Interactions between drugs and nucleic acids. Part 1. Dichroic studies of doxorubicin, daunorubicin, and their basic chromophore, quinizarin

Samorı̀, Bruno; Rossi, Andrea; Pellerano, I. Domini; Marconi, Giancarlo; Valentini, Luigi; Gioia, B.; Vigevani, A.

doi:10.1039/p29870001419

Cited by 17 publications

(24 citation statements)

References 8 publications

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“…The allowed low-energy (480 nm) and high-energy transitions (290 nm) are characteristic of πfπ* transitions polarized along the long and the short axis of the molecule, respectively. 4 The 290 nm short axis transition shows larger optical activity than the low-energy long axis transition at 480 nm. The bands around 320-350 nm are generally assigned to nfπ* transitions, without specific assignment to the three CdO functions present on the aglycone moiety.…”

Section: Discussionmentioning

confidence: 99%

“…In the absorption spectra two main bands of high intensity, around 290 and 480 nm, have been assigned to πfπ* transitions polarized along short (z) and long (y) axis of the molecule, respectively. 4 In the CD spectra, besides the bands cited above, two additional bands, observed around 320 and 350 nm, are generally assigned to nfπ* transitions, without specific indication of any of the three CdO functions present in the molecule.…”

Section: Introductionmentioning

confidence: 99%

“…2 Anthracyclines interact with numerous biological components such as DNA and membrane. Their electronic absorption and circular dichroism (CD) spectra have been found to be sensitive to their interactions with biological objects, [3][4][5][6][7] to the deprotonation of the anthracycline chromophore functions, and also to their binding to metal ions. 8 Thus, the complete assignment of the transitions observed should be very useful for various chemically and biochemically oriented studies.…”

Section: Introductionmentioning

confidence: 99%

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Circular Dichroism Studies on Anthracycline Antitumor Compounds. Relationship between the Molecular Structure and the Spectroscopic Data

Fiallo¹,

Tayeb²,

Suarato³

et al. 1998

Journal of Pharmaceutical Sciences

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The band assignment of the circular dichroism (CD) spectra of anthracyclines can provide us with the tools to study the interaction of these molecules with biomolecules, such as DNA and membranes, and also with metal ions. This paper reports the CD spectra of 17 anthracycline derivatives and the tentative assignment of the bands to specific electronic transitions. The deprotonation of some anthracyclines, such as doxorubicin, daunorubicin, and idarubicin, have been also studied in order to characterize the electronic transitions involved in the acid-base process. Our evidence suggests the following assignment. The position of the band assigned to pi-->pi transition, polarized along the short axis of the molecule ( approximately 290 nm), does not depend on the hydroxyl group at C(11) (presence and/or ionization state), whereas the position of the band assigned to the pi-->pi transition ( approximately 480 nm), polarized along the long axis, is strongly dependent on it. Concerning the n-->pi transitions, the bands at approximately 320 and approximately 350 nm have a strong contribution of the n-->pi C(12)=O transition and the n-->pi C(5)=O transition, respectively.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Circular Dichroism Studies on Anthracycline Antitumor Compounds. Relationship between the Molecular Structure and the Spectroscopic Data

Fiallo¹,

Tayeb²,

Suarato³

et al. 1998

Journal of Pharmaceutical Sciences

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“…The binding interactions of small molecules with DNA have been studied extensively with a variety of techniques, including fluorescence spectroscopy [9], dichroism spectroscopy [10], and X-ray diffraction [11]. With the development of high order analytical instruments and chemometric algorithms, it becomes easier to obtain and resolve multi-dimensional data from complex systems.…”

Section: Introductionmentioning

confidence: 99%

Competitive interaction of the antitumor drug daunorubicin and the fluorescence probe ethidium bromide with DNA as studied by resolving trilinear fluorescence data: the use of PARAFAC and its modification

et al. 2002

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The competitive interaction with DNA of daunorubicin (DR), being present in the clinical anti-tumor drug daunoblastina, and the fluorescence probe ethidium bromide (EB) has been studied by parallel-factor analysis (PARAFAC) and full-rank parallel-factor analysis (FRA-PARAFAC) of a fluorescence excitation-emission three-way data array. The PARAFAC algorithm can furnish stable resolution results for the data array studied, if the estimated number of chemical components is consistent with the real number. The FRA-PARAFAC algorithm is not sensitive to the estimated number of components of the fluorescence data array if the estimated number is not less than the real number. Both algorithms gave identical resolution for the three components concerned DR, EB, and the complex EB-DNA. Variations of the equilibrium concentrations of free DR, EB, and the complex EB-DNA were resolved by both algorithms. Experimental observation confirms the hypothesis that DR is an intercalator of DNA and that the binding interactions of DR and EB with DNA are a pair of parallel competitive intercalation reactions on same base sites of DNA. The method exemplified by this study provides a useful approach for studying competitive interactions of different drugs with DNA in the presence of interferents.

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“…Doxorubicin (Dox), and its interaction with DNA, is one of the most investigated anthracycline antitumoral drugs, by spectral (absorbance, fluorescence, circular dichroism) [31][32][33], electrochemical [34][35][36][37], and theoretical modeling [38,39].…”

Section: Interactions Of Au-gsh Ad Surface With Doxorubicinmentioning

confidence: 99%

Drug–GSH interaction on GSH–Au modified electrodes: A cyclic voltammetry and electrochemical impedance spectroscopy study

Latus

Enache

Volanschi

2011

Journal of Electroanalytical Chemistry

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Interactions between drugs and nucleic acids. Part 1. Dichroic studies of doxorubicin, daunorubicin, and their basic chromophore, quinizarin

Cited by 17 publications

References 8 publications

Circular Dichroism Studies on Anthracycline Antitumor Compounds. Relationship between the Molecular Structure and the Spectroscopic Data

Circular Dichroism Studies on Anthracycline Antitumor Compounds. Relationship between the Molecular Structure and the Spectroscopic Data

Competitive interaction of the antitumor drug daunorubicin and the fluorescence probe ethidium bromide with DNA as studied by resolving trilinear fluorescence data: the use of PARAFAC and its modification

Drug–GSH interaction on GSH–Au modified electrodes: A cyclic voltammetry and electrochemical impedance spectroscopy study

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