JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 71 No 2 (2026): Journal of The Chilean Chemical Society - 2nd Special Issue in Tribute to Professor Mario Silva (In Memoriam)
Original Research Papers

COMPUTATIONAL STUDY OF OXAZOLIDINOINDOLE-BASED CHROMOGENIC PROBES FOR Β-GALACTOSIDASE DETECTION

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  • Juan Carlos Santos,
  • Germán Barriga-González,
  • Carlos Escobar
Carlos Escobar
Universidad San Sebastian
Published September 22, 2026
Keywords
  • β-galactosidase detection,
  • DFT,
  • Fused oxazolidine,
  • Chromogenic probe,
  • NBO Second-order perturbation analysis
How to Cite
Santos, J. C., Barriga-González, G., & Escobar, C. (2026). COMPUTATIONAL STUDY OF OXAZOLIDINOINDOLE-BASED CHROMOGENIC PROBES FOR Β-GALACTOSIDASE DETECTION. Journal of the Chilean Chemical Society, 71(2), 6565-6568. Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/3092

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Abstract

This study investigates phenoxystyrenyl-oxazolidino-indole (POI)-based chromogenic probes for β-galactosidase detection from a computational perspective. The POI probe undergoes a pronounced UV–vis color change (from colorless to red) upon interaction with β-galactosidase, leading to the formation of a hydroxyethylindolium zwitterion. To elucidate the electronic processes behind this color change, we introduced -H, -CN, and -OCH3 substituents in the phenoxy moiety and analyzed their electronic properties using TD-DFT, NBO, ELF, and LOL methods. Our findings highlight the critical role of electron-withdrawing substituents in sensor response. The -CN group reduces electron delocalization, hindering the formation of the colored product, as confirmed by natural resonance theory (NRT), second-order perturbation, and topological analyses. Conversely, the -OCH3 substituent enhances delocalization, preserving the chromogenic response. NBO second-order perturbation analysis reveals an electronic delocalization pattern extending from the phenoxy to the indole through the styrenyl moiety. Electron-donating groups stabilize resonance forms, while electron-withdrawing groups, like the cyano group, decrease the number of resonance forms. Absorption transitions in the 400-550 nm region explain the characteristic red color of the hydroxyethylindolium zwitterion, involving HOMO–LUMO transitions in delocalized π-orbitals.

 

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