Fluorescent Analogues of FRH Peptide: Cu(II) Binding and Interactions with ds-DNA/RNA

Košćak, Marta; Krošl, Ivona; Žinić, Mladen; Piantanida, Ivo

doi:10.3390/chemosensors10010034

Cited by 5 publications

(2 citation statements)

References 46 publications

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“…The same group also developed a series of modified peptides with incorporated aminonaphthalimide as a fluorophore [26]. Furthermore, the binding of a series of fluorophore-modified oligopeptides to polynucleotides has been investigated [27][28][29], where the binding units were phenantridines [27], pyrenes [28], naphthalenedimide [30], guanidinocarbonylpyrroles [27] or coumarins [31].…”

Section: Introductionmentioning

confidence: 99%

Dipeptides Containing Pyrene and Modified Photochemically Reactive Tyrosine: Noncovalent and Covalent Binding to Polynucleotides

Sviben,

Glavaš,

Erben

et al. 2023

Molecules

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Dipeptides 1 and 2 were synthesized from unnatural amino acids containing pyrene as a fluorescent label and polynucleotide binding unit, and modified tyrosine as a photochemically reactive unit. Photophysical properties of the peptides were investigated by steady-state and time-resolved fluorescence. Both peptides are fluorescent (Φf = 0.3–0.4) and do not show a tendency to form pyrene excimers in the concentration range < 10−5 M, which is important for their application in the fluorescent labeling of polynucleotides. Furthermore, both peptides are photochemically reactive and undergo deamination delivering quinone methides (QMs) (ΦR = 0.01–0.02), as indicated from the preparative photomethanolysis study of the corresponding N-Boc protected derivatives 7 and 8. Both peptides form stable complexes with polynucleotides (log Ka > 6) by noncovalent interactions and similar affinities, binding to minor grooves, preferably to the AT reach regions. Peptide 2 with a longer spacer between the fluorophore and the photo-activable unit undergoes a more efficient deamination reaction, based on the comparison with the N-Boc protected derivatives. Upon light excitation of the complex 2·oligoAT10, the photo-generation of QM initiates the alkylation, which results in the fluorescent labeling of the oligonucleotide. This study demonstrated, as a proof of principle, that small molecules can combine dual forms of fluorescent labeling of polynucleotides, whereby initial addition of the dye rapidly forms a reversible high-affinity noncovalent complex with ds-DNA/RNA, which can be, upon irradiation by light, converted to the irreversible (covalent) form. Such a dual labeling ability of a dye could have many applications in biomedicinal sciences.

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Section: Introductionmentioning

confidence: 99%

Dipeptides Containing Pyrene and Modified Photochemically Reactive Tyrosine: Noncovalent and Covalent Binding to Polynucleotides

Sviben,

Glavaš,

Erben

et al. 2023

Molecules

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“…Electronic absorption data a , absorption maxima, and fluorescence data of benzothiazoles 1-9. Sodium cacodylate buffer, I = 0.05 mol dm −3 , pH = 7.0; b in fluorescence titrations λ max was 320 nm; c Absolute fluorescence quantum yield was determined by integrating sphere SC-30, Edinburgh Inst., for argon-purged solutions; QY ± 0.5 • C [47]…”

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confidence: 99%

Recognition of ATT Triplex and DNA:RNA Hybrid Structures by Benzothiazole Ligands

et al. 2022

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Interactions of an array of nucleic acid structures with a small series of benzothiazole ligands (bis-benzothiazolyl-pyridines—group 1, 2-thienyl/2-benzothienyl-substituted 6-(2-imidazolinyl)benzothiazoles—group 2, and three 2-aryl/heteroaryl-substituted 6-(2-imidazolinyl)benzothiazoles—group 3) were screened by competition dialysis. Due to the involvement of DNA:RNA hybrids and triplex helices in many essential functions in cells, this study’s main aim is to detect benzothiazole-based moieties with selective binding or spectroscopic response to these nucleic structures compared to regular (non-hybrid) DNA and RNA duplexes and single-stranded forms. Complexes of nucleic acids and benzothiazoles, selected by this method, were characterized by UV/Vis, fluorescence and circular dichroism (CD) spectroscopy, isothermal titration calorimetry, and molecular modeling. Two compounds (1 and 6) from groups 1 and 2 demonstrated the highest affinities against 13 nucleic acid structures, while another compound (5) from group 2, despite lower affinities, yielded higher selectivity among studied compounds. Compound 1 significantly inhibited RNase H. Compound 6 could differentiate between B- (binding of 6 dimers inside minor groove) and A-type (intercalation) helices by an induced CD signal, while both 5 and 6 selectively stabilized ATT triplex in regard to AT duplex. Compound 3 induced strong condensation-like changes in CD spectra of AT-rich DNA sequences.

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Copper coordination-driven self-assembly and encapsulation of PCR reagents

Zheng

Liu

2024

Chinese Chemical Letters

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Fluorescent Analogues of FRH Peptide: Cu(II) Binding and Interactions with ds-DNA/RNA

Cited by 5 publications

References 46 publications

Dipeptides Containing Pyrene and Modified Photochemically Reactive Tyrosine: Noncovalent and Covalent Binding to Polynucleotides

Dipeptides Containing Pyrene and Modified Photochemically Reactive Tyrosine: Noncovalent and Covalent Binding to Polynucleotides

Recognition of ATT Triplex and DNA:RNA Hybrid Structures by Benzothiazole Ligands

Copper coordination-driven self-assembly and encapsulation of PCR reagents

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