Changes in Superhelical Density of Closed Circular Deoxyribonucleic Acid by Intercalation of Anti-R-Plasmid Drugs and Primaquine

Allison, Richard G.; Hahn, Fred E.

doi:10.1128/aac.11.2.251

Cited by 24 publications

(8 citation statements)

References 34 publications

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“…Acridine Orange has been investigated as a photodynamic therapy drug , Methylene Blue has been investigated as a sentinel lymph node marker , Neutral Red is a widely applied probe for assessment of the health status of marine organisms , and Toluidine Blue is applied as a diagnostic aid for the detection of oral cancer . Given such applications, it might be assumed that these dyes lack hazard, yet each of these compounds – as is the case with many other cationic colorants – has been shown by use of the Ames test, or one of its derivatives, to be a bacterial mutagen , and in addition to bind to dsDNA in solution . How should these apparent contradictions be understood?…”

Section: Case Example 1 – Predicting Dye Accumulation In Nucleic Acidmentioning

confidence: 99%

Where do dyes go inside living cells? Predicting uptake, intracellular localisation, and accumulation using QSAR models

Horobin

2014

Coloration Technology

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Uptake of dyes into living cells and organisms is of concern to several diverse groups of people. These include those not wishing dyes to enter cells (e.g. manufacturers and users of textile dyes, or laboratory workers using dyes as analytical reagents) and those requiring dye entry (e.g. biologists imaging cell contents, or clinicians using photoactive dyes as antitumour drugs). This diversity results in the need to consider an extremely wide range of dyes -and indeed of cells and organisms. An overview of methods for predicting uptake and intracellular localisation is provided, followed by a more detailed account of the concepts and procedures involved in decision-rule quantitative structure-activity relationship (QSAR) models. Some of these models permit the prediction of which dyes are likely to enter cells, and which dyes will be excluded. Other models predict where internalised dyes will localise within the live cells. Use of QSAR models to understand intracellular accumulation, redistribution, loss from the cell, and metabolic modification of dyes is also considered. In particular, the relationship of such predictions to toxicity is discussed. An extended case example is provided, describing the modelling of dye binding to nucleic acids in single-cell systems. A further case example then illustrates dye localisation in multicellular organisms. Finally, conclusions, critiques, and probable future directions concerning the QSAR modelling approach to dye uptake and localisation are given. A summary of key QSAR decision rules in the form of decision logic tabulations is provided.

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Section: Case Example 1 – Predicting Dye Accumulation In Nucleic Acidmentioning

confidence: 99%

Where do dyes go inside living cells? Predicting uptake, intracellular localisation, and accumulation using QSAR models

Horobin

2014

Coloration Technology

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“…Primaquine may not be the anti-malarial drug with the best therapeutic profiles [121,234], and several aspects of its biological action are yet to be discovered. However, primaquine is still the only transmission-blocking anti-malarial clinically useful and it goes on being used as the platform for developing novel anti-malarials with improved efficacy and reduced toxicity [21].…”

Section: Final Remarksmentioning

confidence: 99%

Primaquine revisited six decades after its discovery

Vale¹,

Moreira²,

Gomes³

2009

European Journal of Medicinal Chemistry

321

308

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“…5 Quinine (QN) belongs to a group of intercalative substances, such as ethidium bromide, quinacrine, and chloroquine, which change the superhelical density of DNA in vitro. 6 The quinoline ring of QN satisfies the criteria for this behavior, 7 although a second binding site exists, which is thought to be an electrostatic interaction between the tertiary amino group of quinuclidine and a groove of the DNA helix. 8 In this work, various stationary phases (SPs) were prepared and tested for pDNA topoisomer selectivity.…”

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confidence: 99%

Molecular Recognition Principles and Stationary-Phase Characteristics of Topoisomer-Selective Chemoaffinity Materials for Chromatographic Separation of Circular Plasmid DNA Topoisomers

2011

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We recently discovered the molecular recognition capability of a quinine carbamate ligand attached to silica as a powerful chemoaffinity material for the chromatographic separation of circular plasmid topoisomers of different linking numbers. In this paper we develop structure-selectivity relationship studies to figure out the essential structural features for topoisomer recognition. By varying different moieties of the original cinchonan-derived selector, it was shown that intercalation by the quinoline moiety of the ligand as assumed initially as the working hypothesis is not an essential feature for topoisomer recognition during chromatography. We found that the key elements for topoisomer selectivity are the presence of a rigid weak anion-exchange site and a H-donor site separated from each other in a defined distance by a 4-atom spacer. Additionally, incorporation of the weak anion-exchange site into a cyclic ring structure provides greater rigidity of the ligand molecule and turned out to be advantageous, if not mandatory, for (close to) baseline separation.

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Changes in Superhelical Density of Closed Circular Deoxyribonucleic Acid by Intercalation of Anti-R-Plasmid Drugs and Primaquine

Cited by 24 publications

References 34 publications

Where do dyes go inside living cells? Predicting uptake, intracellular localisation, and accumulation using QSAR models

Where do dyes go inside living cells? Predicting uptake, intracellular localisation, and accumulation using QSAR models

Primaquine revisited six decades after its discovery

Molecular Recognition Principles and Stationary-Phase Characteristics of Topoisomer-Selective Chemoaffinity Materials for Chromatographic Separation of Circular Plasmid DNA Topoisomers

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