Palladium Catalyst with Task-Specific Ionic Liquid Ligands: Intracellular Reactions and Mitochondrial Imaging with Benzothiadiazole Derivatives
Tipo
Artigo
Data de publicação
2019
Periódico
Journal of Organic Chemistry
Citações (Scopus)
22
Autores
Carvalho T.O.
Carvalho P.H.P.R.
Correa J.R.
Guido B.C.
Medeiros G.A.
Eberlin M.N.
Coelho S.E.
Domingos J.B.
Neto B.A.D.
Carvalho P.H.P.R.
Correa J.R.
Guido B.C.
Medeiros G.A.
Eberlin M.N.
Coelho S.E.
Domingos J.B.
Neto B.A.D.
Orientador
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Título de Volume
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Resumo
© 2019 American Chemical Society.A water-soluble and charge-tagged palladium complex (PdMAI) was found to function inside breast cancer live cells of the MCF-7 lineage as an efficient catalyst for cross-coupling reaction. PdMAI, bearing two ionophilic task-specific ionic liquids as ligands, efficiently catalyzed both in cellulo Suzuki and Buchwald-Hartwig amination reactions. For the first time, therefore, the Buchwald-Hartwig amination is described to occur inside the highly complex cellular environment. The 2,1,3-benzothiadiazole (BTD) core was used as the base for the syntheses, and two π-extended fluorescent derivatives (BTD-2APy) and (BTD-1AN), which were found to emit in the green and red channels, had impressive mitochondrial affinity. These chromophores allowed for selective mitochondrial imaging and tracking.
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Assuntos Scopus
2 ,1 ,3-Benzothiadiazole , Benzothiadiazole derivatives , Cellular environment , Cross coupling reactions , Efficient catalysts , Intracellular reactions , Palladium complexes , Task-specific ionic liquids