Recognition of Single Stranded and Double Stranded DNA/RNA Sequences in Aqueous Medium by Small Bis-Aromatic Derivatives

Tumir, Lidija-Marija; Piantanida, Ivo

doi:10.2174/138955710791330990

Cited by 13 publications

(3 citation statements)

References 48 publications

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“…The binding of cationic porphyrin derivatives to nucleic acids has been the subject of extensive research and recently some bioactive moieties were introduced onto the periphery of cationic porphyrins in order to utilize the tetrapyrrole macrocycle as DNA targeting agent . Bis‐intercalating compounds show higher DNA binding affinities and slower dissociation rates than the corresponding monomers and a great number of dimeric forms of DNA intercalators has been developed as potential anticancer drugs . To achieve e selective recognition of DNA sequences, Byron and Voyer linked two cationic porphyrins on different positions of a α‐helical peptide (Table , entry 34), to orient properly two DNA intercalating moieties on this peptide framework.…”

Section: Biomarkers Detection and Emerging Therapiesmentioning

confidence: 99%

Porphyrin–peptide conjugates in biomedical applications

Biscaglia

Gobbo

2018

Peptide Science

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The conjugation of peptides to porphyrins and related tetrapyrrole based macrocycles have extended their applications in biological systems, where the photophysical properties of these molecules and their ability to coordinate metals can be exploited for detecting and opposing to the onset of important diseases. This review presents a survey of the published literature over last years on biomedical applications of these hybrid compounds, mostly in the field of photodynamic therapy (PDT), but also in sensing key metabolites and peculiar structures of biomolecules in living systems. Peptides based strategies to improve the efficacy of the photosensitizer (PS) in PDT will be discussed, as well as solutions to overcome some limitations recently emerged in the use of peptides as delivery vehicles. An overview on possible application of porphyrin–peptide conjugates in detection of biomarkers of physiological and pathological states will be also presented.

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Section: Biomarkers Detection and Emerging Therapiesmentioning

confidence: 99%

Porphyrin–peptide conjugates in biomedical applications

Biscaglia

Gobbo

2018

Peptide Science

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“…Nevertheless, the dynamic nature of nucleic acids, combined with structural differences between various DNA/RNA sequences, offer numerous highly interesting targets. Within the last two decades, the design of small binding molecules has mostly relied on the three-dimensional recognition of various targeted DNA/RNA sites [2–3], frequently relying upon new knowledge gained from supramolecular chemistry [4]. …”

Section: Introductionmentioning

confidence: 99%

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

Stojković

Škugor

Dudek

et al. 2014

Beilstein J. Org. Chem.

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SummaryAn investigation of the interactions of two novel and several known DBTAA–adenine conjugates with double-stranded DNA and RNA has revealed the DNA/RNA groove as the dominant binding site, which is in contrast to the majority of previously studied DBTAA analogues (DNA/RNA intercalators). Only DBTAA–propyladenine conjugates revealed the molecular recognition of AT-DNA by an ICD band pattern > 300 nm, whereas significant ICD bands did not appear for other ds-DNA/RNA. A structure–activity relation for the studied series of compounds showed that the essential structural features for the ICD recognition are a) the presence of DNA-binding appendages (adenine side chain and positively charged side chain) on both DBTAA side chains, and b) the presence of a short propyl linker, which does not support intramolecular aromatic stacking between DBTAA and adenine. The observed AT-DNA-ICD pattern differs from previously reported ss-DNA (poly dT) ICD recognition by a strong negative ICD band at 350 nm, which allows for the dynamic differentiation between ss-DNA (poly dT) and coupled ds-AT-DNA.

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“…Naphtalene diimide (NDI) scaffold is present in a wide number of potential anticancer agents which interact with DNA preferentially as intercalators [1][2][3][4][5] . Additionally, some derivatives characterized by this core have been optimized to exhibit bis-threading intercalating ability 6 , to enhance the stabilization of DNA triplexes 7 , to stabilize 8 or alkylate 9,10 G-quadruplex DNA structure.…”

Section: Introductionmentioning

confidence: 99%

Structure–activity relationships of novel substituted naphthalene diimides as anticancer agents

Milelli

Tumiatti

Micco

et al. 2012

European Journal of Medicinal Chemistry

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Novel 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity on a wide number of different tumor cell lines. The prototypes of the present series were derivatives 1 and 2 characterized by interesting biological profiles as anticancer agents. The present investigation expands on the study of structure-activity relationships of prototypes 1 and 2, namely, the influence of the different substituents of the phenyl rings on the biological activity. Derivatives 3-22, characterized by a different substituent on the aromatic rings and/or a different chain length varying from two to three carbon units, were synthesized and evaluated for their cytostatic and cytotoxic activities. The most interesting compound was 20, characterized by a linker of three methylene units and a 2,3,4-trimethoxy substituent on the two aromatic rings. It displayed antiproliferative activity in the submicromolar range, especially against some different cell lines, the ability to inhibit Taq polymerase and telomerase, to trigger caspase activation by a possible oxidative mechanism, to downregulate ERK 2 protein and to inhibit ERKs phosphorylation, without acting directly on microtubules and tubuline. Its theoretical recognition against duplex and quadruplex DNA structures have been compared to experimental thermodynamic measurements and by molecular modeling investigation leading to putative binding modes. Taken together these findings contribute to define this compound as potential Multitarget-Directed Ligands interacting simultaneously with different biological targets.

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Recognition of Single Stranded and Double Stranded DNA/RNA Sequences in Aqueous Medium by Small Bis-Aromatic Derivatives

Cited by 13 publications

References 48 publications

Porphyrin–peptide conjugates in biomedical applications

Porphyrin–peptide conjugates in biomedical applications

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

Structure–activity relationships of novel substituted naphthalene diimides as anticancer agents

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