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An Experimental and Theoretical Study of Dye Properties of Thiophenyl Derivatives of 2-Hydroxy-1,4-naphthoquinone (Lawsone).

ABSTRACT: A prospective study of the dye properties of non-toxic lawsone thiophenyl derivatives, obtained using a green synthetic methodology allowed for the description of their bathochromic shifts in comparison to those of lawsone, a well-known natural pigment used as a colorant that recently also has aroused interest in dye-sensitized solar cells (DSSCs). These compounds exhibited colors close to red, with absorption bands in visible and UV wavelength range. The colorimetric study showed that these compounds exhibited a darker color than that of lawsone within a range of colors depending on the substituent in the phenyl ring. Computational calculations employing Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT), showed that the derivatives have lower excitation energies than lawsone, while the alignment of their frontier orbitals regarding the conduction bands of TiO₂ and ZnO and the redox potential of the electrolyte I^-/I₃^- suggests that they could be employed as sensitizers. The study of the interactions of the lawsone and a derivative with a TiO₂ surface model by different anchoring modes, showed that the adsorption is thermodynamically favored. Natural bond orbital (NBO) analysis indicates a two-center bonding (BD) O-Ti as the main interaction of the dyes with TiO₂.

SUBMITTER: Monroy-Cardenas M

PROVIDER: S-EPMC8509387 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Synthesis and Biological Evaluation of Thio-Derivatives of 2-Hydroxy-1,4-Naphthoquinone (Lawsone) as Novel Antiplatelet Agents.

Project description:We designed and synthesized in water, using conventional heating and microwave irradiation, new thio-derivatives of 2-hydroxy-1,4-naphthoquinone, a naturally occurring pigment known as lawsone or hennotannic acid, thus improving their antiplatelet activity with relevance to their potential future use in thrombus formation treatment. The structure-activity relationship showed that the thiophenyl moiety enhances the antiplatelet activity. Moreover, the position and nature of the substituent at the phenyl ring have a key effect on the observed biological activity. Compound 4 (2-((4-bromophenyl)thio)-3-hydroxynaphthalene-1,4-dione) was the most active derivative, presenting IC50 values for platelet aggregation inhibition of 15.03 ± 1.52 ?M for TRAP-6, and 5.58 ± 1.01 ?M for collagen. Importantly, no cytotoxicity was observed. Finally, we discussed the structure-activity relationships of these new lawsone thio-derivatives on inhibition of TRAP-6- and collagen-induced platelet aggregation.

| S-EPMC7417813 | biostudies-literature

Aromatase inhibitory activity of 1,4-naphthoquinone derivatives and QSAR study.

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| S-EPMC5547393 | biostudies-literature

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| S-EPMC4056940 | biostudies-literature

Synthesis and Antimicrobial Evaluation of 1,4-Naphthoquinone Derivatives as Potential Antibacterial Agents.

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Steroidal Molecular Rotors with 1,4-Diethynylphenylene Rotators: Experimental and Theoretical Investigations Toward Seeking Efficient Properties.

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| S-EPMC7604858 | biostudies-literature

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Project description:We report here a comparative theoretical and experimental study of four triazine-based hydrazone derivatives. The hydrazones are synthesized by a three step process from commercially available benzil and thiosemicarbazide. The structures of all compounds were determined by using the UV-Vis., FT-IR, NMR (1H and 13C) spectroscopic techniques and finally confirmed unequivocally by single crystal X-ray diffraction analysis. Experimental geometric parameters and spectroscopic properties of the triazine based hydrazones are compared with those obtained from density functional theory (DFT) studies. The model developed here comprises of geometry optimization at B3LYP/6-31G (d, p) level of DFT. Optimized geometric parameters of all four compounds showed excellent correlations with the results obtained from X-ray diffraction studies. The vibrational spectra show nice correlations with the experimental IR spectra. Moreover, the simulated absorption spectra also agree well with experimental results (within 10-20 nm). The molecular electrostatic potential (MEP) mapped over the entire stabilized geometries of the compounds indicated their chemical reactivates. Furthermore, frontier molecular orbital (electronic properties) and first hyperpolarizability (nonlinear optical response) were also computed at the B3LYP/6-31G (d, p) level of theory.

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Anti-Herpetic, Anti-Dengue and Antineoplastic Activities of Simple and Heterocycle-Fused Derivatives of Terpenyl-1,4-Naphthoquinone and 1,4-Anthraquinone.

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Project description:To examine the effect of hydrophobicity on the anticancer activity of 1,4-naphthoquinone derivatives, a series of compounds bearing a 2-O-alkyl-, 3-C-alkyl- or 2/3-N-morpholinoalkyl group were synthesized and evaluated for their anticancer activity against five human cancer cell lines in vitro. The cytotoxicity of these derivatives was assayed against HT-29, SW480, HepG2, MCF-7 and HL-60 cells by the MTT assay. Among them, 2-hydroxy-3-farnesyl-1,4-naphthoquinone (11a) was found to be the most cytotoxic against these cell lines. Our results showed that the effectiveness of compound 11a may be attributed to its suppression of the survival of HT-29. Secondly, in the Hoechst 33258 staining test, compound 11a-treated cells exhibited nuclear condensation typical of apoptosis. Additionally, cell cycle analysis by flow cytometry indicated that compound 11a arrested HT-29 cells in the S phase. Furthermore, cell death detected by Annexin V-FITC/propidium iodide staining showed that compound 11a efficiently induced apoptosis of HT-29 in a concentration-dependent manner. Taken together, compound 11a effectively inhibits colon cancer cell proliferation and may be a potent anticancer agent.

| S-EPMC6331847 | biostudies-other

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