Synthesis, antioxidant and antimicrobial activity of carbohydrazones

Božić, Aleksandra; Filipović, Nenad R.; Novaković, Irena; Bjelogrlić, Snežana K.; Nikolić, Jasmina B.; Drmanić, Saša Ž.; Marinković, Aleksandar D.

doi:10.2298/jsc161220045b

Cited by 23 publications

(5 citation statements)

References 33 publications

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“…These values have provided considerable evidence for the formation of the compounds. These findings are consistent with previously reported values for related compounds [29,41,42].…”

Section: Synthesis and Characterizationsupporting

confidence: 94%

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Isatin/thiosemicarbohydrazone hybrids: Facile synthesis, and their evaluation as anti-proliferatıve agents and metabolıc enzyme inhibitors

Yakan,

Azam,

Kansız

et al. 2023

Bull. Chem. Soc. Eth.

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ABSTRACT. We are reporting a novel series of thiosemicarbazone derivatives derived from isatin (1-6), structural determination, and investigation of the inhibitory properties against proliferative, carbonic anhydrase, and cholinesterase enzymes. The anti-proliferative effects of the compounds were measured by XTT assay against MCF-7 and MDA-MB-231 cancerous cell lines. Compound 3 showed significant cytotoxic effects on both MCF-7 and MDA-MB-231 cell lines, with IC50 values of 8.19 μM and 23.41 μM, respectively. In addition, the compounds (1-6) inhibited the hCA I and II, their Ki values 2.01 ± 0.35 – 21.55 ± 2.56 and 1.24 ± 0.33 – 25.03 ± 5.48 µM, respectively. AChE was also successfully inhibited by these compounds (1-6), with Ki values ranging from 40.37 ± 8.23 to 125.43 ± 24.93 µM. The best Ki values for 3, 6, and 4 for α-glycosidase were 564.35 ± 72.06, 594.38 ± 52.04, and 683.437 ± 66.58 µM, respectively. Binding affinities were determined to be -6.697 kcal/mol, -8.251 kcal/mol, -9.932 kcal/mol, and -4.946 kcal/mol for hCA I, hCA II, AChE, and α-glucosidase enzymes, respectively. These findings reveal that the formed compounds containing isatin moieties were crucial in the enzyme inhibition. KEY WORDS: Isatin, Thiosemicarbazone, Anti-proliferative activity, Enzyme inhibition, Molecular docking Bull. Chem. Soc. Ethiop. 2023, 37(5), 1221-1236. DOI: https://dx.doi.org/10.4314/bcse.v37i5.14

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“…These values have provided considerable evidence for the formation of the compounds. These findings are consistent with previously reported values for related compounds [29,41,42].…”

Section: Synthesis and Characterizationsupporting

confidence: 94%

“…The proton signal of the methoxy group (-OCH3) was observed at 3.77 ppm as a singlet. Based on these observations, our findings are consistent with the previously published data [41,42].…”

Section: Synthesis and Characterizationsupporting

confidence: 94%

Isatin/thiosemicarbohydrazone hybrids: Facile synthesis, and their evaluation as anti-proliferatıve agents and metabolıc enzyme inhibitors

Yakan,

Azam,

Kansız

et al. 2023

Bull. Chem. Soc. Eth.

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“…In Figure 7B at t = 0 h, the coloration that appears as blue corresponds to low absorbance values. However, it is important to consider the potential impact of DMSO interference, which arises from the absorption of DMSO within the spectral range of 289-303 nm [75]. At t = 3 h in Figure 8B, detection of GF was not possible at 280 nm.…”

Section: The Behavior Of LV Diffusion Solvent Diffusion and Gel Forma...mentioning

confidence: 99%

Numerical Mechanistic Modelling of Drug Release from Solvent-Removal Zein-Based In Situ Gel

Senarat,

Pornsawad,

Lertsuphotvanit

et al. 2023

Pharmaceutics

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The development of effective drug delivery systems remains a focus of extensive research to enhance therapeutic outcomes. Among these, in situ forming gels (ISG) have emerged as a promising avenue for controlled drug release. This research focuses on the mathematical modeling of levofloxacin HCl (Lv) release from zein-based ISG using the cup method, aiming to mimic the environment of a periodontal pocket. The drug release behavior of the ISGs was investigated through experimental observations and numerical simulations employing forward and central difference formula. Notably, the experimental data for drug release from the 20% w/w zein-based ISG formulations closely aligned with the simulations obtained from numerical mechanistic modeling. In summary, 20% w/w zein-based ISG formulations demonstrated nearly complete drug release with the maximum drug concentration at the edge of the matrix phase values consistently around 100–105%, while 25% w/w zein-based ISG formulations exhibited somewhat lower drug release extents, with values ranging from 70–90%. Additionally, the rate of drug transport from the polymer matrix to the external phase influenced initial release rates, resulting in a slower release. The utilization of glycerol formal as a solvent extended drug release further than dimethyl sulfoxide, thanks to denser matrices formed by high-loading polymers that acted as robust barriers to solvent removal and drug diffusion. Furthermore, UV-vis imaging was utilized to visualize the matrix formation process and solvent diffusion within the ISGs. The imaging results offered valuable insights into the matrix formation kinetics, controlled drug release mechanisms, and the influence of solvent properties on drug diffusion. The combination of mathematical modeling and experimental visualization provides a comprehensive understanding of drug release from zein-based ISGs and offers a foundation for tailored drug delivery strategies.

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“…They are also used as versatile intermediates for synthesizing numerous compounds. They have shown a broad spectrum of chemical, biological and medicinal properties such as anti‐HIV, [11] antimicrobial [12] antiviral, [13] antibacterial, [14] anticonvulsant, [15] anticancer, [16] urease inhibitory activity, [17] antituberculosis, [18] cytotoxic activity, [19] and antioxidant agents [20–22] …”

Section: Introductionmentioning

confidence: 99%

“…They have shown a broad spectrum of chemical, biological and medicinal properties such as anti-HIV, [11] antimicrobial [12] antiviral, [13] antibacterial, [14] anticonvulsant, [15] anticancer, [16] urease inhibitory activity, [17] antituberculosis, [18] cytotoxic activity, [19] and antioxidant agents. [20][21][22] The ubiquitous enzyme superfamily of carbonic anhydrases (CAs; EC 4.2.1.1) plays a crucial role in most organisms/tissues due to its involvement in numerous physiologic and pathologic processes. [23] This is because it catalyzes the reaction that converts CO 2 into bicarbonate and protons, which is a straightforward but crucial reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors

Erdoğan,

Serdar Çavuş,

Muğlu

et al. 2023

Chemistry & Biodiversity

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Eleven new thiosemicarbazone derivatives (1‐11) were designed from nine different biologically and pharmacologically important isothiocyanate derivatives containing functional groups such as fluorine, chlorine, methoxy, methyl, and nitro at various positions of the phenyl ring, in addition to the benzyl unit in the molecular skeletal structure. First, their substituted‐thiosemicarbazide derivatives were synthesized from the treatment of isothiocyanate with hydrazine to synthesize the designed compounds. Through a one‐step easy synthesis and an eco‐friendly process, the designed compounds were synthesized with yields of up to 95% from the treatment of the thiosemicarbazides with aldehyde derivatives having methoxy and hydroxyl groups. The structures of the synthesized molecules were elucidated with elemental analysis and FT–IR, 1H NMR, and 13C NMR spectroscopic methods. The electronic and spectroscopic properties of the compounds were determined by the DFT calculations performed at the B3LYP/6‐311++G(2d,2p) level of theory, and the experimental findings were supported. They exhibited a highly potent inhibition effect on acetylcholinesterase (AChE) and carbonic anhydrases (hCAs) (KI values are in the range of 23.54±4.34 to 185.90±26.16 nM, 103.90±23.49 to 325.90 ±77.99 nM, and 86.15±18.58 to 287.70±43.09 nM for AChE, hCA I, and hCA II, respectively). Furthermore, molecular docking simulations were performed to explain each enzyme‐ligand complex's interaction.

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Synthesis, antioxidant and antimicrobial activity of carbohydrazones

Cited by 23 publications

References 33 publications

Isatin/thiosemicarbohydrazone hybrids: Facile synthesis, and their evaluation as anti-proliferatıve agents and metabolıc enzyme inhibitors

Isatin/thiosemicarbohydrazone hybrids: Facile synthesis, and their evaluation as anti-proliferatıve agents and metabolıc enzyme inhibitors

Numerical Mechanistic Modelling of Drug Release from Solvent-Removal Zein-Based In Situ Gel

Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors

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