Fluorinated N-quinoxaline-based boron complexes: Synthesis, photophysical properties, and selective DNA/BSA biointeraction

Calheiro, Tainara P.; Franceschini, Steffany Z.; Nogara, Pablo Andrei; Rocha, João Batista Teixeira da; Zanatta, Nilo; Martins, Marcos A. P.; Iglesias, Bernardo A.; Bonacorso, Hélio G.

doi:10.1016/j.molstruc.2022.132444

Cited by 6 publications

(3 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The in silico molecular docking method is used to predict the binding poses and energies between small molecules and macromolecules. In this sense, the AutoDock Vina 1.1.1 program was used in this study, [48] according to previous studies [29,49,50] . The 3D structures of HSA was obtained from the Protein Data Bank (PDB) with the code 3B9 L, [50] and prepared for docking using the Chimera 1.8 [50] and AutoDockTools software [51] .…”

Section: Methodsmentioning

confidence: 99%

“…In this sense, the AutoDock Vina 1.1.1 program was used in this study, [48] according to previous studies. [29,49,50] The 3D structures of HSA was obtained from the Protein Data Bank (PDB) with the code 3B9 L, [50] and prepared for docking using the Chimera 1.8 [50] and AutoDockTools software. [51] Avogadro 1.1.1 [52] was used to build the 3D model of the compounds, followed by semi-empirical PM6 geometry optimization [53] (this method has been demonstrated able to reproduce the crystallographic data of derivatives).…”

Section: Molecular Docking Calculations With Hsamentioning

confidence: 99%

See 1 more Smart Citation

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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Molecular Docking Calculations With Hsamentioning

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

Self Cite

View full text Add to dashboard Cite

show abstract

“…The values of each UV band and the extinction coefficients of these bands are given in Table 1. Although maxima of emission spectra of such molecules are generally recorded at long wavelengths, [75,76] Daroudi et al recorded an intense emission band at 385 nm for acenaphtoquinoxaline which has considerable conjugation. [77] The fluorescence emission spectra of the molecules were also recorded for a 10 μM solution in methanol, and the solutions were excited at 270 nm (Figure 2 [b]).…”

Section: Preparation Of Quinoxaline-bridged Bis(benzimidazolium) Saltsmentioning

confidence: 99%

Applications of quinoxaline‐bridged bis(benzimidazolium) salts as ligand sources for the palladium‐catalyzed Suzuki and Heck cross‐coupling reactions in an aqueous medium

Düşünceli

Şahan

Kaloğlu

et al. 2022

J Chinese Chemical Soc

View full text Add to dashboard Cite

In the present work, quinoxaline-bridged bis(benzimidazolium) salts were prepared by the reaction of 2,3-bis(bromomethyl) quinoxaline and 1-substituted benzimidazole. The structures of the bis(benzimidazolium) salts were characterized by NMR, FT-IR, and elemental analysis techniques. Also, the photophysical properties of salts were investigated by UV-Vis absorption and fluorescence emission spectroscopy. Next, these quinoxaline bridged bis(benzimidazolium) salts were used as bidentate benzimidazol-2-ylidene ligand precursors in the palladium-catalyzed Suzuki-Miyaura and Mizoroki-Heck cross-couplings. These salts exhibited moderate-to-high activity in the palladium-catalyzed cross-coupling reactions.

show abstract

Synthesis, thermal, solution and solid-state emission properties of 1,1-difluoro-3,6-diaryl-1H-1λ4,8λ4-[1,3,4]oxadiazolo[3,2-c][1,3,5,2]oxadiazaborinines

Diniz

Kappenberg²,

Vieira³

et al. 2022

Dyes and Pigments

View full text Add to dashboard Cite

Fluorinated N-quinoxaline-based boron complexes: Synthesis, photophysical properties, and selective DNA/BSA biointeraction

Cited by 6 publications

References 49 publications

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

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

Applications of quinoxaline‐bridged bis(benzimidazolium) salts as ligand sources for the palladium‐catalyzed Suzuki and Heck cross‐coupling reactions in an aqueous medium

Synthesis, thermal, solution and solid-state emission properties of 1,1-difluoro-3,6-diaryl-1H-1λ4,8λ4-[1,3,4]oxadiazolo[3,2-c][1,3,5,2]oxadiazaborinines

Contact Info

Product

Resources

About