High Photostability in Nonconventional Coumarins with Far-Red/NIR Emission through Azetidinyl Substitution

The Journal of Organic Chemistry
Albert GandiosoVicente Marchán

Abstract

Replacement of electron-donating N,N-dialkyl groups with three- or four-membered cyclic amines (e.g., aziridine and azetidine, respectively) has been described as a promising approach to improve some of the drawbacks of conventional fluorophores, including low fluorescent quantum yields (ΦF) in polar solvents. In this work, we have explored the influence of azetidinyl substitution on nonconventional coumarin-based COUPY dyes. Two azetidine-containing scaffolds were first synthesized in four linear synthetic steps and easily transformed into far-red/NIR-emitting fluorophores through N-alkylation of the pyridine moiety. Azetidine introduction in COUPY dyes resulted in enlarged Stokes' shifts with respect to the N,N-dialkylamino-containing parent dyes, but the ΦF were not significantly modified in aqueous media, which is in contrast with previously reported observations in other fluorophores. However, azetidinyl substitution led to an unprecedented improvement in the photostability of COUPY dyes, and high cell permeability was retained since the fluorophores accumulated selectively in mitochondria and nucleoli of HeLa cells. Overall, our results provide valuable insights for the design and optimization of novel fluorophores operat...Continue Reading

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Citations

Apr 6, 2019·Physical Chemistry Chemical Physics : PCCP·Łukasz KielesińskiDaniel T Gryko
Jul 25, 2019·Chemistry : a European Journal·Olena VakuliukDaniel T Gryko
Nov 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jiahui MaHenning J Jessen
Jan 11, 2019·The Journal of Organic Chemistry·Anna RoviraVicente Marchán
Oct 8, 2021·Organic & Biomolecular Chemistry·Ignacio Muñoz RestaFrancisco Galindo
Nov 20, 2021·Journal of Medicinal Chemistry·Enrique Ortega-ForteVicente Marchán
Jan 12, 2022·Chemical Communications : Chem Comm·Kateryna V VygranenkoDaniel T Gryko

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