scholarly journals Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

2021 ◽  
Vol 17 ◽  
pp. 991-1000
Author(s):  
Peter Jonas Wickhorst ◽  
Mathilda Blachnik ◽  
Denisa Lagumdzija ◽  
Heiko Ihmels
Keyword(s):  
Dna Binding ◽  
Coupling Reaction ◽  
Spectroscopic Studies ◽  
Binding Properties ◽  
Quadruplex Dna ◽  
G4 Dna ◽  
Fluorescence Light ◽  
Berberine Derivatives ◽  
Ct Dna ◽  
Dna Binding Properties

Eleven novel 10-O-aryl-substituted berberrubine and berberine derivatives were synthesized by the Cu2+-catalyzed Chan–Evans–Lam coupling of berberrubine with arylboronic acids and subsequent 9-O-methylation. The reaction is likely introduced by the Cu2+-induced demethylation of berberrubine and subsequent arylation of the resulting 10-oxyanion functionality. Thus, this synthetic route represents the first successful Cu-mediated coupling reaction of berberine substrates. The DNA-binding properties of the 10-O-arylberberine derivatives with duplex and quadruplex DNA were studied by thermal DNA denaturation experiments, spectrometric titrations as well as CD and LD spectroscopy. Fluorimetric DNA melting analysis with different types of quadruplex DNA revealed a moderate stabilization of the telomeric quadruplex-forming oligonucleotide sequence G3(TTAG3)3. The derivatives showed a moderate affinity towards quadruplex DNA (K b = 5–9 × 105 M−1) and ct DNA (K b = 3–5 × 104 M−1) and exhibited a fluorescence light-up effect upon complexation to both DNA forms, with slightly higher intensity in the presence of the quadruplex DNA. Furthermore, the CD- and LD-spectroscopic studies revealed that the title compounds intercalate into ct DNA and bind to G4-DNA by terminal stacking.

scholarly journals Berberrubine Phosphate: A Selective Fluorescent Probe for Quadruplex DNA

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2566
Author(s):  
Peter Jonas Wickhorst ◽  
Heiko Ihmels
Keyword(s):  
Duplex Dna ◽  
Binding Modes ◽  
Strong Fluorescence ◽  
Binding Properties ◽  
Thermally Induced ◽  
Quadruplex Dna ◽  
G4 Dna ◽  
Fluorescence Light ◽  
Dna Binders ◽  
Ct Dna

A phosphate-substituted, zwitterionic berberine derivative was synthesized and its binding properties with duplex DNA and G4-DNA were studied using photometric, fluorimetric and polarimetric titrations and thermal DNA denaturation experiments. The ligand binds with high affinity toward both DNA forms (Kb = 2–7 × 105 M−1) and induces a slight stabilization of G4-DNA toward thermally induced unfolding, mostly pronounced for the telomeric quadruplex 22AG. The ligand likely binds by aggregation and intercalation with ct DNA and by terminal stacking with G4-DNA. Thus, this compound represents one of the rare examples of phosphate-substituted DNA binders. In an aqueous solution, the title compound has a very weak fluorescence intensity (Φfl < 0.01) that increases significantly upon binding to G4-DNA (Φfl = 0.01). In contrast, the association with duplex DNA was not accompanied by such a strong fluorescence light-up effect (Φfl < 0.01). These different fluorimetric responses upon binding to particular DNA forms are proposed to be caused by the different binding modes and may be used for the selective fluorimetric detection of G4-DNA.

Spectroscopic Studies on the Binding Properties of Ofloxacin and Human Telomeric G-Quadruplex DNA

2013 ◽  
Vol 634-638 ◽  
pp. 1062-1065 ◽  
Author(s):  
Xu Jian Luo ◽  
Qi Pin Qin ◽  
Yu Lan Li ◽  
Yan Yang
Keyword(s):  
Spectral Analysis ◽  
Fluorescence Emission ◽  
Spectroscopic Studies ◽  
Binding Properties ◽  
Quadruplex Dna ◽  
G4 Dna ◽  
G Quadruplex ◽  
Shoulder Peak ◽  
Binding Intensity ◽  
Dna Complex

The binding of ofloxacin with human telomeric G-quadruplex DNA, Htel-G4-DNA and Htel-3-G4-DNA were examined by Fluorescence and CD spectroscopic methods. In the Fluorescence emission spectral analysis, the addition of ofloxacin induced significant quenching on the fluorescence emission of TO-G4-DNA complex. The fluorescence spectral analysis indicated that ofloxacin exhibited higher binding affinity and binding intensity to Htel-G4-DNA than Htel-3-G4-DNA. In the CD spectral analysis, the interaction with ofloxacin did not disturb the characteristic absorption of Htel-G4-DNA at 290 nm corresponding to its antiparallel form, and only slightly increased the positive absorption at 270 nm as shoulder peak, which suggests the antiparallel structure of G-quadruplex can remain stable in the presence of ofloxacin

scholarly journals DNA binding properties, histidine interaction and cytotoxicity studies of water soluble ruthenium(ii) terpyridine complexes

2016 ◽  
Vol 45 (11) ◽  
pp. 4633-4646 ◽  
Author(s):  
Dejan Lazić ◽  
Aleksandar Arsenijević ◽  
Ralph Puchta ◽  
Živadin D. Bugarčić ◽  
Ana Rilak
Keyword(s):  
Dna Binding ◽  
Competitive Binding ◽  
Water Soluble ◽  
Binding Studies ◽  
Binding Properties ◽  
Cytotoxicity Studies ◽  
Vis Spectroscopy ◽  
Spectroscopy Studies ◽  
Ct Dna ◽  
Dna Binding Properties

UV-Vis spectroscopy studies, viscosity measurements and competitive binding studies with EB have revealed the ability of the complexes to bind to CT DNA covalently through N7 of guanine residues and non-covalently through intercalation.

scholarly journals Exploring the Interaction of Curaxin CBL0137 with G-Quadruplex DNA Oligomers

2021 ◽  
Vol 22 (12) ◽  
pp. 6476
Author(s):  
Sabrina Dallavalle ◽  
Luce M. Mattio ◽  
Roberto Artali ◽  
Loana Musso ◽  
Anna Aviñó ◽  
...  
Keyword(s):  
Dna Binding ◽  
31P Nmr ◽  
Antitumor Activities ◽  
Binding Properties ◽  
Dna Oligomers ◽  
Quadruplex Dna ◽  
Dna Targeting ◽  
G Quadruplex ◽  
Dna Binding Properties ◽  
Insight Into

Curaxins and especially the second-generation derivative curaxin CBL0137 have important antitumor activities in multiple cancers such as glioblastoma, melanoma and others. Although most of the authors suggest that their mechanism of action comes from the activation of p53 and inactivation of NF-kB by targeting FACT, there is evidence supporting the involvement of DNA binding in their antitumor activity. In this work, the DNA binding properties of curaxin CBL0137 with model quadruplex DNA oligomers were studied by 1H NMR, CD, fluorescence and molecular modeling. We provided molecular details of the interaction of curaxin with two G-quadruplex structures, the single repeat of human telomere d(TTAGGGT)4 and the c-myc promoter Pu22 sequence. We also performed 1H and 31P NMR experiments were also performed in order to investigate the interaction with duplex DNA models. Our data support the hypothesis that the interaction of curaxin with G-quadruplex may provide a novel insight into the DNA-binding properties of CBL0137, and it will be helpful for the design of novel selective DNA-targeting curaxin analogues.

The effect of isomerism and other structural variations on the G-quadruplex DNA-binding properties of some nickel Schiff base complexes

2020 ◽  
Vol 49 (30) ◽  
pp. 10360-10379 ◽  
Author(s):  
Son Q. T. Pham ◽  
Christopher Richardson ◽  
Celine Kelso ◽  
Anthony C. Willis ◽  
Stephen F. Ralph
Keyword(s):  
Schiff Base ◽  
Dna Binding ◽  
Schiff Base Complexes ◽  
Structural Variations ◽  
Binding Properties ◽  
Quadruplex Dna ◽  
G Quadruplex ◽  
Dna Binding Properties ◽  
Binding Behaviour

Changing the position of pendant groups on nickel Schiff base complexes can alter their binding behaviour towards quadruplex DNA.

Synthesis, Characterization, DNA Binding, and Photocleavage of [Ru(bpy)2(MFIP)]2+ and [Ru(phen)2(MFIP)]2+

2008 ◽  
Vol 61 (9) ◽  
pp. 725 ◽  
Author(s):  
Lifeng Tan ◽  
Sheng Zhang ◽  
Xiaohua Liu ◽  
Yue Xiao
Keyword(s):  
Mass Spectrometry ◽  
Dna Binding ◽  
1H Nmr Spectroscopy ◽  
Binding Properties ◽  
Experimental Conditions ◽  
Spectrophotometric Methods ◽  
Calf Thymus ◽  
Pbr322 Dna ◽  
Ct Dna ◽  
Dna Binding Properties

The new ligand 2-(5-methyl-furan-2-yl)imidazo[4,5-f][1, 10]phenanthroline (MFIP) and its complexes [Ru(bpy)2(MFIP)]2+ 1 (bpy = 2,2′-bipyridine) and [Ru(phen)2(MFIP)]2+ 2 (phen = 1,10-phenanthroline) were synthesized and characterized by elemental analysis, mass spectrometry, and 1H NMR spectroscopy. The DNA binding properties of the two complexes were investigated by different spectrophotometric methods and viscosity measurements. The results suggest that both complexes bind to calf thymus DNA (CT-DNA) through intercalation, and both complexes can enantioselectively interact with CT-DNA. The Λ enantiomers of both complexes are slightly predominant for binding to CT-DNA over the Δ enantiomer. When irradiated at 400 nm, the two complexes promote the photocleavage of pBR322 DNA, and complex 2 cleaves DNA more effectively than complex 1 under comparable experimental conditions. Furthermore, mechanism studies reveal that singlet oxygen (1O2) plays a significant role in the photocleavage.

DNA-Binding Properties of Iron(II) Mixed-Ligand Complexes Containing 1,10-Phenanthroline and Dipyrido[3,2-a:2’,3’-c]phenazine

2004 ◽  
Vol 59 (3) ◽  
pp. 310-318 ◽  
Author(s):  
◽  
Karna Wijaya ◽  
Daryono H. Tjahjono ◽  
Naoki Yoshioka ◽  
Hidenari Inoue
Keyword(s):  
Dna Binding ◽  
Bathochromic Shift ◽  
Mixed Ligand Complex ◽  
Visible Region ◽  
Spectrophotometric Titration ◽  
Mixed Ligand ◽  
Ligand Complex ◽  
Binding Properties ◽  
Ct Dna ◽  
Dna Binding Properties

An iron(II) mixed-ligand complex with 1,10-phenanthroline (phen) and dipyrido[3,2-a:2’,3’- c]phenazine (dppz), [Fe(phen)2(dppz)]2+, has been synthesized. The DNA-binding properties of the mixed-ligand complex have been studied in terms of equilibrium binding constant, thermodynamic parameter, thermal denaturation as well as Pfeiffer effect upon binding to DNA. The spectrophotometric titration of [Fe(phen)2(dppz)]2+ with calf thymus DNA (ct-DNA) has shown that the iron(II) mixed-ligand complex binds effectively to ct-DNA in an intercalation mode as indicated by remarkable hypochromicity (ca. 36%) and moderate bathochromic shift (8 nm) of the absorption spectra. This intercalative mode is supported by a significant increase (Δ Tm = 21 °C) in the melting temperature (Tm) of ct-DNA at R([complex]/[ct-DNA]) = 1.5. The binding of [Fe(phen)2(dppz)]2+ to ct-DNA is entropically driven as characterized by a positive enthalpy change and a large negative TΔ S term. An intense CD signal in the UV and visible region develops upon addition of ct-DNA to the racemate solution of [Fe(phen)2(dppz)]2+. This has revealed that a shift in diastereomeric inversion equilibrium takes place in the solution to yield an excess of one enantiomer of the DNA-iron(II) complex (Pfeiffer effect). The striking resemblance of the CD spectral profiles to those of the corresponding Δ -enantiomer indicates that Δ -[Fe(phen)2(dppz)]2+ is preferentially bound to ct-DNA

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