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<p><i>N</i>-acylmelatonins (NAMs), a class of fatty acid amides featuring melatonin as the polar head group, demonstrate significant biomedical potential. In this study, a homologous series of saturated NAMs (<i>n</i> = 9–18) were synthesized and fully characterized <i>via</i> FTIR, NMR and HRMS. The biophysical self-assembly behaviour was assessed by powder X-ray diffraction and fluorescence spectroscopy. The <i>d</i>-spacing determined from PXRD increases linearly with an increment of ~ 0.90 Å per CH₂ group, suggesting that the NAMs adopt a tilted bilayer structure. Fluorescence spectroscopy was employed to measure the critical micellar concentrations (CMCs) of NAMs by monitoring the spectral changes of 8-anilinonaphthalene-1-sulfonate (ANS). Fluorescence emission and lifetime measurements of NAMs show a red-shift (~ 10&#xa0;nm) in emission maxima and a 2.4-fold emission intensity enhancement due to the hydrophobic acyl chain. Antioxidant properties, determined by DPPH radical scavenging assays, increased with concentration, showcasing potent activity. Notably, NAMs exhibited enhanced antimicrobial efficacy against clinically relevant bacterial and fungal strains, with minimum inhibitory concentrations comparable to standard drugs. <i>In vitro</i> anticancer screening revealed significant cytotoxicity against multiple human cancer cell lines, particularly with medium-chain NAMs. These findings highlight the broad-spectrum therapeutic potential of NAMs, driven by variable acyl chain length, self-assembly characteristics and strong biological applications.</p> Graphical abstract <p></p>

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Homologous series of N-acylmelatonins: synthesis, biophysical studies, enhanced antioxidant, antimicrobial and anticancer activities

  • 期刊论文

  • 发表日期：

    2026年5月28日

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  • Surendra Pothuraju,
  • Arya Jyothibabu Sajila,
  • Ravi Kanth Kamlekar

摘要

N-acylmelatonins (NAMs), a class of fatty acid amides featuring melatonin as the polar head group, demonstrate significant biomedical potential. In this study, a homologous series of saturated NAMs (n = 9–18) were synthesized and fully characterized via FTIR, NMR and HRMS. The biophysical self-assembly behaviour was assessed by powder X-ray diffraction and fluorescence spectroscopy. The d-spacing determined from PXRD increases linearly with an increment of ~ 0.90 Å per CH₂ group, suggesting that the NAMs adopt a tilted bilayer structure. Fluorescence spectroscopy was employed to measure the critical micellar concentrations (CMCs) of NAMs by monitoring the spectral changes of 8-anilinonaphthalene-1-sulfonate (ANS). Fluorescence emission and lifetime measurements of NAMs show a red-shift (~ 10 nm) in emission maxima and a 2.4-fold emission intensity enhancement due to the hydrophobic acyl chain. Antioxidant properties, determined by DPPH radical scavenging assays, increased with concentration, showcasing potent activity. Notably, NAMs exhibited enhanced antimicrobial efficacy against clinically relevant bacterial and fungal strains, with minimum inhibitory concentrations comparable to standard drugs. In vitro anticancer screening revealed significant cytotoxicity against multiple human cancer cell lines, particularly with medium-chain NAMs. These findings highlight the broad-spectrum therapeutic potential of NAMs, driven by variable acyl chain length, self-assembly characteristics and strong biological applications.

Graphical abstract