Synthesis and Antiproliferative Evaluation of 5′‐Arylchalcogenyl‐3‐(phenylselanyl‐triazoyl)‐thymidine

Quoos, Natália; Dornelles, Luciano; Buss, Julieti H.; Begnini, Karine R.; Collares, Tiago; Seixas, Fabiana Kömmling; Garcia, Fábio D.; Rodrigues, Oscar E. D.

doi:10.1002/slct.201904076

Cited by 4 publications

(1 citation statement)

References 31 publications

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“…Previous data from the group have demonstrated that new compounds formed by adding chalcogen atoms to the structure of commercial AZT were able to enhance the in vitro antioxidant and antitumor action of the hydride molecules [ 46 , 47 ]. In this context, it was reported that the presence of chalcogen in the molecule 5′-arylchalcogenyl-3-(phenylselanyl-triazoyl)-thymidine reduced the proliferative capacity of bladder cancer cells and amplified the activity of the compound [ 48 ]. Additional results revealed that in breast cancer cell line, AZT analogs containing tellurium were more effective in inhibiting tumor growth and showed lower cytotoxicity than the original antiretroviral molecule [ 46 ].…”

Section: Introductionmentioning

confidence: 99%

Antiviral Effect of 5′-Arylchalcogeno-3-aminothymidine Derivatives in SARS-CoV-2 Infection

Tucci,

da Rosa,

Rosa

et al. 2023

Molecules

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The understanding that zidovudine (ZDV or azidothymidine, AZT) inhibits the RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2 and that chalcogen atoms can increase the bioactivity and reduce the toxicity of AZT has directed our search for the discovery of novel potential anti-coronavirus compounds. Here, the antiviral activity of selenium and tellurium containing AZT derivatives in human type II pneumocytes cell model (Calu-3) and monkey kidney cells (Vero E6) infected with SARS-CoV-2, and their toxic effects on these cells, was evaluated. Cell viability analysis revealed that organoselenium (R3a–R3e) showed lower cytotoxicity than organotellurium (R3f, R3n–R3q), with CC50 ≥ 100 µM. The R3b and R3e were particularly noteworthy for inhibiting viral replication in both cell models and showed better selectivity index. In Vero E6, the EC50 values for R3b and R3e were 2.97 ± 0.62 µM and 1.99 ± 0.42 µM, respectively, while in Calu-3, concentrations of 3.82 ± 1.42 µM and 1.92 ± 0.43 µM (24 h treatment) and 1.33 ± 0.35 µM and 2.31 ± 0.54 µM (48 h) were observed, respectively. The molecular docking calculations were carried out to main protease (Mpro), papain-like protease (PLpro), and RdRp following non-competitive, competitive, and allosteric inhibitory approaches. The in silico results suggested that the organoselenium is a potential non-competitive inhibitor of RdRp, interacting in the allosteric cavity located in the palm region. Overall, the cell-based results indicated that the chalcogen-zidovudine derivatives were more potent than AZT in inhibiting SARS-CoV-2 replication and that the compounds R3b and R3e play an important inhibitory role, expanding the knowledge about the promising therapeutic capacity of organoselenium against COVID-19.

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Section: Introductionmentioning

confidence: 99%

Antiviral Effect of 5′-Arylchalcogeno-3-aminothymidine Derivatives in SARS-CoV-2 Infection

Tucci,

da Rosa,

Rosa

et al. 2023

Molecules

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Synthesis and Application of New Selanylfullerene Derivatives as Photosensitizers for Photodynamic Therapy

Soares,

Vargas,

Ravanello

et al. 2024

Chemistry An Asian Journal

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This study aims to describe the synthesis of a new class of selanylfullerene derivatives in a convergent strategy route, affording the desired products in a few steps and in good yields. C60 compounds were evaluated as photosensitizers to be used in photodynamic therapy (PDT) via the generation of singlet oxygen (1O2), using the chemical trapping method. The photooxidation of the chemical probe1,3‐diphenylisobenzofuran (DPBF) sensitized by selanylfullerenes followed a first‐order kinetic and the values of singlet oxygen quantum yields (ΦΔ) are appropriate for its use in PDT. The electronic absorption spectra, and the intersystem crossing tax rates for the most prominent synthesized compounds were calculated using the density functional theory and the Marcus electron transfer theory, with the theoretical results confirming the experimental findings.

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Synthesis, antioxidant and antitumoral activity of new 5′-arylchalcogenyl-3′-N-(E)-feruloyl-3′, 5′-dideoxy-amino-thymidine (AFAT) derivatives

et al. 2022

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Synthesis and Antiproliferative Evaluation of 5′‐Arylchalcogenyl‐3‐(phenylselanyl‐triazoyl)‐thymidine

Cited by 4 publications

References 31 publications

Antiviral Effect of 5′-Arylchalcogeno-3-aminothymidine Derivatives in SARS-CoV-2 Infection

Antiviral Effect of 5′-Arylchalcogeno-3-aminothymidine Derivatives in SARS-CoV-2 Infection

Synthesis and Application of New Selanylfullerene Derivatives as Photosensitizers for Photodynamic Therapy

Synthesis, antioxidant and antitumoral activity of new 5′-arylchalcogenyl-3′-N-(E)-feruloyl-3′, 5′-dideoxy-amino-thymidine (AFAT) derivatives

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