Synthesis, characterization and crystal structures of two novel sulfa drug Schiff base ligands derived sulfonamide and molecular docking study

Salehi, Mehdi; Kubicki, Maciej; Galini, Masumeh; Jafari, Morad; Malekshah, Rahime Eshaghi

doi:10.1016/j.molstruc.2018.12.002

Cited by 38 publications

(14 citation statements)

References 21 publications

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“…30 The band occurring at 342 nm was attributed to the formation of a Schiff base complex on GNRs (curve d in Figures S5A and S7). 31,32 The FL intensity of GNRs-QDs@NU-901 decreased at 543 nm (Figure S5A, vial 1), owing to the FRET from QDs to GNRs (Figures S8 and S9). To further validate the FRET mechanism, the time-resolved fluorescence spectroscopies of QDs that coexisted with or without GNRs were compared.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Identification and Detection of Volatile Aldehydes as Lung Cancer Biomarkers by Vapor Generation Combined with Paper-Based Thin-Film Microextraction

Xia

Deng

2021

Anal. Chem.

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Accurate, sensitive, and selective on-spot screening of volatile aldehydes as lung cancer biomarkers is of vital significance for preclinical diagnosis and treatment guidance of cancers. However, the common methods of sensing biomarkers are limited by the fact that they are time-consuming, require professional personnel, and have complex matrixes. Here, we developed a smart vapor generation paper-based thin-film microextraction system capable of both sensitive on-field fluorescence detection and accurate surface-enhanced Raman spectroscopy (SERS) quantification of volatile benzaldehyde (BA) by utilizing stimuli-responsive core–shell gold nanorod (GNR) quantum dot (QD)-embedded metal–organic framework (MOF) structures. The amino-modified GNRs and carboxyl-capped QDs can directly assemble with each other by electrostatic interaction, which leads to an almost complete emission quenching of QDs. The addition of BA molecules destroys the GNRs-QD assemblies due to the Schiff base reactions between the amine group of 4-mercaptonoaniline and the aldehyde moiety of BA, resulting in the increase of the fluorescence and Raman signal of hybrid systems, which enables the visualization of BA with the naked eye. Moreover, the “cavity-diffusion” effect of porous MOF shells validates the selective concentration of gaseous BA molecules on the GNR surface, allowing the discrimination of BA in exhaled breath rapidly and precisely even at the sub-ppb level with excellent specificity against other volatile organic compounds. This study not only offers a versatile sensing platform for accurate discrimination of lung cancer from controls but also opens an avenue for the design of smart sensors for point-of-care applications.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Identification and Detection of Volatile Aldehydes as Lung Cancer Biomarkers by Vapor Generation Combined with Paper-Based Thin-Film Microextraction

Xia

Deng

2021

Anal. Chem.

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“…Molecular docking simulation was carried out for all compounds with DNA, ribonucleotide reductase, and topoisomerase II. Development of novel transition-metal-based drugs which bind DNA by noncovalent modes including major and minor groove binding, electrostatic effect between the negatively charged nucleic sugar–phosphate backbone and the positive or negative end of the compounds, and intercalation is priority (Yang et al., 2017 ; Salehi et al., 2019 ). DNA topoisomerase II inhibitors such as the anthracyclines (daunorubicin and doxorubicin) bind to the transient enzyme–DNA complex and inhibit the activity of DNA Topo2 enzyme and DNA replication (Arthur, 2019 ).…”

Section: Discussionmentioning

confidence: 99%

Synthesis and toxicity assessment of Fe ₃ O ₄ NPs grafted by ∼ NH ₂ -Schiff base as anticancer drug: modeling and proposed molecular mechanism through docking and molecular dynamic simulation

et al. 2020

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Superparamagnetic iron oxide nanoparticles have been synthesized using chain length of (3-aminopropyl) triethoxysilane for cancer therapy. First, we have developed a layer by layer functionalized with grafting 2,4-toluene diisocyanate as a bi-functional covalent linker onto a nano-Fe 3 O 4 support. Then, they were characterized by Fourier transform infrared, X-ray powder diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, and VSM techniques. Finally, all nanoparticles with positive or negative surface charges were tested against K562 (myelogenous leukemia cancer) cell lines to demonstrate their therapeutic efficacy by MTT assay test. We found that the higher toxicity of Fe 3 O 4 @SiO 2 @APTS $ Schiff base-Cu(II) (IC 50 : 1000 lg/mL) is due to their stronger in situ degradation, with larger intracellular release of iron ions, as compared to surface passivated NPs. For first time, the molecular dynamic simulations of all compounds were carried out afterwards optimizing using MMþ, Semi-empirical (AM1) and Ab-initio (STO-3G), Forcite Gemo Opt, Forcite Dynamics, Forcite Energy and CASTEP in Materials studio 2017. The energy (eV), space group, lattice parameters (Å), unit cell parameters (Å), and electron density of the predicted structures were taken from the CASTEP module of Materials Studio. The docking methods were used to predict the DNA binding affinity, ribonucleotide reductase, and topoisomerase II.

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“…[9] Schiff bases are the compounds bearing azomethine group (À HC=NÀ ) and can be synthesized from an amine and a carbonyl compound by nucleophilic addition under base catalysis, acid catalysis, or heat. [10] Similarly, since Schiff bases derived from a variety of heterocycles have numerous potential applications in various biological and pharmacological fields such as the sulfathiazoles, the attention of medicinal chemists is to attract constantly. The scaffold obtained by hybridization of sulfathiazoles with the azomethine unit has a higher potential in biological and pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

“…The scaffold obtained by hybridization of sulfathiazoles with the azomethine unit has a higher potential in biological and pharmacological activities. [10] In this context, the inhibition potencies of two benzenesulfonamide hybrids were explored on the eight enzymes including tyrosinase, α-glucosidase, cholesterol esterase after the structural and spectroscopic characterizations and the enzyme active sites of these hybrids were evaluated in the framework of the B3LYP/6-311 + + G(d,p) computations. [11] On the other hand, pyrene is a hydrophobic polycyclic aromatic hydrocarbon with well-known photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

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A novel pyrene-sulfathiazole-based potential drug candidate 3 was designed, successfully synthesized by a condensation reaction of pyrenecarboxaldehyde (1) with sulfathiazole (2) in good yield, and fully characterized by NMR, IR, UV-Vis, and HRMS spectroscopic techniques. The TD-DFT/B3LYP calculations displayed that the recorded peaks at 396, 377, 280, and 236 nm were due to the mainly n-π* and partially π-π* transitions that occurred on pyrene, azomethine, and sulfathiazole moieties. The NBO results disclosed that the electron delocalizations happened onto sulfathiazole, aromatic rings (pyrene and Ph-), and azomethine groups had the main responsibility of the lowering stabilization energy of compound 3. The NMR shifts were calculated by using the GIAO approaches in the DMSO phase and compared with the relevant data recorded. The thermodynamic and quantum chemical quantities were used for elucidating the physicochemical properties and reactivity behavior, in THF, DMSO, and water simulation environments. Accordingly, the calculated DM (D) and α (au) order of compound 3 were calculated in the order of vacuum < THF < DMSO < water, which indicated that the stability and thus reactivity of the compound strongly depended on the solvent environment. The FMO studies implied that the electron-donating possibility of compound 3 was dominant to the electron-accepting potency. In this work, the SMD version of IEFPCM was used in solvent media simulations.

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Synthesis, characterization and crystal structures of two novel sulfa drug Schiff base ligands derived sulfonamide and molecular docking study

Cited by 38 publications

References 21 publications

Identification and Detection of Volatile Aldehydes as Lung Cancer Biomarkers by Vapor Generation Combined with Paper-Based Thin-Film Microextraction

Identification and Detection of Volatile Aldehydes as Lung Cancer Biomarkers by Vapor Generation Combined with Paper-Based Thin-Film Microextraction

Synthesis and toxicity assessment of Fe ₃ O ₄ NPs grafted by ∼ NH ₂ -Schiff base as anticancer drug: modeling and proposed molecular mechanism through docking and molecular dynamic simulation

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

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Synthesis, characterization and crystal structures of two novel sulfa drug Schiff base ligands derived sulfonamide and molecular docking study

Cited by 38 publications

References 21 publications

Identification and Detection of Volatile Aldehydes as Lung Cancer Biomarkers by Vapor Generation Combined with Paper-Based Thin-Film Microextraction

Identification and Detection of Volatile Aldehydes as Lung Cancer Biomarkers by Vapor Generation Combined with Paper-Based Thin-Film Microextraction

Synthesis and toxicity assessment of Fe 3 O 4 NPs grafted by ∼ NH 2 -Schiff base as anticancer drug: modeling and proposed molecular mechanism through docking and molecular dynamic simulation

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

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Synthesis and toxicity assessment of Fe ₃ O ₄ NPs grafted by ∼ NH ₂ -Schiff base as anticancer drug: modeling and proposed molecular mechanism through docking and molecular dynamic simulation