Proton transfer in fluorescent secondary amines: synthesis, photophysics, theoretical calculation and preparation of photoactive phosphatidylcholine-based liposomes

Kroetz, Thais; Santos, Marinalva Cardoso dos; Beal, Roiney; Zanotto, Gabriel Modernell; Santos, Fabiano S.; Giacomelli, Fernando C.; Gonçalves, Paulo Fernando Bruno; Lima, Vânia Rodrigues de; Dal-Bó, Alexandre Gonçalves; Rodembusch, Fabiano Severo

doi:10.1039/c9pp00017h

Cited by 13 publications

(7 citation statements)

References 74 publications

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“…The calculated molar absorptivity values (ε, ∼10 4 M −1 ⋅cm −1 ), as well as the radiative rate constants (ke 0 , ∼10 8 s −1 ) indicate spin and symmetry-allowed electronic transitions, which could be related to 1 π-π* transitions. Similar values were obtained for the same compounds in organic media, as discussed in the literature [41]. Moreover, an almost constant radiative lifetime τ0 indicates that these benzazoles seem to populate the same excited state after radiation absorption.…”

Section: Synthesis and Photophysical Characterizationsupporting

confidence: 87%

“…In addition, for compounds 13-14 and 16-17, broad ab- The photophysical investigation was carried out in PBS (pH 7.2) at a concentration of 10 −5 M. The characterization data from the electronic ground and excited state are summarized in Table 1. As shown in Figure 1, the benzazoles exhibit absorption maxima in the UV region, as already observed in organic media [41]. The benzothiazoles produced red-shifted absorption maxima compared to their benzoxazole analogs, which can be explained by the better electron delocalization transferred from the sulfur to the oxygen [12].…”

Section: Synthesis and Photophysical Characterizationsupporting

confidence: 66%

“…The fluorescent secondary amines used in this study are similar to those reported previously [41]. Generally, the reaction of the formyl derivatives 1-2 [14] with an equimolar quantity of amines 3-5 in dry isopropanol/acetic acid (catalyst) under reflux yielded the respective imines 6-11 (Scheme 1).…”

Section: Synthesis and Photophysical Characterizationsupporting

confidence: 62%

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Interaction Study between ESIPT Fluorescent Lipophile-Based Benzazoles and BSA

et al. 2021

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In this study, the interactions of ESIPT fluorescent lipophile-based benzazoles with bovine serum albumin (BSA) were studied and their binding affinity was evaluated. In phosphate-buffered saline (PBS) solution these compounds produce absorption maxima in the UV region and a main fluorescence emission with a large Stokes shift in the blue–green regions due to a proton transfer process in the excited state. The interactions of the benzazoles with BSA were studied using UV-Vis absorption and steady-state fluorescence spectroscopy. The observed spectral quenching of BSA indicates that these compounds could bind to BSA through a strong binding affinity afforded by a static quenching mechanism (Kq~1012 L·mol−1·s−1). The docking simulations indicate that compounds 13 and 16 bind closely to Trp134 in domain I, adopting similar binding poses and interactions. On the other hand, compounds 12, 14, 15, and 17 were bound between domains I and III and did not directly interact with Trp134.

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Section: Synthesis and Photophysical Characterizationsupporting

confidence: 87%

Section: Synthesis and Photophysical Characterizationsupporting

confidence: 66%

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Interaction Study between ESIPT Fluorescent Lipophile-Based Benzazoles and BSA

et al. 2021

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“…The three synthesized dyes were also subjected to the sodium dodecyl sulfate (SDS) test ,,, to verify their emissive properties in lipophilic media (Figure ). Thus, the three dyes were tested below and above the critical micellar concentration (cmc, 8 mM) to have their emission intensities in lipophilic milieus verified.…”

Section: Resultsmentioning

confidence: 99%

Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes

Sodre

Guido

Souza³

et al. 2020

J. Org. Chem.

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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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“…Characterization of the physico-chemical properties of membranes also provides important insights into the design and development of new lipid-based nanodevices that can be used in the diagnosis and therapy of diseases. 6,11…”

Section: Introductionmentioning

confidence: 99%