A Cationic Zinc Porphyrin as a Chiroptical Probe for Z‐DNA

Baláž, Milan; Napoli, M.; Holmes, Andrea E.; Mammana, Angela; Nakanishi, Koji; Berova, Nina; Purrello, Roberto

doi:10.1002/anie.200501149

Cited by 120 publications

(81 citation statements)

References 37 publications

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“…One interesting consequence of the chiral structure of DNA is the induction of chiral effects, such as induced circular dichroism, in achiral molecules interacting with it, a property than can be profitably exploited for the study of small molecule-DNA interactions or to selectively probe DNA conformations, as in the case of the interaction of porphyrins, [21][22][23] acridine, 24 or cyanine dyes with dsDNA or its analogs. 25 The full description of these effects is beyond the scope of this review, which focuses on the chirality of the species interacting with DNA.…”

Section: Chirality and Handedness In The Structure Of Nucleic Acidsmentioning

confidence: 99%

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

et al. 2007

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The understanding of the interaction of chiral species with DNA or RNA is very important for the development of new tools in biology and of new drugs. Several cases in which chirality is a crucial point in determining the DNA binding mode are reviewed and discussed, with the aim of illustrating how chirality can be considered as a tool for improving the understanding of mechanisms and the effectiveness of nucleic acid recognition. The review is divided into two parts: the former describes examples of chiral species interacting with DNA: intercalators, metal complexes, and groove binders; the latter part is dedicated to chirality in DNA analogs, with discussion of phosphate stereochemistry and chirality of ribose substitutes, in particular of peptide nucleic acids (PNAs) for which a number of works have been published recently dealing with the effect of chirality in DNA recognition. The discussion is intended to show how enantiomeric recognition originates at the molecular level, by exploiting the enormous progresses recently achieved in the field of structural characterization of complexes formed by nucleic acid with their ligands by crystallographic and spectroscopic methods. Examples of application of the DNA binding molecules described and the role of chirality in DNA recognition relevant for biotechnology or medicinal chemistry are reported.

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Section: Chirality and Handedness In The Structure Of Nucleic Acidsmentioning

confidence: 99%

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

et al. 2007

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“…However, higher energy left-handed forms, the so-called Z conformations, can be accessed under certain conditions. 55 While the biological role of Z-DNA is still under scientific scrutiny, there is a need to identify it selectively. Methods for such identification include CD spectroscopy.…”

Section: Dnamentioning

confidence: 99%

“…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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“…Balaz et al reported in 2005 the recognition of Z DNA by the zinc(ii) complex of 5,10,15,20-tetrakis-(4-N-methylpyridinium)porphyrin. [21] The zinc porphyrin was added to a previously induced Z-DNA form of poly d(GC) and a CD signal in the visible range recorded. We reproduced these experiments with porphyrins that contained different metals in the centre.…”

Section: Ongoing Workmentioning

confidence: 99%

Interaction of Novel Metal Complexes with DNA: Synthetic and Structural Aspects

Spingler¹,

Pieve²,

Medina‐Molner³

et al. 2009

Chimia

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Metal ions bind to nucleic acids at various positions. This binding can be modulated by using metal complexes with appropriate ligands. Novel mono- and especially dinuclear metal complexes could be a powerful tool to detect rare, but still physiologically relevant, forms of DNA, e.g. the left-handed Z-DNA. In this review, our recent research activities in this area of bioinorganic chemistry are summarized. A special emphasis is laid on the synthetic challenges that arose upon the synthesis of the polyamine ligands. Further, some rather unusual approaches to elucidate the solution structure of copper bound to guanosine monophosphate with the help of pulsed EPR techniques like ENDOR and HYSCORE are described

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A Cationic Zinc Porphyrin as a Chiroptical Probe for Z‐DNA

Cited by 120 publications

References 37 publications

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

Porphyrins and Expanded Porphyrins as Receptors

Interaction of Novel Metal Complexes with DNA: Synthetic and Structural Aspects

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