Visible absorption and proton nuclear magnetic resonance studies on the self-association of doxorubicin in aqueous solution.

Hayakawa, Eiji; Furuya, Kunitoshi; Ueno, Hideo; Kuroda, Tokuyuki; Moriyama, Masuo; Kondô, Akira

doi:10.1248/cpb.39.1009

Cited by 23 publications

(11 citation statements)

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“…Support for the suggestion of decreased stacking between adjacent chromophores in the gels is also provided by published variable‐temperature 1 H NMR spectroscopy studies of DX gels . The DX dimer formation is accompanied by an upfield shift of the aromatic ring protons NMR signals, which is attributed to increased shielding caused by stacking . However, it was shown that going from a DX dimer solution to the corresponding gel by decreasing the temperature caused a deshielding of the aromatic protons, similar to deshielding observed in the transition from di‐ to monomer obtained by increasing the temperature .…”

Section: Discussionsupporting

confidence: 52%

“…[19] The DX dimer formation is accompanied by an upfield shift of the aromatic ring protons NMR signals, which is attributed to increaseds hielding caused by stacking. [4,41] However,i tw as shown that going from aD Xd imer solution to the corresponding gel by decreasing the temperature caused ad eshielding of the aromatic protons, similar to deshielding observed in the transition from di-to monomer obtained by increasing the temperature. [19] Thus, it appears that both the polymerisation process and dimer-to-monomer transition are accompanied by ar educed degree of stacking.…”

Section: Discussionmentioning

confidence: 66%

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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: Discussionsupporting

confidence: 52%

Section: Discussionmentioning

confidence: 66%

A Stereochemically Driven Supramolecular Polymerisation

Tasca

D’Abramo

Galantini

et al. 2018

Chemistry A European J

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“…It has been reported (Agrawal et al, 2009;Anand et al, 2012;Fulop et al, 2013;Hayakawa et al, 1991;Li et al, 1998;Porumb, 1978;Rizzo et al, 1989) that Dox tends to self-assemble in aqueous solutions forming dimers or higher order oligomers. The extent of agglomeration is highly sensitive to concentration of drug macromolecules, acidity of solution, and presence of additives (Anand et al, 2012;Hayakawa et al, 1991;Porumb, 1978). Self-assembling of Dox molecules leads to the changes in the relative intensities of absorption peaks in the visible region of spectra ( Figure 9).…”

Section: Isotherms Of Doxorubicin Adsorptionmentioning

confidence: 98%

Adsorption of antitumor antibiotic doxorubicin on MCM-41-type silica surface

Roik

Belyakova

Dziazko

2016

Adsorption Science & Technology

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The aim of this study was to evaluate the adsorption behavior of doxorubicin on MCM-41 silica, which was synthesized by templated sol-gel method, as a function of contact time, pH of solution, and drug equilibrium concentration. Experimental kinetic curves of adsorption were compared with theoretical models of Lagergren and Ho-McKay for pseudo-first-and pseudo-second-order processes. Equilibrium adsorption of doxorubicin was analyzed by Langmuir, Freundlich, RedlichPeterson, and Brunauer-Emmet-Teller isotherm models. These results can be the basis for direct modification of MCM-41-type silicas sorption activity to drugs.

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“…Intercalators such as ethidium bromide, proflavine, and acridine orange, 4,5 and end-stacking ligands like the camptothecins 6 have all been shown to aggregate. Equally, minor groove binders berberine 7 and Hoechst 33258 (H33258), 8,9 combined intercalator/ minor groove binders such as daunomycin, 10 related doxorubicin 11 and methylene blue 12 have been reported to aggregate in aqueous solution. Ligand self-association almost certainly has in vivo consequences but more immediately this phenomenon presents a clear difficulty when undertaking biophysical studies of ligand binding.…”

Section: Introductionmentioning

confidence: 99%