Green fluorescence pyrene-based dye as a new π-extended system: Synthesis, photophysical and theoretical studies

França, Bruna M. de; Forero, Josué S. Bello; Garden, Simon J.; Ribeiro, Emerson Schwingel; Souza, Rodrigo da Silva; Teixeira, Raquel Souza; Correa, Rodrigo

doi:10.1016/j.dyepig.2017.09.003

Cited by 20 publications

(8 citation statements)

References 27 publications

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“…2). In fact, in a previous paper, we reported the excimer formation of TPPy in high concentrations (10 −4 mol L −1 in THF) as a broad shoulder at 530 nm in conjunction with the monomer fluorescence at 490 nm (28). As can be seen in Fig.…”

Section: Discussionmentioning

confidence: 88%

“…PBA (1‐pyrenebutyric acid) is the precursor reagent of the TPPy molecule (4‐(3,6,8‐tris(phenylethynyl)pyren‐1‐yl) butanoic acid), synthesized by our group in order to shift the maximum absorption peak to the visible region of the electromagnetic spectrum. The maximum absorption peaks of PBA in the UV region (278 and 346 nm, in DMSO) make it difficult to use in PDT (28). After the structural modification of the molecule, the TPPy was obtained and a redshift of the maximum absorption peaks to the visible region spectrum (335 and 451 nm, in DMSO) was observed, thus favoring the use of visible light for PDT tests.…”

Section: Discussionmentioning

confidence: 99%

“…4‐(3,6,8‐tris(phenylethynyl)pyren‐1‐yl)butanoic acid (TPPy) (C 44 H 28 O 2 , M.W: 588.69; ~95%) was previously synthesized by our research group (28). 1‐pyrenebutyric acid (C 20 H 16 O 2 , M.W: 288.34; ~97%) phosphate‐buffered saline tablet and Triton™ X‐100 were purchased from Sigma‐Aldrich ® .…”

Section: Methodsmentioning

confidence: 99%

“…So, in this work, we show a recently synthesized green fluorescent pyrene‐based photosensitizer, the TPPy (Fig. 1) (28), which encompasses all the above‐mentioned characteristics. For evaluating the application of the TPPy in PDT, we studied the antitumor photoactivity by using the murine melanoma cell line (B16F10) as a model for in vitro PDT.…”

Section: Introductionmentioning

confidence: 95%

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In vitro Studies of Antitumor Effect, Toxicity/Cytotoxicity and Skin Permeation/Retention of a Green Fluorescence Pyrene‐based Dye for PDT Application

França

Ghasemishahrestani

Souza

et al. 2020

Photochem & Photobiology

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Photosensitizers (PS) are compounds that can generate reactive oxygen species under irradiation of appropriate light and are widely used in photodynamic therapy (PDT). Currently, topical PDT is an effective treatment for several skin diseases, including bacterial infections, fungal mycoses and psoriasis. In addition, PDT is also used to treat nonmelanoma skin cancer and can be a potential tool for melanoma, associated with other treatments. In this work, we evaluated the antitumor photoactivity of a new pyrene‐based PS (TPPy) by using the murine melanoma cell line (B16F10). The in vitro permeation/retention tests in porcine ear skin were also performed in order to evaluate the potential application of the PS for topical use in skin cancer. Moreover, to determine the toxicity in vivo, we used the Galleria mellonella as an alternative animal model of study. The results showed that TPPy is a promising PS for application in PDT, with potential antitumor photoactivity (IC50 6.5 μmol L‐1), absence of toxicity in the G. mellonella model at higher concentration (70.0 mmol L−1) and the accumulation tendency in the epidermis plus dermis sites (165.20 ± 4.12 ng cm−2).

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Section: Discussionmentioning

confidence: 88%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 95%

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In vitro Studies of Antitumor Effect, Toxicity/Cytotoxicity and Skin Permeation/Retention of a Green Fluorescence Pyrene‐based Dye for PDT Application

França

Ghasemishahrestani

Souza

et al. 2020

Photochem & Photobiology

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“…of donor (acceptor) the linker molecule was replaced by a methyl group, and TD-DFT was employed using long range corrected CAM-B3LYP functional, which is known to provide correct (experimental) excitation energies for aromatic hydrocarbon derivatives (de França et al, 2018).…”

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confidence: 99%

Anharmonic Molecular Motion Drives Resonance Energy Transfer in peri-Arylene Dyads

et al. 2020

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Spectral and dynamical properties of molecular donor-acceptor systems strongly depend on the steric arrangement of the constituents with exciton coupling J as a key control parameter. In the present work we study two peri-arylene based dyads with orthogonal and parallel transition dipoles for donor and acceptor moieties, respectively. We show that the anharmonic multi-well character of the orthogonal dyad's intramolecular potential explains findings from both stationary and time-resolved absorption experiments. While for a parallel dyad, standard quantum chemical estimates of J at 0 K are in good agreement with experimental observations, J becomes vanishingly small for the orthogonal dyad, in contrast to its ultrafast experimental transfer times. This discrepancy is not resolved even by accounting for harmonic fluctuations along normal coordinates. We resolve this problem by supplementing quantum chemical approaches with dynamical sampling of fluctuating geometries. In contrast to the moderate Gaussian fluctuations of J for the parallel dyad, fluctuations for the orthogonal dyad are found to follow non-Gaussian statistics leading to significantly higher effective J in good agreement with experimental observations. In effort to apply a unified framework for treating the dynamics of optical coherence and excitonic populations of both dyads, we employ a vibronic approach treating electronic and selected vibrational degrees on an equal footing. This vibronic model is used to model absorption and fluorescence spectra as well as donor-acceptor transport dynamics and covers the more traditional categories of Förster and Redfield transport as limiting cases.

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Studying Local Electrostatics by Terahertz Spectroscopy Using Amines as a Probe

Schulke,

Nolten,

Schwaab

et al. 2023

ChemPhysChem

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In a previous study[1] we could show that a large amplitude mode of the zwitterion glycine can serve as a sensitive probe for protonation and allows to deduce local pKa values. Here we show that the underlying concept is more general:We present the results of a pH dependend measurement of Terahertz‐FTIR (THz‐FTIR) spectra of solvated amines, i.e. Diethylamine (DEA), Triethylamine (TEA), and Diisopropylamine (DiPA). We show that amines serve as a sensitive, label free probe for local protonation. Protonation of the amines yield intensity changes which can be quantified by precise THz spectroscopy (30 cm−1 ‐ 450 cm−1). A detailed analysis allows us to correlate the titration spectra of solvated amines in the THz range with pKa values. This demonstrates the potential of THz spectroscopy to probe the charge state of biomolecules in water in a label free manner.

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Green fluorescence pyrene-based dye as a new π-extended system: Synthesis, photophysical and theoretical studies

Cited by 20 publications

References 27 publications

In vitro Studies of Antitumor Effect, Toxicity/Cytotoxicity and Skin Permeation/Retention of a Green Fluorescence Pyrene‐based Dye for PDT Application

In vitro Studies of Antitumor Effect, Toxicity/Cytotoxicity and Skin Permeation/Retention of a Green Fluorescence Pyrene‐based Dye for PDT Application

Anharmonic Molecular Motion Drives Resonance Energy Transfer in peri-Arylene Dyads

Studying Local Electrostatics by Terahertz Spectroscopy Using Amines as a Probe

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