Selective endocytic trafficking in live cells with fluorescent naphthoxazoles and their boron complexes

Dias, Gleiston G.; Rodrigues, Bernardo L.; Resende, Jarbas M.; Calado, Hállen Daniel Rezende; Simone, C. A. De; Silva, Valter H. C.; Neto, Brenno A. D.; Goulart, Marília Oliveira Fonseca; Ferreira, Fabricia da Rocha; Meira, Assuero Silva; Pessoa, Cláudia; Corrêa, José R.; Júnior, Eufrânio N. da Silva

doi:10.1039/c5cc02383a

Cited by 24 publications

(22 citation statements)

References 23 publications

(14 reference statements)

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“…The study of their optical properties reveals that they both display a dual E*/K* emission ( λ em =477/584 nm and 457/561 nm for 12 and 13 , respectively, in toluene). This feature was previously described for related naphthoxazole fluorophores . The K*/E* intensity ratio of the emission bands is much higher for 13 than 12 .…”

Section: Resultssupporting

confidence: 79%

On the Fine‐Tuning of the Excited‐State Intramolecular Proton Transfer (ESIPT) Process in 2‐(2′‐Hydroxybenzofuran)benzazole (HBBX) Dyes

Heyer

Benelhadj

Budzák

et al. 2017

Chemistry A European J

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Herein, a full investigation of the optical properties and first-principles calculations of a large series of original 2-(2'-hydroxybenzofuran)benzazole (HBBX) dyes is described. The electronic substitution on the π-conjugated core of the fluorophores and the nature of the heteroatom (O, S, N) was varied extensively to assess the necessary parameters to trigger a partial frustration of the excited-state intramolecular proton transfer (ESIPT) process, which results in the emission of both tautomers, that is, enol and keto (E* and K*). The optical properties, studied in solution and in the solid state, revealed the appearance of either an intense single K* or a dual E*/K* emission; a feature that is highly dependent on the electronic substitution (donating or accepting), the heteroelement, and the close environment. Subtle modifications of these parameters allowed the establishment of structure-property relationships that were successfully rationalized by first-principles calculations. In particular, the E*/K* emission intensity ratio was shown to be directly related to the free energies of the two emissive tautomers in the excited state.

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Section: Resultssupporting

confidence: 79%

On the Fine‐Tuning of the Excited‐State Intramolecular Proton Transfer (ESIPT) Process in 2‐(2′‐Hydroxybenzofuran)benzazole (HBBX) Dyes

Heyer

Benelhadj

Budzák

et al. 2017

Chemistry A European J

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“…Synthesis of Norlapachol (2): Compound 2 was synthesized by the Hooker oxidation methodology as an orange solid (160 mg, 0.7 mmol, 70 % yield), and characterization data are consistent with those reported in the literature , . M.p.…”

Section: Methodssupporting

confidence: 72%

“…The opportunity of generating heterocyclic compounds from naphthoquinoidal derivatives obtained from lapachones in a straightforward fashion is an additional feature to be considered (Scheme A) , . For example, our group has recently demonstrated the application of this strategy for the synthesis of fluorescent oxazoles, boron complexes mimicking BODIPYs, and a phenazine‐based 1,2,3‐triazole (Scheme B). We have shown that lipophilic oxazoles can be used for the selective cellular staining of lipid‐based structures.…”

Section: Introductionmentioning

confidence: 99%

Redox Center Modification of Lapachones towards the Synthesis of Nitrogen Heterocycles as Selective Fluorescent Mitochondrial Imaging Probes

et al. 2017

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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.

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“…The naphthoquinone ( 2 ) was synthesized by Hooker oxidation methodology and isolated as an orange solid (160 mg, 0.7 mmol, 70% yield). Characterization data are consistent with those reported in the literature (da Rocha et al, 2014 ; Dias et al, 2015 ). m.p.…”

Section: Methodssupporting

confidence: 91%

Quinone-Derived π-Extended Phenazines as New Fluorogenic Probes for Live-Cell Imaging of Lipid Droplets

et al. 2018

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We describe a new synthetic methodology for the preparation of fluorescent π-extended phenazines from the naturally-occurring naphthoquinone lapachol. These novel structures represent the first fluorogenic probes based on the phenazine scaffold for imaging of lipid droplets in live cells. Systematic characterization and analysis of the compounds in vitro and in cells led to the identification of key structural features responsible for the fluorescent behavior of quinone-derived π-extended phenazines. Furthermore, live-cell imaging experiments identified one compound (P1) as a marker for intracellular lipid droplets with minimal background and enhanced performance over the lipophilic tracker Nile Red.

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Selective endocytic trafficking in live cells with fluorescent naphthoxazoles and their boron complexes

Cited by 24 publications

References 23 publications

On the Fine‐Tuning of the Excited‐State Intramolecular Proton Transfer (ESIPT) Process in 2‐(2′‐Hydroxybenzofuran)benzazole (HBBX) Dyes

On the Fine‐Tuning of the Excited‐State Intramolecular Proton Transfer (ESIPT) Process in 2‐(2′‐Hydroxybenzofuran)benzazole (HBBX) Dyes

Redox Center Modification of Lapachones towards the Synthesis of Nitrogen Heterocycles as Selective Fluorescent Mitochondrial Imaging Probes

Quinone-Derived π-Extended Phenazines as New Fluorogenic Probes for Live-Cell Imaging of Lipid Droplets

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