Binding of inert metal complexes to deoxyribonucleic acid detected by linear dichroism

Nordén, Bengt; Tjerneld, Folke

doi:10.1016/0014-5793(76)80566-2

Cited by 101 publications

(52 citation statements)

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“…54 Nordé n and Tjerneld first reported the preference of the D-enantiomer of [Fe(bipy) 3 ] 2þ for the right-handed B-form DNA. 55 The two enantiomers of [Ru(phen) 3 ] 2þ , 56 as well as analogous complexes of rhodium and cobalt, 57 bind to DNA and whether they interact in one of the grooves or are intercalated between the DNA base pairs has been the matter of intense discussion for many years; however, most data are consistent with a model where the complexes bind by semi-intercalating one of the phenanthroline moieties between the base pairs of DNA. 58 As early as 1984, the enantioselectivity in the DNA binding of metal complexes, such as tris(2,7-diphenilphenantroline)ruthenium (II), in which the aromatic moieties of phenantroline was further extended, was clearly established by Barton selectively interacted with the left-handed Z-DNA, 59 suggesting a correlation between the handedness of the propeller-like complex and that of the host DNA.…”

Section: Intercalatorsmentioning

confidence: 95%

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: Intercalatorsmentioning

confidence: 95%

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

et al. 2007

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“…[9,10] Recently, it has been reported that the enantiomeric pairs of daunorubicin or helicene display structural selectivity in binding to B-or Z-DNA. [11] However, none of these systems can be used as chiroptical probes because recognition of the Z or B forms is not reflected in unique spectroscopic features, such as new CD bands, which unequivocally show the detection event.…”

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

et al. 2005

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“…Norden and Tjerneld (11) first reported the preference of the ⌬ enantiomer of Tris(dipyridyl)Fe(II) for right-handed B-form DNA. The Barton laboratory subsequently developed an elaborate series of chiral metal complexes, some of which were reported to recognize specific DNA conformational features (for reviews, see refs.…”

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Allosteric, chiral-selective drug binding to DNA

Trent

Fokt

et al. 2000

Proc. Natl. Acad. Sci. U.S.A.

155

150

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DNA is polymorphic and exists in a variety of distinct conformations (1, 2). Duplex DNA can adopt a variety of sequence-dependent secondary structures that range from the canonical right-handed B form through the left-handed Z conformation. Multistranded triplex and tetraplex structures are now known to exist. All of these unique conformations may play important functional roles in gene expression. Consequently, there is intense current interest in the design and synthesis of small molecules that selectively target specific DNA structures, to inhibit the biological function in which these particular structures participate (3-10).Enantiomers of chiral metal complexes have attracted considerable attention as potential structural probes of DNA conformation. Norden and Tjerneld (11) first reported the preference of the ⌬ enantiomer of Tris(dipyridyl)Fe(II) for right-handed B-form DNA. The Barton laboratory subsequently developed an elaborate series of chiral metal complexes, some of which were reported to recognize specific DNA conformational features (for reviews, see refs. 12-14). A comprehensive review of the interaction of chiral metal complexes with DNA (15) indicated, however, that the structural selectivity of these agents is ambiguous in many cases.We report here a dramatic and unambiguous example of structural selectivity in DNA binding for the naturally occurring anticancer agent (ϩ)-daunorubicin and its novel (Ϫ)-enantiomer, WP900 (Fig. 1). The synthesis of WP900 proved to be demanding and required some 37 steps. We find that the daunorubicin͞WP900 enantiomeric pair can discriminate between right-and left-handed DNA, and that each compound can act as an allosteric effector to convert DNA to a conformation that binds each ligand with higher affinity. The structural selectivities of daunorubicin and WP900 appear to be far greater than those reported to date for any chiral metal compound. To the best of our knowledge, there have been no other reports of a detailed investigation of DNA binding for an enantiomeric pair that does not involve a chiral metal complex. Materials and MethodsMaterials. Daunorubicin was obtained from Sigma and was used without further purification. The concentrations of daunorubicin solutions were determined by optical absorption at 480 nm by using 480 ϭ 11,500 M Ϫ1 ⅐cm Ϫ1

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Binding of inert metal complexes to deoxyribonucleic acid detected by linear dichroism

Cited by 101 publications

References 5 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

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

Allosteric, chiral-selective drug binding to DNA

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