a tight binding involving the silver atom. In the first stage, sodium sulfadiazine competes with AgSu for the DNA.Silver sulfadiazine (AgSu) was synthesized by Fox, who also established its effectiveness for the prevention and treatment of burn infections due to pseudomonads (8)(9)(10)28). Even though AgSu is a sulfonamide drug, its antibacterial activity is not a function of the sulfonamide moiety because its effectiveness is not reversed by p-aminobenzoic acid (10). Silver nitrate (AgNO3) reacts with deoxyribonucleic acid (DNA) in vitro (14, 31; see also 3 and 33); hence, it has been suggested (10) that AgSu reacts with the cellular DNA and that this forms the basis of its antibacterial action. It has been proposed further (10) that when AgSu reacts with the cellular DNA it dissociates and that only the silver ion becomes associated with DNA while the sulfadiazine portion is released. However, data on both the in vivo and in vitro effects of AgSu are scarce, and therefore an examination of its mode of action was undertaken. The present study shows that in vitro AgSu forms a complex with DNA which is unlike that formed when DNA is mixed with AgNO3; but it is also shown (25; (20), and bacteriophage DNA was isolated from Klebsiella phage E-1, currently under investigation in this laboratory. 3H-labeled DNA derived from chicken embryos was prepared as described previously (13). All DNA specimens were dissolved in 0.005 M NaNO3 and extensively dialyzed against 0.005 M NaNO3 to remove all traces of chloride (capable of reacting with AgNO3 to form AgCl).JSulfadiazines. AgSu (29.1% silver) and sodium sulfadiazine (NaSu) were generously provided by Marion Laboratories, Inc., Kansas City, Mo. Only freshly prepared solutions (in 0.005 M NaNO3) were used.Chemical analysis. The phosphorus content of DNA specimens was determined by the procedure of Fiske and Subbarow (7).Spectral analysis. The spectra of DNA solutions were taken with a Carey model 11 recording spectrophotometer, and the absorbance at selected wavelengths was checked with a Beckman DU-2 spectrophotometer.Centrifugal procedures. Sedimentation velocity studies were carried out on dilute solutions in 12-mm Kel-F centerpiece centrifuge cells. A Spinco model E analytical ultracentrifuge equipped with an ultraviolet optical system was operated at 50,740 rev/min, and pictures were taken at 2-min intervals. The photographs were traced with a Joyce-Loebl Mark III B microdensitometer, and sedimentation coefficients (S5".) and distributions of sedimentation co-

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mentioning

confidence: 73%

Silver Sulfadiazine: Interaction with Isolated Deoxyribonucleic Acid

Rosenkranz

1972

Antimicrob Agents Chemother

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“…When bound to DNA, AO fluoresces at different wavelengths, depending on the nature of the nucleic acid; green fluorescence occurs after binding to double-strand DNA, whereas red luminescence results from interaction with single-strand DNA. Thermal denaturation studies suggest that the overall stability of the DNA double helix is increased by AO binding [68]. However, local distortion and denaturation of double-stranded DNA are also generated, as evidenced by formaldehyde and diethylpyrocarbonate (DEPC) probing [69].…”

Section: Dna Ligand-mediated Unzippingmentioning

confidence: 99%

DNA‐Destabilizing Agents as an Alternative Approach for Targeting DNA: Mechanisms of Action and Cellular Consequences

Lenglet

David-Cordonnier

2010

Journal of Nucleic Acids

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DNA targeting drugs represent a large proportion of the actual anticancer drug pharmacopeia, both in terms of drug brands and prescription volumes. Small DNA-interacting molecules share the ability of certain proteins to change the DNA helix's overall organization and geometrical orientation via tilt, roll, twist, slip, and flip effects. In this ocean of DNA-interacting compounds, most stabilize both DNA strands and very few display helix-destabilizing properties. These types of DNA-destabilizing effect are observed with certain mono- or bis-intercalators and DNA alkylating agents (some of which have been or are being developed as cancer drugs). The formation of locally destabilized DNA portions could interfere with protein/DNA recognition and potentially affect several crucial cellular processes, such as DNA repair, replication, and transcription. The present paper describes the molecular basis of DNA destabilization, the cellular impact on protein recognition, and DNA repair processes and the latter's relationships with antitumour efficacy.

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“…dye, which dissociates cooperatively a t temperatures characterized by the values T , (see Figure 6 and Table 111) indicates that, compared to the aqueous medium, higher fraction of proflavine is bound by the weaker binding process II.20s23 It was found earlier that the weakly bound dye contributes significantly less to the stabilization of the DNA double helix than the strongly bound dye. 23 The reduction of the stabilization effect in the presence of organic solvents can thus be attributed to the decrease of the total amount of the bound dye and the relative decrease of the proportion of proflavine bound by the stronger process I.…”

Section: Denaturation Of the Dna-dye Complexes In The Presence Of Orgmentioning

confidence: 99%

Effect of organic solvents on the properties of the complexes of DNA with proflavine and similar compounds

Löber¹,

Schütz²,

Kleinwächter

1972

Biopolymers

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SynopsisIn order to obtain information on the binding forces involved in the formation of the complex proflavine-DNA by the stronger process I, the stability of the complexes was investigated in the presence of various organic solvents, methanol, ethanol, n-propanol, isopropanol, formamide, dimethyl sulfoxide, p-dioxane, glycerol, and ethylene glycol. Quantitative data on binding in terms of K l n and r were obtained by means of absorption and fluorescence spectra, as well as by a thermal denaturation technique.The effectiveness of the solvents increases with their hydrocarbon content, but can hardly be related to their dielectric constant. The complex formation is effectively suppressed by organic solvent concentrations, in which DNA still preserves its double-helical conformation. These results demonstrate the importance of hydrophobic forces in the formation of the complex proflavine-DNA in aqueous solution.The similarity in spectroscopic properties of proflavine bound to DNA by process I and the same dye dissolved in an organic solvent make it possible to interpret the observed red shift of the long-wavelength absorption peak as being due to the interaction of the dye molecules with the less polar environment.The same behavior was found for other dyes capable of intercalation like purified trypaflavine, phenosafranine and ethidium bromide. However, intercalation is not a necessary condition, as it was shown in the case of pinacyanol, which binds only a t the surface of DNA.All organic solvents used decrease the binding ability of the dye.

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Thermal stability of complexes of diaminoacridines with deoxyribonucleic acids of varying base content

Cited by 37 publications

References 22 publications

Silver Sulfadiazine: Interaction with Isolated Deoxyribonucleic Acid

Silver Sulfadiazine: Interaction with Isolated Deoxyribonucleic Acid

DNA‐Destabilizing Agents as an Alternative Approach for Targeting DNA: Mechanisms of Action and Cellular Consequences

Effect of organic solvents on the properties of the complexes of DNA with proflavine and similar compounds

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