Coordination of Zn(II), Pd(II) and Pt(II) with ligands derived from diformylpyridine and thiosemicarbazide: Synthesis, structural characterization, DNA/BSA binding properties and molecular docking analysis

Bessega, Tiago; Chaves, Otávio Augusto; Martins, Francisco Mainardi; Acunha, Thiago V.; Back, Davi F.; Iglesias, Bernardo A.; Oliveira, Gelson Manzoni de

doi:10.1016/j.ica.2019.119049

Cited by 22 publications

(9 citation statements)

References 48 publications

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“…Hydrogen atoms were added to the biomacromolecules following tautomeric states and ionization data inferred by GOLD 2020.2 software at pH 7.4. For DNA structure, the 10 Å radius around the center of mass of DT-20 was analyzed to explore the two main possible binding sites (major and minor grooves) [ 46 ]. On the other hand, for HSA structure 10 Å radius around the selected center of mass from the amino acid residue present in one of the three main binding pockets, more specifically Trp-214, Tyr-411, and Tyr-161 residues, for sites I, II, and III, respectively, was delimitated for molecular docking calculations.…”

Section: Methodsmentioning

confidence: 99%

Effects of Substituents on the Photophysical/Photobiological Properties of Mono-Substituted Corroles

et al. 2023

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The trans-A2B-corrole series was prepared starting with 5-(pentafluorophenyl)dipyrromethene, which was then reacted with respective aryl-substituted aldehyde by Gryko synthesis. It was further characterized by HRMS and electrochemical methods. In addition, we investigated experimental photophysical properties (absorption, emission by steady-state and time-resolved fluorescence) in several solvents and TDDFT calculations, aggregation, photostability and reactive oxygen species generation (ROS), which are relevant when selecting photosensitizers used in photodynamic therapy and many other photo-applications. In addition, we also evaluated the biomolecule-binding properties with CT-DNA and HSA by spectroscopy, viscometry and molecular docking calculations assays.

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Section: Methodsmentioning

confidence: 99%

Effects of Substituents on the Photophysical/Photobiological Properties of Mono-Substituted Corroles

et al. 2023

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“…The DNA structure presents two possible binding sites (major and minor grooves) [71] which were explored in the docking run. On the other hand, BSA structure presents three main binding pockets which also were explored via in silico calculations (subdomains IIA, IIIA and IB).…”

Section: Bsa-binding Assaysmentioning

confidence: 99%

“…On the other hand, BSA structure presents three main binding pockets which also were explored via in silico calculations (subdomains IIA, IIIA and IB). [71,72] Overall, GOLD 5.7 software optimizes the geometry for hydrogen bonding by allowing the rotation of hydroxyl and amino groups in the side chain and some nitrogenated bases or amino acid residues stayed flexible during the docking runs. The side chain rotamers have been defined according to the availability of the internal library.…”

Section: Bsa-binding Assaysmentioning

confidence: 99%

Synthesis, Photophysics, Computational Approaches, and Biomolecule Interactive Studies of Metalloporphyrins Containing Pyrenyl Units: Influence of the Metal Center

et al. 2022

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A classical methodology to design free-base meso-tetra-(1pyrenyl)porphyrin (H 2 TPyrP) and their corresponding metalloporphyrins containing Zn(II), Cu(II), Ni(II), Co(III), and Mn(III) was described. These porphyrins were characterized in terms of structure, photophysical, and interactions profile with calfthymus deoxyribonucleic acid (CT-DNA) and bovine serum albumin (BSA). H 2 TPyrP exhibited five characteristic bands in the visible wavelength: Soret (432 nm) and Q-bands (520-650 nm range), while the metalloporphyrins showed some spectrum shifts according to the nature of the ion, which were also explored by time-dependent density functional theory (TD-DFT) calculations. The fluorescence and singlet oxygen quantum yield (Φ fl , Φ Δ , respectively) decreased with the presence of metal species in the porphyrin core. The porphyrins interact spontaneously via a ground-state association in the minor groove of CT-DNA following the increasing order of binding: CuTPyrP < H 2 TPyrP < CoTPyrP < MnTPyrP < NiTPyrP < ZnTPyrP, while for BSA the suitable complex geometry for Co(III) and Mn(III) complexes increased the binding capacity.

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“…Since derivatives showed significant absorption at the excitation wavelengths used for HSA binding studies, the inner filter correction was applied to the steady-state fluorescence data according to the literature. [46,47] Upon the inner filter correction in the fluorescence data to obtain quantitative information on the binding affinity of the interaction between HSA and derivatives studied here, the modified Stern-Volmer Equation (4) were applied, in which, F 0 and F are the steady-state fluorescence intensities of HSA in the absence and presence of compounds, respectively. The [Q], K SV , and k q are the derivative concentration, Stern-Volmer quenching constant, and bimolecular quenching rate constant, respectively.…”

Section: Hsa-binding Properties By Steady-state Emission Fluorescencementioning

confidence: 99%

Bromo‐Substituted Diazenyl‐pyrazolo[1,5‐a]pyrimidin‐2‐amines: Sonogashira Cross‐Coupling Reaction, Photophysical Properties, Bio‐interaction and HSA Light‐Up Sensor

et al. 2022

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A convenient synthesis of a broad series of thirteen examples of alkyne-spacer derivatives 2 from the well-known Sonogashira cross-coupling reaction on diazenyl-pyrazolo[1,5-a]pyrimidin-2amine compounds 1 is reported. The reactivity of heterocycles 1 due the presence of selected electron-donor (EDG) and electron-withdrawing (EWG) groups attached to different alkynes was evaluated. Also, the reactional versatility due the position variation of the bromo atom at the scaffolds 1 was also investigated. In general, derivatives presented strong absorption bands at the 250-500 nm optical window and UV to cyan emission properties. Also, the redox analysis was recorded by electrochemical cyclic voltammetry technique. For HSA biomacromolecule assays, spectroscopic studies by UV-Vis, steadystate and time-resolved emission fluorescence, and molecular docking calculations evidenced the ability of each compound to establish interactions with human serum albumin (HSA). Finally, the behavior presented for this new class of heterocycles makes them a promising tool as optical sensors for albumins.

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Coordination of Zn(II), Pd(II) and Pt(II) with ligands derived from diformylpyridine and thiosemicarbazide: Synthesis, structural characterization, DNA/BSA binding properties and molecular docking analysis

Cited by 22 publications

References 48 publications

Effects of Substituents on the Photophysical/Photobiological Properties of Mono-Substituted Corroles

Effects of Substituents on the Photophysical/Photobiological Properties of Mono-Substituted Corroles

Synthesis, Photophysics, Computational Approaches, and Biomolecule Interactive Studies of Metalloporphyrins Containing Pyrenyl Units: Influence of the Metal Center

Bromo‐Substituted Diazenyl‐pyrazolo[1,5‐a]pyrimidin‐2‐amines: Sonogashira Cross‐Coupling Reaction, Photophysical Properties, Bio‐interaction and HSA Light‐Up Sensor

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