DNA-binding study of anthraquinone derivatives using Chemometrics methods

Gholivand, Mohammad Bagher; Kashanian, Soheila; Peyman, Hossein; Roshanfekr, Hamideh

doi:10.1016/j.ejmech.2011.03.034

Cited by 58 publications

(24 citation statements)

References 68 publications

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“…Based on the proven efficacy of anthracyclines and related compounds in antitumor application, their molecular motifs may serve as a good platform for structural modification to enhance potency in other types of cytotoxic agents. A unique feature of anthracyclines is the presence of a 1,4-dihydroxyanthraquinone moiety that may play a key role both in the DNA binding and cell or tissue bioavailability [14–16]. Considering the importance of the 1,4-dihydroxyanthraquinone moiety in anticancer drugs and biologically active natural products [17–19], the combination of a 1,4-dihydroxyanthraquinone structure with an N-mustard moiety could lead to novel compounds possessing potent anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of novel hydroxyanthraquinone nitrogen mustard derivatives as potential anticancer agents via a bioisostere approach

Zhao

Jin

et al. 2015

European Journal of Medicinal Chemistry

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A series of hydroxyanthraquinones having an alkylating N-mustard pharmacophore at 1′-position were synthesized via a bioisostere approach to evaluate their cytotoxicity against four tumor cell lines (MDA-MB-231, HeLa, MCF-7 and A549). These compounds displayed significant in vitro cytotoxicity against MDA-MB-231 and MCF-7 cells, reflecting the excellent selectivity for the human breast cancer. Among them, compound 5k was the most cytotoxic with IC50 value of 0.263 nM and is more potent than DXR (IC50 = 0.294 nM) in inhibiting the growth of MCF-7 cells. The excellent cytotoxicity and good selectivity of compound 5k suggest that it could be a promising lead for further design and development of anticancer agents, especially for breast cancer.

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of novel hydroxyanthraquinone nitrogen mustard derivatives as potential anticancer agents via a bioisostere approach

Zhao

Jin

et al. 2015

European Journal of Medicinal Chemistry

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“…The presence of the nonzero peak current for the mediated oxygen reduction at high concentrations of DNA is also likely a result of the QZ adsorption. Even given this lower sensitivity toward DNA, this current electrochemical method exhibits significantly lower levels of detection than obtainable by comparable UV-visible-based methods (25,28). This situation arises predominantly because of the ability to study far lower concentrations of QZ in this work.…”

Section: Resultsmentioning

confidence: 84%

The electrochemistry of quinizarin revealed through its mediated reduction of oxygen

Batchelor‐McAuley

Dimov

Aldous

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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After 35 years the hunt for improved anthracycline antibiotics is unabated but has yet to achieve the levels of clinical success desired. Electrochemical techniques provide a large amount of kinetic and thermodynamic information, but the use of such procedures is hindered by issues of sensitivity and selectivity. This work demonstrates how by harnessing the mechanism of catalytic reduction of oxygen by the quinone functionality present within the anthracycline structure it is possible to study the reactive moiety in nanomolar concentration. This methodology allows electrochemical investigation of the intercalation of quinizarin into DNA and, in particular, the quinone oxidation and degradation mechanism. The reversible reduction of the quinizarin, which in the presence of oxygen leads to the formation of reactive oxygen species, is found to occur at −0.535 V (vs. SCE) pH 6.84 and the irreversible oxidation leading to the molecules degradation occurs at 0.386 V (vs. SCE) pH 6.84.electrocatalysis | oxygen reduction | boron-doped diamond

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“…A classical intercalation model demands that the DNA helix must lengthen as base pairs are separated to accommodate a binding ligand, leading to an increase in DNA viscosity . In contrast, a partial and/or non ‐classical intercalation ligand could bend (or kink) the DNA helix, reducing its effective length and concomitantly reducing its viscosity, while ligands that bind exclusively in DNA grooves (e.g.…”

Section: Resultsmentioning

confidence: 99%

Water Soluble Nickel – metformin ternary complexes: Thermal, DNA binding and molecular docking studies

Rajeshwari

Vasantha

Kumar

et al. 2019

Applied Organom Chemis

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The Nickel (II) complexes [Ni(Cl)2(metf)(o‐phen)] (1), [Ni(Cl)2(metf)(opda)] (2), [Ni(Cl)2(metf)(en)](3), [Ni(Cl)2(metf)(2,2'‐bipy)](4), (metf = metformin, o‐phen = ortho‐phenanthroline, opda = ortho‐phenylenediamine, en = ethylenediamine, 2–2′ bipy = 2–2′ bipyridyl) were synthesized and characterized using LC–MS, elemental analysis, molar conductance measurements, TGA‐DTA, IR spectroscopy, magnetic moment measurements and electronic spectroscopy. The central Ni2+ was found to be in octahedral geometry. The DNA interaction of these complexes have been studied by UV–visible absorption studies, fluorescence emission technique and viscosity measurement. The complexes showed absorption hyperchromism in UV–visible spectra with calf thymus DNA. The binding constants from UV–visible absorption studies were 7.42 × 104, 0.74 × 104, 3.19 × 104, 5.9 × 104 M−1 for 1, 2, 3 and 4, respectively and Stern‐Volmer quenching constants from fluorescence studies were 0.16, 0.41, 0.23, 0.18, respectively. Viscosity measurements revealed that the binding of the complexes with DNA could be surface binding, mainly due to groove binding. The highest DNA cleavage activity of the complexes is recorded for complex 1. The complexes were docked in to B‐DNA sequence, 5′(D*AP*CP*CP*GP*AP*CP* GP*TP*CP*GP*GP*T)‐3′ retrieved from protein data bank (PDB ID: 423D), using Discovery Studio 2.1 software. C Docker Intectraction energy of 1, 2, 3 and 4 complexes is 32.027, 31.427, 35.393 and 30.521 respectively. The highest docking score is seen for complex 3.

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DNA-binding study of anthraquinone derivatives using Chemometrics methods

Cited by 58 publications

References 68 publications

Design and synthesis of novel hydroxyanthraquinone nitrogen mustard derivatives as potential anticancer agents via a bioisostere approach

Design and synthesis of novel hydroxyanthraquinone nitrogen mustard derivatives as potential anticancer agents via a bioisostere approach

The electrochemistry of quinizarin revealed through its mediated reduction of oxygen

Water Soluble Nickel – metformin ternary complexes: Thermal, DNA binding and molecular docking studies

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