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Redox Center Modification of Lapachones towards the Synthesis of Nitrogen Heterocycles as Selective Fluorescent Mitochondrial Imaging Probes
Author(s) -
dos Santos Fabíola S.,
Dias Gleiston G.,
de Freitas Rossimiriam P.,
Santos Lucas S.,
de Lima Guilherme F.,
Duarte Hélio A.,
de Simone Carlos A.,
Rezende Lidia M. S. L.,
Vianna Monique J. X.,
Correa José R.,
Neto Brenno A. D.,
da Silva Júnior Eufrânio N.
Publication year - 2017
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.201700227
Subject(s) - chemistry , fluorescence , phenazine , imidazole , mitochondrion , combinatorial chemistry , naphthoquinone , membrane , biophysics , biochemistry , organic chemistry , physics , quantum mechanics , biology
We describe herein a synthetic strategy for the synthesis of new fluorescent imidazole and phenazine derivatives synthesized from lapachol, a naturally occurring naphthoquinone isolated from Tabebuia species (ipê tree). The photophysical properties and computational details of these compounds have been studied, aiming at gaining a complete understanding of the potential of these derivatives as probes capable of staining mitochondria selectively. Cell imaging experiments proved the capacity of the imidazole derivatives as selective fluorescent mitochondrial imaging probes. These heterocycles present the same staining patterns as MitoTracker Red, corroborating the potential of these compounds as new mitochondria markers permeable to the cell membrane.