Acting as a Molecular Tailor: Dye Structural Modifications for Improved Sensitivity toward Lysophosphatidic Acids Sensing

Nicolas Fontaine; Lara Harter; André Marette; Denis Boudreau

doi:10.1021/acsomega.2c06420

Acting as a Molecular Tailor: Dye Structural Modifications for Improved Sensitivity toward Lysophosphatidic Acids Sensing

ACS Omega. 2022 Dec 28;8(1):1067-1078. doi: 10.1021/acsomega.2c06420. eCollection 2023 Jan 10.

Authors

Nicolas Fontaine^{1

2}, Lara Harter^{1

2}, André Marette^{3

4}, Denis Boudreau^{1

2}

Affiliations

¹ Department of Chemistry, Université Laval, 1045 avenue de la Médecine, Québec, CanadaG1V 0A6.
² Center for Optics, Photonics and Lasers, Université Laval, 2375 rue de la Terrasse, Québec, CanadaG1V 0A6.
³ Quebec Heart and Lung Institute, Université Laval, 2725, chemin Sainte-Foy, Québec, CanadaG1V 4G5.
⁴ Institute of Nutrition and Functional Foods, Université Laval, 2440, boulevard Hochelaga, Québec, QC, CanadaG1V 0A6.

Abstract

Lysophosphatidic acids (LPA) are key biomarkers for several physiological processes, the monitoring of which can provide insights into the host's health. Common lab-based techniques for their detection are cumbersome, expensive, and necessitate specialized personnel to operate. LPA-sensitive fluorescent probes have been described, albeit for nonaqueous conditions, which impedes their use in biological matrices. In this paper, we explore in detail the influence of structure on the extent of aggregation-induced fluorescence quenching using specially synthesized styrylpyridinium dyes bearing structural adaptations to bestow them enhanced affinity toward LPA in aqueous media. Spectroscopic investigations supported by time-resolved fluorimetry revealed the contribution of excimer formation to the fluorescence quenching mechanism displayed by the fluorescent probes. Experimental observations of the influence of structure on detection sensitivity were supported by DFT calculations.