Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study

Assaleh, Mohamed H.; Božić, Aleksandra; Bjelogrlić, Snežana K.; Milošević, Maja; Simić, Milena; Marinković, Aleksandar D.; Cvijetić, Ilija N.

doi:10.1007/s11224-019-01371-4

Cited by 9 publications

(4 citation statements)

References 44 publications

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“…All these processes can be quantitatively examined using quantum chemical calculations, where DFT methodology proved to be particularly useful for an accurate prediction of thermodynamic data at a moderate computational cost. This methodology proved to be a useful tool for studying the antioxidant properties of many polyphenols and the design of novel antioxidants [14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer

et al. 2021

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Humulones and iso-humulones are potent natural antioxidants found in beer. In this study, density functional theory (DFT) method was applied for elucidating the structure-antioxidant activity relationship and molecular mechanism of antioxidant activity of eight bioactive humulones previously identified in different beer samples: isoxanthohumol, (R)-and (S)-adhumulone, cisand trans-iso-adhumulone, cisand trans-iso-n-humulone, and desdimetyhyl-octahydro-isocohumulone. The calculated bond dissociation enthalpies (BDEs) suggest that desdimethyloctahydro-iso-cohumulone was the most potent compound with BDEs 5.1 and 23.9 kJ/mol lower compared to the values for resveratrol in gas phase and water, respectively. The enolic -OH is the most reactive site for hydrogen atom transfer (HAT). The presence of β-keto group with respect to enolic -OH diminishes the HAT potency via the formation of a strong intramolecular hydrogen bond. Another common antioxidant mechanism, single electron transfer followed by proton transfer (SET-PT), is only feasible for isoxanthohumol. The results of this study indicate a strong correlation between the increased antioxidant activity of beer products and the higher content of reduced iso-α-acids.

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Section: Introductionmentioning

confidence: 99%

DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer

et al. 2021

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“…The synthesis, characterization, and isomerism of thiocarbohydrazones 1–4 were reported in our previous paper [ 49 ].…”

Section: Methodsmentioning

confidence: 99%

Phenotypic Discovery of Thiocarbohydrazone with Anticancer Properties and Catalytic Inhibition of Human DNA Topoisomerase IIα

et al. 2023

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Phenotypic screening of α-substituted thiocarbohydrazones revealed promising activity of 1,5-bis(salicylidene)thiocarbohydrazide against leukemia and breast cancer cells. Supplementary cell-based studies indicated an impairment of DNA replication via the ROS-independent pathway. The structural similarity of α-substituted thiocarbohydrazone to previously published thiosemicarbazone catalytic inhibitors targeting the ATP-binding site of human DNA topoisomerase IIα prompted us to investigate the inhibition activity on this target. Thiocarbohydrazone acted as a catalytic inhibitor and did not intercalate the DNA molecule, which validated their engagement with this cancer target. A comprehensive computational assessment of molecular recognition for a selected thiosemicarbazone and thiocarbohydrazone provided useful information for further optimization of this discovered lead compound for chemotherapeutic anticancer drug discovery.

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“…Another proof that these compounds belong to mono-derivatives is expressed through the existence of a signal in the region between 4.70 and 4.91 ppm ( 1 H NMR spectra) for every synthesized compound, assigned to the NH 2 group. Some previous studies have shown that mTCHs have several possible solution structures including configurational (E or Z) isomers around imine bond and thione/thiol tautomers [25]. Careful analysis of the 1 H NMR spectra of the mTCHs concluded that all of the synthesized compounds in DMSO-d 6 solution exist in thione form and that there is no mixture of two isomers-E and Z.…”

Section: Characterization Of Monothiocarbohydrazonesmentioning

confidence: 96%

Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

et al. 2021

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Derivatives of thiocarbohydrazone studied so far have shown great biological activity such as antioxidant, antimicrobial, and anticancer. Most of these compounds are bis-substituted derivatives, while monothiocarbohydrazones are much less investigated. Еighteen monothiocarbohydrazones were synthesized and subjected to physicochemical characterization in order to facilitate the examination of their potential biological activity and application in future studies. The structure of synthesized derivatives was confirmed with NMR and FT-IR spectroscopy, and with elemental analysis. For one of the compounds, single-crystal X-ray diffraction analysis was performed. Specific and non-specific molecular interactions were interpreted by LSER principles, using Catalan's model. For additional information about the dominance and influence of the interactions presented, correlations with Hansen's solubility parameters were calculated. Influence of the type and position of the substituent on absorption maxima was determined with LFER (linear free-energy relationship) principles, using Hammett's equation. Acidity constants of the synthesized compounds were theoretically calculated and experimentally determined. Moreover, the excitation of a molecule by a photon of UV-Vis light was interpreted by time-dependent density functional theory (TD-DFT) calculations of UV absorption bands, and intramolecular charge transfer (ICT) was quantified by calculations of the charge transfer distances (D CT ).

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Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study

Cited by 9 publications

References 44 publications

DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer

DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer

Phenotypic Discovery of Thiocarbohydrazone with Anticancer Properties and Catalytic Inhibition of Human DNA Topoisomerase IIα

Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

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