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<p>Three diphenylamino-thiazole donor-π-acceptor Schiff-base chromophores <b>5a-5c</b> were designed and synthesized to explore their photophysical properties and anticancer potential. The synthesized structures were characterized by FTIR and <sup>1</sup>H/<sup>13</sup>C NMR, and mass spectrometry. UV-Vis studies revealed pronounced positive solvatochromism (λ<sub>max</sub> = 406–470&#xa0;nm), consistent with efficient intramolecular charge transfer, and supported by density functional theory calculations. The chromophores exhibited strong visible emission (529–594&#xa0;nm) with large Stokes shifts (≈ 4.3–5.6 × 103&#xa0;cm<sup>− 1</sup>), indicating important excited-state relaxation. Kamlet-Taft analysis identified solvent dipolarity/polarizability and hydrogen-bond acceptor ability as dominant factors governing solvatochromism (R<sup>2</sup> = 0.977–0.983). Time-dependent density functional theory calculations reproduced the experimental spectra, confirming HOMO→LUMO π→π* Intramolecular Charge Transfer transitions and effective donor-acceptor electronic communication. Cytotoxic evaluation revealed against HT-29, MCF-7, and HepG2 cell lines, with chromophore <b>5b</b> showing the highest potency (IC<sub>50</sub> = 11.30 ± 0.61–16.46 ± 0.37 µM), comparable to Sorafenib, while maintaining low toxicity toward WI-38 normal cells, indicating acceptable selectivity. Molecular docking revealed moderate binding affinities, particularly for chromophore <b>5a</b> (S = -7.05&#xa0;kcal/mol), surpassing the reference drug and suggesting a preliminary inhibitory scaffold. Moreover, in silico pharmacokinetic analysis indicated acceptable drug-likeness, with satisfactory molecular weight, lipophilicity (LogP ≈ 4.0-4.7), TPSA (50.9–96.8 Å2), and good predicted oral bioavailability. Overall, these in vitro findings identify diphenylamino-thiazole chromophores, particularly <b>5b</b> and <b>5a</b>, as promising candidates for further development as preclinical investigation with integrated optoelectronic functionality. </p> Graphical Abstract <p></p>

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Rational Design of Diphenylamino-Thiazole Donor-π-Acceptor Schiff Base Chromophores: Solvatochromic Fluorescence, TD-DFT Insights, and Cytotoxic Activity

  • 期刊论文

  • 发表日期：

    2026年6月19日

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  • Maryam Alshahrani,
  • Shadiah Albalawi,
  • Sitah Almotiry,
  • Sara A. Alqarni,
  • Samar J. Almehmadi,
  • Matokah M. Abualnaja,
  • Hana M. Abumelha,
  • Nashwa M. El-Metwaly

摘要

Three diphenylamino-thiazole donor-π-acceptor Schiff-base chromophores 5a-5c were designed and synthesized to explore their photophysical properties and anticancer potential. The synthesized structures were characterized by FTIR and 1H/13C NMR, and mass spectrometry. UV-Vis studies revealed pronounced positive solvatochromism (λmax = 406–470 nm), consistent with efficient intramolecular charge transfer, and supported by density functional theory calculations. The chromophores exhibited strong visible emission (529–594 nm) with large Stokes shifts (≈ 4.3–5.6 × 103 cm− 1), indicating important excited-state relaxation. Kamlet-Taft analysis identified solvent dipolarity/polarizability and hydrogen-bond acceptor ability as dominant factors governing solvatochromism (R2 = 0.977–0.983). Time-dependent density functional theory calculations reproduced the experimental spectra, confirming HOMO→LUMO π→π* Intramolecular Charge Transfer transitions and effective donor-acceptor electronic communication. Cytotoxic evaluation revealed against HT-29, MCF-7, and HepG2 cell lines, with chromophore 5b showing the highest potency (IC50 = 11.30 ± 0.61–16.46 ± 0.37 µM), comparable to Sorafenib, while maintaining low toxicity toward WI-38 normal cells, indicating acceptable selectivity. Molecular docking revealed moderate binding affinities, particularly for chromophore 5a (S = -7.05 kcal/mol), surpassing the reference drug and suggesting a preliminary inhibitory scaffold. Moreover, in silico pharmacokinetic analysis indicated acceptable drug-likeness, with satisfactory molecular weight, lipophilicity (LogP ≈ 4.0-4.7), TPSA (50.9–96.8 Å2), and good predicted oral bioavailability. Overall, these in vitro findings identify diphenylamino-thiazole chromophores, particularly 5b and 5a, as promising candidates for further development as preclinical investigation with integrated optoelectronic functionality.

Graphical Abstract