Premium
Mechanochemistry as a Sustainable Method for the Preparation of Fluorescent Ugi BODIPY Adducts
Author(s) -
PérezVenegas Mario,
Arbeloa Teresa,
Bañuelos Jorge,
LópezArbeloa Iñigo,
LozoyaPérez Nancy E.,
Franco Bernardo,
MoraMontes Héctor M.,
BelmonteVázquez José L.,
BautistaHernández Claudia I.,
PeñaCabrera Eduardo,
Juaristi Eusebio
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001267
Subject(s) - bodipy , chemistry , fluorescence , mechanochemistry , fluorescence microscope , flow cytometry , biophysics , candida albicans , staining , adduct , photochemistry , nanotechnology , combinatorial chemistry , organic chemistry , microbiology and biotechnology , medicine , physics , materials science , pathology , quantum mechanics , biology
Mechanochemistry, that is, the use of mechanical energy produced by milling or grinding to perform chemical transformations, was used as a green strategy using a minimal amount of solvent for the preparation of highly valuable formyl functionalized BODIPY dyes. The electronic properties of the meso ‐aryl group play a key role in the fluorescence response of the adducts resulting from the Ugi reaction. Such an understanding of the molecular structure‐fluorescence interplay explains the brightness of these dyes in the cellular media monitored by fluorescence imaging. In the present report, we provide flow cytometry and fluorescence microscopy evidence that the novel dyes efficiently stain peripheral blood mononuclear cells (PBMCs) and Candida albicans cells without disturbing cell integrity. Moreover, it is demonstrated that by staining C. albicans cells, we can monitor the early and late steps of phagocytosis, using human monocyte‐derived macrophages. The dye series presented herein represent a novel application for formyl functionalized BODIPYs, expanding their applications in monitoring biological processes.