Circular dichroism and the interactions of water soluble porphyrins with DNA—A minireview

Pasternack, Robert F.

doi:10.1002/chir.10206

Cited by 180 publications

(133 citation statements)

References 21 publications

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“…However, the phosphate residues of DNA/RNA produce negative charges that require cationic porphyrins as suitable counterparts for the effective self-assembly process. In general, there are three major binding modes for the porphyrin-DNA/RNA complexes: intercalation between the base pairs, binding to the major or minor grooves and outside stacking, depending upon the porphyrin and polynucleotide structures and media [98][99][100][101]. The chiroptical responses from these types of supramolecular complexation were also well established, reflecting the orientation of porphyrin electronic transitions in relation to the chirally arranged bases of DNA/RNA and interporphyrin coupling within the porphyrin aggregates stacked in a chiral fashion along the double helix.…”

Section: Achiral Porphyrinoidsmentioning

confidence: 99%

Supramolecular Chirality in Porphyrin Chemistry

Borovkov

2014

Symmetry

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Supramolecular chirality, being an intelligent combination of supramolecular chemistry and chiral science, plays a decisive role in the functioning of various natural assemblies and has attracted much attention from the scientific community, due to different applications in modern technologies, medicine, pharmacology, catalysis and biomimetic research. Porphyrin molecules are of particular interest to study this phenomenon owing to their unique spectral, physico-chemical and synthetic properties. This review highlights the most important types of chiral porphyrin structures by using the best-suited representative examples, which are frequently used in the area of supramolecular chirality.

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Section: Achiral Porphyrinoidsmentioning

confidence: 99%

Supramolecular Chirality in Porphyrin Chemistry

Borovkov

2014

Symmetry

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“…be anticipated [47]. It is generally accepted that a single negative band indicative for the intercalation [48,49], and a positive band belongs to externally bound porphyrin at DNA grooves [37].…”

Section: Accepted M Manuscriptmentioning

confidence: 99%

Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates

Mező

Herényi

Habdas

et al. 2011

Biophysical Chemistry

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT AbstractRecently cationic porphyrin-peptide conjugates were synthesized to enhance the cellular uptake of porphyrins or deliver the peptide moiety to the close vicinity of nucleic acids. DNA binding of such compounds was not systematically studied yet.We synthesized two new porphyrin-tetrapeptide conjugates which can be considered as a typical monomer unit corresponding to the branches of porphyrin-polymeric branched chain polypeptide conjugates. Tetra-peptides were linked to the tri-cationic meso-tri A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT Graphical AbstractResearch Highlights We synthesized two new porphyrin-tetrapeptide conjugates. DNA binding of porphyrin conjugates was studied with spectroscopic methods. Peptide conjugates of cationic porphyrins bind to DNA by two distinct binding modes. Binding modes can be identified as intercalation and external binding.

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“…This suggests that MAA and Cd-MAA can unwind the DNA helix and lead to the loss of helicity. 30,31 The larger decrease in the CD band intensity, caused by Cd-MAA compared to MAA at the same concentration, implies that Cd-MAA is more effective than MAA in perturbing the secondary structure of DNA.…”

Section: Genotoxicities Of Different Nanoparticles Residual Transformmentioning

confidence: 99%

The cadmium–mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots

Tang¹,

Fan²,

He³

et al. 2012

IJN

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Quantum dots (QDs) have many potential clinical and biological applications because of their advantages over traditional fluorescent dyes. However, the genotoxicity potential of QDs still remains unclear. In this paper, a plasmid-based system was designed to explore the genotoxic mechanism of QDs by detecting changes in DNA configuration and biological activities. The direct chemicobiological interactions between DNA and mercaptoacetic acid-coated CdSecore QDs (MAA-QDs) were investigated. After incubation with different concentrations of MAA-QDs (0.043, 0.13, 0.4, 1.2, and 3.6 µmol/L) in the dark, the DNA conversion of the covalently closed circular (CCC) DNA to the open circular (OC) DNA was significantly enhanced (from 13.9% ± 2.2% to 59.9% ± 12.8%) while the residual transformation activity of plasmid DNA was greatly decreased (from 80.7% ± 12.8% to 13.6% ± 0.8%), which indicated that the damages to the DNA structure and biological activities induced by MAA-QDs were concentration-dependent. The electrospray ionization mass spectrometry data suggested that the observed genotoxicity might be correlated with the cadmium-mercaptoacetic acid complex (Cd-MAA) that is formed in the solution of MAA-QDs. Circular dichroism spectroscopy and transformation assay results indicated that the Cd-MAA complex might interact with DNA through the groove-binding mode and prefer binding to DNA fragments with high adenine and thymine content. Furthermore, the plasmid transformation assay could be used as an effective method to evaluate the genotoxicities of nanoparticles.

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Circular dichroism and the interactions of water soluble porphyrins with DNA—A minireview

Cited by 180 publications

References 21 publications

Supramolecular Chirality in Porphyrin Chemistry

Supramolecular Chirality in Porphyrin Chemistry

Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates

The cadmium–mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots

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Circular dichroism and the interactions of water soluble porphyrins with DNA—A minireview

Cited by 180 publications

References 21 publications

Supramolecular Chirality in Porphyrin Chemistry

Supramolecular Chirality in Porphyrin Chemistry

Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates

The cadmium&ndash;mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots

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The cadmium–mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots