Interaction of Doxorubicin with Polynucleotides. A Spectroscopic Study

Airoldi, Marta; Barone, Giampaolo; Gennaro, Giuseppe; Giuliani, Anna Maria; Giustini, Mauro

doi:10.1021/bi401687v

Cited by 68 publications

(70 citation statements)

References 56 publications

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“…This arrangement might be favoured by the high concentration of the salt (NaCl) screening the positive charge of the daunosamine ring; thus facilitating the self‐assembly of DX. For the sake of comparison, in Figure (black line), we report the CD spectrum of DX intercalated in the chiral double helix of the synthetic polynucleotide poly(dA–dT) ⋅ poly(dA–dT) . Interestingly, the spectra of DX inserted in the polynucleotide scaffold and the gel are very similar.…”

Section: Resultsmentioning

confidence: 97%

“…Green: [DX]=2.3×10 −5 m , l =1.00 cm; red: [DX]=10 m m , l =0.01 cm; blue: [DX]=10 m m and [NaCl]=0.75 m , l =0.01 cm; black: DX–polyAT system (from ref. ) reported for comparison. A picture of a typical DX gel is shown in the inset.…”

Section: Resultsmentioning

confidence: 99%

“…Indeed, the χ pol versus T curves are well accounted for by Equation , which describes the cooperative self‐assembly process, according to a nucleation–elongation mechanism:

true χ_{normalp normalo normall} = 1 - {normale}^{\frac{{Δ H}_{p o l}^{0}}{R} (() \frac{1}{T} - \frac{1}{T_{normalp normalo normall}})}

…”

Section: Resultsmentioning

confidence: 99%

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A Stereochemically Driven Supramolecular Polymerisation

Tasca

D’Abramo

Galantini

et al. 2018

Chemistry A European J

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Anthracyclines self-assemble in water into dimers. In the presence of sufficiently high salt (NaCl) concentrations, solutions of the antibiotic doxorubicin, but not those of the closely related molecules daunomycin and epirubicin, turn into gels barely compatible with the presence of small oligomers. The use of spectroscopic, scattering, imaging and computational techniques, allowed light to be shed on the self-assembly process that triggered doxorubicin gelification. A complex picture emerged, with doxorubicin molecules assembled into long, highly chiral, supramolecular aggregates made of hundreds of units, showing redshifted fluorescence spectra, very short fluorescence lifetimes and small-angle X-ray scattering profiles compatible with long cylinders. The involvement of specific chemical groups and the need for a specific stereochemistry of the monomers in the formation of a hydrogen-bond network to stabilise the supramolecular aggregates was supported by molecular dynamics calculations. A salt-induced, temperature-dependent, cooperative nucleation-elongation supramolecular polymerisation of the doxorubicin molecules is deduced.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

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A Stereochemically Driven Supramolecular Polymerisation

Tasca

D’Abramo

Galantini

et al. 2018

Chemistry A European J

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“…The amino group of doxorubicin in acidic media is protonated so that its interaction with the DNA helix partially suppresses stabilizing influence of the biopolymer due to shielding phosphate groups of the DNA backbone. The models of such DNA‐doxorubicin complexes have been discussed elsewhere on the base of spectral data . The influence of doxorubicin regularly increased with its concentration up to 0.1 mM.…”

Section: Resultsmentioning

confidence: 99%

Voltammetric Sensor with Replaceable Polyaniline‐DNA Layer for Doxorubicin Determination

et al. 2018

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New voltammetric DNA sensor has been developed on the base of glassy carbon electrode covered with electropolymerized polyaniline with entrapped native DNA saturated with Methylene blue. The thickness and redox properties of the coating are easily regulated by the number of potential cycles and pH of the solution. Doxorubicin competes with Methylene blue for DNA binding sites and suppresses the electron transfer within the layer. The measurement of the decay of the cathodic peak current made it possible to determine down to 0.01 nM doxorubicin. After that, DNA can be replaced by consecutive treatment of the biosensor with concentrated HCl and fresh DNA solution. Second involvement of DNA was confirmed by electrochemical impedance spectroscopy. The DNA sensor developed was tested on artificial samples mimicking ionic content of human serum and on commercial drug formulation containing doxorubicin.

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“…Doxo is an anthracycline antibiotic much used in cancer chemotherapies, especially to treat some types of leukemias, sarcomas, lymphomas, myelomas, neuroblastomas, and so forth. The interaction between doxo and disperse DNA has already been characterized in many aspects by using very different techniques such as optical tweezers, magnetic tweezers, microcalorimetry, viscosimetry, molecular modeling, atomic force microscopy (AFM), dynamic light scattering, crystallography, and various types of spectroscopies . Therefore, much information is known about the interaction when using disperse DNA molecules.…”

Section: Introductionmentioning

confidence: 99%

Doxorubicin hinders DNA condensation promoted by the protein bovine serum albumin (BSA)

et al. 2017

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In this work, we have studied the interaction between the anticancer drug doxorubicin (doxo) and condensed DNA, using optical tweezers. To perform this task, we use the protein bovine serum albumin (BSA) in the working buffer to mimic two key conditions present in the real intracellular environment: the condensed state of the DNA and the abundant presence of charged macromolecules in the surrounding medium. In particular, we have found that, when doxo is previously intercalated in disperse DNA, the drug hinders the DNA condensation process upon the addition of BSA in the buffer. On the other hand, when bare DNA is firstly condensed by BSA, doxo is capable to intercalate and to unfold the DNA condensates at relatively high concentrations. In addition, a specific interaction between BSA and doxo was verified, which significantly changes the chemical equilibrium of the DNA-doxo interaction. Finally, the presence of BSA in the buffer stabilizes the double-helix structure of the DNA-doxo complexes, preventing partial DNA denaturation induced by the stretching forces.

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Interaction of Doxorubicin with Polynucleotides. A Spectroscopic Study

Cited by 68 publications

References 56 publications

A Stereochemically Driven Supramolecular Polymerisation

A Stereochemically Driven Supramolecular Polymerisation

Voltammetric Sensor with Replaceable Polyaniline‐DNA Layer for Doxorubicin Determination

Doxorubicin hinders DNA condensation promoted by the protein bovine serum albumin (BSA)

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