Voltammetric studies of the interaction of daunomycin anticancer drug with DNA and analytical applications

Chu, Xia; Shen, Guo‐Li; Jiang, Jian‐Hui; Kang, Tianfang; Xiong, Bin; Yu, Ru‐Qin

doi:10.1016/s0003-2670(98)00362-6

Cited by 109 publications

(48 citation statements)

References 15 publications

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“…22 The decrease in the peak current in the presence of DNA is due to a decrease in the apparent diffusion coefficient and the apparent concentration of the electroactive species. 5,16 Cyclic voltammetric titration of DNA with proflavine was carried out to determine the binding constant and the binding site size. A plot of Cb/Cf vs. CT for proflavine in the presence of 0.1 mM DNA is given in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…3 In addition to potential therapeutic applications, due to the electrochemical behavior of many drugs, DNA binding studies are anticipated to be useful in electroanalytical applications. [4][5][6][7] There are mainly three possible binding modes between DNA and small molecules: (1) An electrostatic interaction that extends the negatively charged phosphates outside the DNA double helix; (2) the interaction with grooves of DNA; and (3) an intercalation model in which the base pairs of DNA unwind to accommodate an intercalating agent. 8,9 Several techniques have been employed to study the binding of small molecules to DNA including, for example, viscometry, 10 UV-Vis spectroscopy, 11 isothermal calorimetric titration, 12 luminescence, 13 electrophoresis, 14 fluorescence 15 and electroanalytical methods.…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical and Spectroscopic Studies of the Interaction of Proflavine with DNA

Aslanoğlu

2006

ANAL. SCI.

135

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The interaction of proflavine with herring sperm DNA has been investigated by cyclic voltammetry and UV-Vis spectroscopy as well as viscosity measurements. Shifts in the peak potentials in cyclic voltammetry, spectral changes in UV absorption titration, an increase in viscosity of DNA and the results of the effect of ionic strength on the binding constant strongly support the intercalation of proflavine into the DNA double helix. The binding constant for the interaction between proflavine and DNA was K = 2.32 (±0.41) × 10 4 M -1 and the binding site size was 2.07 (±0.1) base pairs, estimated in voltammetric measurements. The value of the binding site size was determined to be closer to that expected for a planar intercalating agent. The standard Gibbs free-energy change is ca. -24.90 kJ/mol at 25˚C, indicating the spontaneity of the binding interaction. The binding constant determined by UV absorption measurements was K = 2.20 (±0.48) × 10 4 M -1 , which is very close to the value determined by cyclic voltammetry assuming that the binding equilibrium is static.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electrochemical and Spectroscopic Studies of the Interaction of Proflavine with DNA

Aslanoğlu

2006

ANAL. SCI.

135

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“…■ REFERENCES 36 fish sperm Tris 1.98 × 10 5 absorption/fluorescence 20,[26][27][28]32,34 calf-thymus phosphate 1.96 × 10 5 to 7.0 × 10 5 absorption 37 chicken blood McIlvain 1.8 × 10 5 cyclic voltammetry 45 calf-thymus phosphate 2.35 × 10 5 H 1 -NMR 46,47,51,52 4-and 6-mers deuterated phosphate 4.3 × 10 5 to 1.7 × 10 6 scanning force microscopy 53 pBluBacHis b ammonium acetate 1.2 × 10 5…”

Section: ■ Acknowledgmentsmentioning

confidence: 99%

Binding of the Anti-Cancer Drug Daunomycin to DNA Probed by Second Harmonic Generation

et al. 2013

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Second harmonic generation (SHG) was used to selectively probe DNA−drug interactions without the need for chemical labels or invasive detection methods. In particular, the binding constant of the anticancer drug daunomycin to a recognition triplet sequence in a 33-mer of double stranded DNA was determined. The SHG method, which is interface selective, probed the binding of daunomycin to DNA that was tethered to the surface of colloidal microparticles suspended in aqueous solution. Probing biomolecule coated colloids is expected to yield larger SH signals and provides experimental flexibility as compared to experiments performed at planar interfaces. The change in SHG intensity as daunomycin was added to the microparticle solution was fit to a Langmuir binding model, which yielded an equilibrium constant of 2.3 (±0.7) × 10 5 M −1 ; the corresponding Gibbs free energy change at 20°C is −7.2 ± 0.2 kcal/mol. Control experiments established that daunomycin preferentially binds to DNA at the recognition sequence. The equilibrium was found to be unaffected by the presence of free DNA in solution, and hyper-Rayleigh scattering from bulk molecules did not change with increasing daunomycin concentration. The extracted equilibrium constants are in agreement with the range of reported values found in the literature. ■ INTRODUCTIONThis work presents a sensitive method for determining equilibrium binding constants for biomolecular interactions in a label free and noninvasive way. The experiments used second harmonic generation (SHG) to probe the binding of a drug to DNA tethered to the surface of colloidal microparticles suspended in aqueous solution. Biomolecule coatings on nano-and microparticle surfaces have opened up a broad field of self-assembling superstructured materials; 1−7 some biomolecule coated particles have found applications in drug delivery systems and in vivo detection schemes. 8,9 The present work also builds on interface specific nonlinear optical experiments that have measured the electronic and vibrational spectra of DNA covalently bound to planar fused quartz surfaces immersed in aqueous media, 10−13 and recent work that tracked in real time the cleavage of DNA by the restriction enzyme EcoR1 and the subsequent rehybridization of DNA attached to colloidal polymer microparticles without labeled reporter molecules or invasive detection methods. 14 Using SHG to study biomolecular reactions, with one of the reactants attached to a colloidal interface, can yield larger signals than analogous experiments performed at planar interfaces due to the larger number of molecules that can be accommodated in the laser focus. Additionally, the number of particles in solution can be changed without changing the density of the DNA that is attached to the individual particles, allowing for flexibility in experimental design.The class of anthracycline chemotherapeutic drugs has long been studied due to their potent anticancer properties. 15−20 Daunomycin (structure given in Figure 1a) is a member of this class ...

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“…The interaction is expected to alter the DNA replication machinery that may lead to the death of cancerous cells. For such a system, where both forms of the drug interact with DNA, Scheme 3 can be applied [24]. Based upon the process discussed in Scheme 3, the following equation is obtained [25] …”

Section: Resultsmentioning

confidence: 99%

Electrochemical investigations of unexplored anthraquinones and their DNA binding

Shah¹,

Rauf²,

Ullah³

et al. 2013

J. Electrochem. Sci. Eng.

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Voltammetric studies of the interaction of daunomycin anticancer drug with DNA and analytical applications

Cited by 109 publications

References 15 publications

Electrochemical and Spectroscopic Studies of the Interaction of Proflavine with DNA

Electrochemical and Spectroscopic Studies of the Interaction of Proflavine with DNA

Binding of the Anti-Cancer Drug Daunomycin to DNA Probed by Second Harmonic Generation

Electrochemical investigations of unexplored anthraquinones and their DNA binding

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