Interactions of a Tetraanionic Porphyrin with DNA: from a Z-DNA Sensor to a Versatile Supramolecular Device

D’Urso, Alessandro; Mammana, Angela; Baláž, Milan; Holmes, Andrea E.; Berova, Nina; Lauceri, Rosaria; Purrello, Roberto

doi:10.1021/ja808099u

Cited by 120 publications

(72 citation statements)

References 23 publications

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“…It was shown that out of water-soluble tetra-cationic 5,10,15‚20-tetra(N-methylpyridinium-4-yl)porphyrin (TMPyP) naturally drawn to the DNA polyanion, tri-or dicationic derivatives also bind to DNA by intercalation or by external binding (Pasternack et al 1983;Shui et al 2000;Zupan et al 2004;D'Urso et al 2009;Gong et al 2012;Accetta et al 2015).…”

Section: Introductionmentioning

confidence: 99%

Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

et al. 2017

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Recently we have characterized the DNA and nucleoprotein (NP) binding of bis(4-Nmethylpyridyl)-15,20-di(4-carboxyphenyl)porphyrin (BMPCP) and meso-tri(4-Nmethylpyridyl)-mono(4-carboxyphenyl)porphyrin (TMPCP) and their tetra-peptide conjugates (BMPCP-4P 2 and TMPCP-4P, respectively). In this work we investigated the interaction of TMPCP conjugated to the tetra-peptide branches of branched chain polymeric polypeptide with poly-L-lysine backbone (AK) with DNA or NP using spectroscopic methods.Analysis of absorption spectra revealed the external binding, but no intercalation of TMPCP-AK to DNA. There was no evidence for the interaction between TMPCP-AK and encapsidated DNA. Furthermore, we examined the cellular uptake of BMPCP and TMPCP and their tetra-or polypeptide conjugates by flow cytometry and analyzed how charge, size and structure of the compounds affect their incorporation. In comparison, liposomal association constants of these derivatives were determined. BMPCP-4P 2 accumulated the most, and porphyrins with two positive charges (BMPCP and BMPCP-4P 2 ) showed better accumulation than the tri-cationic TMPCP or TMPCP-4P.Cellular uptake of polycationic TMPCP-AK was significantly lower than that of the free or tetra-peptide conjugated derivatives. The sub-cellular localization of all the five compounds was investigated in co-localization studies by confocal microscopy with special attention to their nuclear localization. Neither free nor conjugated BMPCP or TMPCP were co-localized with nuclear marker. Instead, these derivatives showed co-localization with lysosomal and mitochondrial fluorescent probes. TMPCP-AK conjugate had different localization pattern appearing mainly in mitochondria and cytoplasmic vesicles.Our results may contribute to the further design of DNA targeting porphyrin based constructs.

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Section: Introductionmentioning

confidence: 99%

Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

et al. 2017

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“…Porphyrins are also one of the most studied DNA binding agents [6,7]. The binding of cationic porphyrin derivatives to nucleic acids has been the subject of extensive research since Fiel and colleagues discovered that these compounds can form various complexes with DNA [8].…”

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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“…There are two recent reports wherein porphyrins are used to distinguish between these two types of DNA. 55,56 In 2005, Purrello and coworkers reported the pentacoordinated cationic zinc-porphyrin-based chiroptical probe, 23·H 2 O, and demonstrated its ability to discriminate between B and Z structures. A desirable chiroptical probe is one that absorbs above 300 nm-an area free from interference of most biological species.…”

Section: Dnamentioning

confidence: 99%

Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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This chapter summarizes recent efforts to use porphyrins and expanded porphyrins as receptors. These unique macrocycles bear resemblance to naturally occurring tetrapyrrolic pigments and have been studied extensively as building blocks for a variety of functional molecular receptors. The introduction discusses the inherent characteristics of porphyrins and their analogs from the perspective of receptor design and is designed to highlight key features. These features include ease of synthesis and functionalization, the hydrogen‐bonding ability of the constituent pyrrolic NH protons, and the fact that the systems in question are often highly colored. This latter feature has afforded an extremely useful means of analyzing host–guest interactions. Because of space limitations, not all of the literature on this topic could be covered in a comprehensive manner. The definition of “receptor” is also limited to species that are thought to be operated via strictly noncovalent‐ or supramolecular‐type interactions. However, this definition is expanded in a few special cases. The goal of this article is not to cite every published article on this topic, but to highlight interesting examples of porphyrin and expanded porphyrins and their utility as receptors. An effort has also been made to describe the analytical techniques used to characterize the resulting host–guest ensembles. This chapter is organized according to the type of guest. One section covers the relatively new area of supramolecular π–π interactions involving porphyrins and nanomaterials, such as fullerenes and nanotubes. Another section discusses porphyrins as receptors for biological entities, including saccharides, peptides, and proteins, as well as DNA. The next section covers porphyrins and expanded porphyrins as anion receptors. This latter treatment includes a discussion of supramolecular electron‐transfer dyads. The use of porphyrins in sensing applications is also presented in summary form. Finally, a perspective on this rapidly growing field of supramolecular chemistry is included in the final remarks. It is hoped that the combination of cited references and listed further readings will allow the interested reader to learn more about this fast‐evolving and fascinating topic.

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Interactions of a Tetraanionic Porphyrin with DNA: from a Z-DNA Sensor to a Versatile Supramolecular Device

Cited by 120 publications

References 23 publications

Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates

Porphyrins and Expanded Porphyrins as Receptors

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