Rational Design of Cost-Effective 4-Styrylcoumarin Fluorescent Derivatives for Biomolecule Labeling

Molecules. 2023 Sep 27;28(19):6822. doi: 10.3390/molecules28196822.

Abstract

Fluorescent labels are key tools in a wide range of modern scientific applications, such as fluorescence microscopy, flow cytometry, histochemistry, direct and indirect immunochemistry, and fluorescence in situ hybridization (FISH). Small fluorescent labels have important practical advantages as they allow maximizing the fluorescence signal by binding multiple fluorophores to a single biomolecule. At present, the most widely used fluorescent labels available present small Stokes shifts and are too costly to be used in routine applications. In this work we present four new coumarin derivatives, as promising and inexpensive fluorescent labels for biomolecules, obtained through a cost-effective, efficient, and straightforward synthetic strategy. Density functional theory and time-dependent density functional theory calculations of the electronic ground and lowest-lying singlet excited states were carried out in order to gain insights into the observed photophysical properties.

Keywords: 4-styrylcoumarin derivatives; biomolecules; coumarin; fluorescent labels.

MeSH terms

  • Cost-Benefit Analysis
  • Fluorescent Dyes* / chemistry
  • In Situ Hybridization, Fluorescence

Substances

  • Fluorescent Dyes

Grants and funding

The authors acknowledge financial support to FCT—Foundation for Science and Technology, I.P.—within the scope of the projects UIDB/04449/2020 (HERCULES Lab), UIDB/04033/2020 (CITAB), and ART3mis (2022.07303.PTDC/FCT) and the Old Goa Revelations project (2022.10305.PTDC/FCT) and also through the Ph.D. Grant UI/BD/153584/2022 (R.E.). The authors additionally acknowledge the City University of Macau endowment to the Sustainable Heritage Chair and Sino-Portugal Joint Laboratory of Cultural Heritage Conservation Science, supported by the Belt and Road Initiative and the projects UIDB/50006/2020 and UIDP/50006/2020 (LAQV-REQUIMTE).