447 — Interaction of anthracycline antibiotics with biopolymers

Berg, Hermann; Horn, G.; Luthardt, U.; Ihn, W.

doi:10.1016/0302-4598(81)80025-6

Cited by 57 publications

(8 citation statements)

References 19 publications

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“…Since 1972 there is ample evidence demonstrated by X-ray crystallography [14] and other methods that adriamycin and analogous anthracycline compounds interact with dsDNA through intercalation [1,[15][16][17][18] and adriamycin actively accumulates in nuclear genome [19], but less is known as to whether it can directly oxidise ds-DNA after intercalation has occurred. In aqueous solution with low salt concentration B-DNA predominates and this is the structure into which intercalation occurs [3].…”

Section: Methodsmentioning

confidence: 99%

“…Adriamycin, Scheme 1, is an antibiotic of the family of anthracyclines with a wide spectrum of chemotherapeutic applications and anti-neoplasic action but that causes cardiotoxicity that ranges from a delayed and insidious cardiomyopathy to the amino function interacts with the dsDNA phosphate backbone and is fundamental in intercalation and binding affinities with dsDNA [15].…”

Section: Introductionmentioning

confidence: 99%

“…The experimental results presented here will give strong evidence that adriamycin can undergo oxidation or reduction after being intercalated into the DNA double helix. Polarographic techniques have been used previously to study the formation of the adriamycin-dsDNA complex in bulk solution [15]. Electrochemical activity for the adriamycin structurally related compound daunomycin intercalated with DNA was also observed using a carbon paste electrode [21].…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical detection of in situ adriamycin oxidative damage to DNA

Oliveira‐Brett

2002

Talanta

131

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Adriamycin intercalation and in situ interaction with double helix DNA was investigated using a voltammetric DNA-biosensor. Oxidation and reduction of adriamycin molecules intercalated in double helix DNA were investigated in order to understand the in vivo mechanism of action with this anti-neoplasic drug. The results showed that the interaction of adriamycin with DNA is potential-dependent causing contact between DNA guanine and adenine bases and the electrode surface such that their oxidation is easily detected. A mechanism for adriamycin reduction and oxidation in situ when intercalated in double helix DNA immobilised onto the glassy carbon electrode surface is presented and the formation of the mutagenic 8-oxoguanine explained.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Electrochemical detection of in situ adriamycin oxidative damage to DNA

Oliveira‐Brett

2002

Talanta

131

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“…Previously, polarographic behavior of DOX at dropping mercury electrode was studied [10,11]. It was shown that DOX is an electroactive substance [11] which is irreversibly adsorbed at different electrode surfaces (mercury [12] or carbon [13]).…”

Section: Introductionmentioning

confidence: 99%

Ex situ Voltammetry and Chronopotentiometry of Doxorubicin at a Pyrolytic Graphite Electrode: Redox and Catalytic Properties and Analytical Applications

2009

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Ex situ (adsorptive transfer stripping) electrochemical techniques in connection with basal-plane PGE have been applied to the study of redox and catalytic properties of doxorubicin (DOX). Cyclic and square-wave voltammetry and constant current chronopotentiometric stripping (CPS) analysis were used to follow reversible reduction of DOX quinone moiety around À 0.5 V and its coupling to catalytic oxygen reduction. CPS was for the first time used for sensitive ex situ determination of the DOX using the catalytic signal around À 0.5 V in the presence of oxygen, allowing detection of femtomole amounts of DOX. We show that specific interaction of DOX with double-stranded DNA can easily be monitored using the catalytic CPS signal.

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“…A survey of literature reveals that Adriamycin can promote oxidative damage to ds-DNA in cancerous cells, through the generation of reactive oxygen species. [8][9][10][11] Adriamycin and analogous anthracyclines interact with DNA through intercalation [12][13][14][15] and Adriamycin activity accumulates in nuclear genome. 16 Chemically modified electrodes (CME) as voltammetric biosensors 17 which accumulate analytes selectively and protect them from interference from other ions/electrochemical species have played a leading role in the analysis of biosynthetic polynucleotides containing adenine/or guanine residues, using species sensitive DPV method 18 As such, looking at the importance of the above fact, the work reported in the present paper is aimed at the fabrication of voltammetric Adriamycin biosensor on a GCFE and to study the interaction of Adriamycin (an anticancer drug) in situ with ds-DNA at its surface.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Drug Modified GCFE, for the Study of Its In‐Vivo Interaction Mechanism

Tiwari

Pitre

2008

J Chinese Chemical Soc

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An anticancer drug (Adriamycin) modified Glassy Carbon Fiber Electrode (GCFE) has been prepared to study its interaction with ds‐DNA. The redox reaction of Adriamycin molecules at the chemically modified GCFE helps in understanding the in‐vivo mechanism of action of this anti cancer drug. The modified electrode has been fabricated by the adsorption of Adriamycin on GCFE surface. The results of Differential Pulse Voltammetric (DPV) analysis in acetate buffer of pH 4.5 ± 0.1, showed that the interaction between DNA guanine and adenine bases and electrode surface, is easily detected. A suitable mechanism for the oxidation and reduction of Adriamycin in‐situ intercalated in ds‐DNA immobilized on to the GCFE surface has been explained. The drug‐DNA complex formation at GCFE surface has also been studied. The prepared modified electrode is of utmost relevance because the mechanism of interaction of DNA‐Adriamycin at charged interfaces is parallel to the in‐vivo DNA‐Adriamycin complex reaction, where the nucleic acid is in close contact with charged phospholipid membranes and proteins. The interaction studies of Adriamycin at modified GCFE using DPV method help in understanding the DNA‐Adriamycin reaction mechanism.

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447 — Interaction of anthracycline antibiotics with biopolymers

Cited by 57 publications

References 19 publications

Electrochemical detection of in situ adriamycin oxidative damage to DNA

Electrochemical detection of in situ adriamycin oxidative damage to DNA

Ex situ Voltammetry and Chronopotentiometry of Doxorubicin at a Pyrolytic Graphite Electrode: Redox and Catalytic Properties and Analytical Applications

Anticancer Drug Modified GCFE, for the Study of Its In‐Vivo Interaction Mechanism

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