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Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes.
Sodre, Elaine R; Guido, Bruna C; de Souza, Paulo E N; Machado, Daniel F S; Carvalho-Silva, Valter H; Chaker, Juliano A; Gatto, Claudia C; Correa, Jose R; Fernandes, Talita de A; Neto, Brenno A D.
Afiliación
  • Sodre ER; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • Guido BC; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • de Souza PEN; Laboratory of Software and Instrumentation in Applied Physics and Laboratory of Electron Paramagnetic Resonance, Institute of Physics, Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-970, Brazil.
  • Machado DFS; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • Carvalho-Silva VH; Divisão de Modelagem de Transformações Físicas e Químicas, Grupo de Química Teo'rica e Estrutural de Ana'polis, Centro de Pesquisa e Pos-Graduação, Universidade Estadual de Goia's,, Ana'polis, Goia's 75001-970, Brazil.
  • Chaker JA; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • Gatto CC; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • Correa JR; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • Fernandes TA; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
  • Neto BAD; Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70904-900, Brazil.
J Org Chem ; 85(19): 12614-12634, 2020 10 02.
Article en En | MEDLINE | ID: mdl-32876447
An aggregation-induced emission enhancement (AIEE) effect in fluorescent lipophilic 2,1,3-benzothiadiazole (BTD) derivatives and their organic nanoaggregates were studied. A set of techniques such as single-crystal X-ray, dynamic light scattering (DLS), electron paramagnetic resonance (EPR), UV-vis, fluorescence, and density functional theory (DFT) calculations have been used to decipher the formation/break (kinetics), properties, and dynamics of the organic nanoaggregates of three BTD small organic molecules. An in-depth study of the excited-state also revealed the preferential relaxation emissive pathways for the BTD derivatives and the dynamics associated with it. The results described herein, for the first time, explain the formation of fluorescent BTD nanoaggregate derivatives and allow for the understanding of their dynamics in solution as well as the ruling forces of both aggregation and break processes along with the involved equilibrium. One of the developed dyes could be used at a nanomolar concentration to selectively stain lipid droplets emitting an intense and bright fluorescence at the red channel. The other two BTDs could also stain lipid droplets at very low concentrations and were visualized preferentially at the blue channel.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Tiadiazoles / Colorantes Fluorescentes Idioma: En Revista: J Org Chem Año: 2020 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Tiadiazoles / Colorantes Fluorescentes Idioma: En Revista: J Org Chem Año: 2020 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos