DNA Interaction and Photocleavage Properties of Porphyrins Containing Cationic Substituents at the Peripheral Position

Mettath, Sashikumar; Munson, Benjamin R.; Pandey, Ravindra K.

doi:10.1021/bc9800872

Cited by 100 publications

(56 citation statements)

References 39 publications

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“…At physiological conditions, non-enveloped viruses have negatively charged capsids and enveloped viruses harbour negatively charged glycoproteins on their surface, and are thus likely directly targeted by cationic porphyrins via electrostatic interactions, like previously described for Gram(−) bacteria (Karlin and Brendel 1988;Michen and Graule 2010;Liu et al 2015). Nucleic acids can also be directly targeted by both cationic porphyrins and phthalocyanines, and PDT can induce photocleavage of both RNA and DNA viruses (Abe and Wagner 1995;Moor et al 1997;Mettath et al 1999;Zupan et al 2005;Lopez Zeballos et al 2014). Nonetheless, to what extent such intercalation and cleavage contributes to virus inhibition in comparison to other possible mechanisms is not clear (Zupan et al 2005).…”

Section: Molecular Targets Of Antiviral Pactmentioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

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Photodynamic therapy (PDT) combines a photosensitiser, light and molecular oxygen to induce oxidative stress that can be used to kill pathogens, cancer cells and other highly proliferative cells. There is a growing number of clinically approved photosensitisers and applications of PDT, whose main advantages include the possibility of selective targeting, localised action and stimulation of the immune responses. Further improvements and broader use of PDT could be accomplished by designing new photosensitisers with increased selectivity and bioavailability. Porphyrin-based photosensitisers with amphiphilic properties, bearing one or more positive charges, are an effective tool in PDT against cancers, microbial infections and, most recently, autoimmune skin disorders. The aim of the review is to present some of the recent examples of the applications and research that employ this specific group of photosensitisers. Furthermore, we will highlight the link between their structural characteristics and PDT efficiency, which will be helpful as guidelines for rational design and evaluation of new PSs.

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Section: Molecular Targets Of Antiviral Pactmentioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

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“…They have been used in light-activated cancer treatment (photodynamic therapy) [1], in sensor design due to their fluorescent and electrochemical properties [2] and in gene therapy [3], they are the functional elements of light harvesting systems [4] and they could be used as artificial endonucleases [5].…”

Section: Introductionmentioning

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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“…Cationic porphyrins are known not only to bind and cleave DNA, but to be used for the cancer treatment. 4 Cationic porphyrins, especially meso-tetrakis (N-methylpyridinium-4-yl) porphyrin (H 2 TMPyP) and its metal complexes, possess significant and wide research value for the reason that they possess good water solubility, which makes DNA-binding possible under physiological conditions and interact with DNA strongly. 5,6 Meanwhile, tris-, tetra-and multiple charge cationic porphyrins are also known as good photosensitizers for DNA photocleavage.…”

Section: 3mentioning

confidence: 99%

Synthesis, DNA Photocleavage and Singlet Oxygen Measurement of Cationic Bisporphyrins

Wang¹,

Jin²,

Zhang³

et al. 2013

Journal of the Korean Chemical Society

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ABSTRACT. With −OCH2CO− as a linker, a non β-substituted cationic bisporphyrin (4a) and a β-substituted cationic bisporphyrin (4b) were prepared through methylation of the intermediate which was obtained from β-amino-5,10,15,20-tetra (4-cyanophenyl) porphyrin or 5-hydroxylphenyl-10,15,20-tris(4-cyanophenyl) reacting with 5-hydroxy-10,15,20-trispyridinylporphyrin. Their structures were confirmed by 1 H NMR, IR, UV-vis, MS and elemental analysis. DNA photocleavage ability and the singlet oxygen ability of those cationic bisporphyrins were investigated. DNA photocleavage activity of β-substituted cationic bisporphyrin was significantly weaker than that of H2TMPyP, but similar to that of non β-substituted cationic bisporphyrin. While 4a and 4b showed substantial photocleavage activities toward DNA, with 68% and 66% observed at 10 µM. The assessment of indirectly measured 1 O2 production rates against H2TMPyP were described and the relative singlet oxygen production yields were: free cationic bisporphyrins > H2TMPyP. The results showed the cationic bisporphyrins with β-substitution and non β-substitution could be developed as potential photodynamic agents.

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DNA Interaction and Photocleavage Properties of Porphyrins Containing Cationic Substituents at the Peripheral Position

Cited by 100 publications

References 39 publications

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates

Synthesis, DNA Photocleavage and Singlet Oxygen Measurement of Cationic Bisporphyrins

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