Aggregation induced emission in 1,8-naphthalimide embedded nanomicellar architecture as a platform for fluorescent ratiometric pH-probe with biomedical applications

Georgiev, Nikolai I.; Bryaskova, Rayna; Ismail, Selen R.; Philipova, Nikoleta D.; Uzunova, Veselina; Bakov, Ventsislav V.; Tzoneva, Rumiana; Bojinov, Vladimir B.

doi:10.1016/j.jphotochem.2021.113380

Cited by 15 publications

(5 citation statements)

References 98 publications

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“…To analyze the cytotoxic effect of PAA 40 -b-PnBA 95 micelles loaded with the drug, an MTT test (Invitrogen, Carlsbad, CA, USA) was performed as previously described [ 34 ], with some modifications. The adherent cells were treated with a solution of PAA 40 -b-PnBA 95 micelles + loaded drug at a concentration of 0.25 mg/mL and with a solution of PAA 40 -b-PnBA 95 micelles at the same concentration (0.25 mg/mL).…”

Section: Methodsmentioning

confidence: 99%

Novel Fluorescent Benzimidazole-Hydrazone-Loaded Micellar Carriers for Controlled Release: Impact on Cell Toxicity, Nuclear and Microtubule Alterations in Breast Cancer Cells

et al. 2023

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Fluorescent micellar carriers with controlled release of a novel anticancer drug were developed to enable intracellular imaging and cancer treatment simultaneously. The nanosized fluorescent micellar systems were embedded with a novel anticancer drug via the self-assembling behavior of well-defined block copolymers based on amphiphilic poly(acrylic acid)-block-poly(n-butyl acrylate) (PAA-b-PnBA) copolymer obtained by Atom Transfer Radical Polymerization (ATRP) and hydrophobic anticancer benzimidazole-hydrazone drug (BzH). Through this method, well-defined nanosized fluorescent micelles were obtained consisting of a hydrophilic PAA shell and a hydrophobic PnBA core embedded with the BzH drug due to the hydrophobic interactions, thus reaching very high encapsulation efficiency. The size, morphology, and fluorescent properties of blank and drug-loaded micelles were investigated using dynamic light scattering (DLS), transmission electron microscopy (TEM), and fluorescent spectroscopy, respectively. Additionally, after 72 h of incubation, drug-loaded micelles released 3.25 μM of BzH, which was spectrophotometrically determined. The BzH drug-loaded micelles were found to exhibit enhanced antiproliferative and cytotoxic effects on MDA-MB-231 cells, with long-lasting effects on microtubule organization, with apoptotic alterations and preferential localization in the perinuclear space of cancer cells. In contrast, the antitumor effect of BzH alone or incorporated in micelles on non-cancerous cells MCF-10A was relatively weak.

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Section: Methodsmentioning

confidence: 99%

Novel Fluorescent Benzimidazole-Hydrazone-Loaded Micellar Carriers for Controlled Release: Impact on Cell Toxicity, Nuclear and Microtubule Alterations in Breast Cancer Cells

et al. 2023

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“…Recently, we reported a water-soluble nanosized probe as an interesting AIE strategy for intracellular imaging [ 146 ]. This probe was obtained after the incorporation of aggregated 1,8-naphthalimide molecules ( 48 ) in poly(acrylic acid)- block -poly( n -butyl acrylate) micelles.…”

Section: Fluorescent Probes Based On Aggregation-induced Emission (Aie)mentioning

confidence: 99%

Fluorescent Probes as a Tool in Diagnostic and Drug Delivery Systems

et al. 2023

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Over the last few years, the development of fluorescent probes has received considerable attention. Fluorescence signaling allows noninvasive and harmless real-time imaging with great spectral resolution in living objects, which is extremely useful for modern biomedical applications. This review presents the basic photophysical principles and strategies for the rational design of fluorescent probes as visualization agents in medical diagnosis and drug delivery systems. Common photophysical phenomena, such as Intramolecular Charge Transfer (ICT), Twisted Intramolecular Charge Transfer (TICT), Photoinduced Electron Transfer (PET), Excited-State Intramolecular Proton Transfer (ESIPT), Fluorescent Resonance Energy Transfer (FRET), and Aggregation-Induced Emission (AIE), are described as platforms for fluorescence sensing and imaging in vivo and in vitro. The presented examples are focused on the visualization of pH, biologically important cations and anions, reactive oxygen species (ROS), viscosity, biomolecules, and enzymes that find application for diagnostic purposes. The general strategies regarding fluorescence probes as molecular logic devices and fluorescence–drug conjugates for theranostic and drug delivery systems are discussed. This work could be of help for researchers working in the field of fluorescence sensing compounds, molecular logic gates, and drug delivery.

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“…Due to portability, very low cost, and easier operation, paper is a useful material for the fabrication of chemosensing devices [87][88][89][90][91]. That is why the extension of the principles of molecular sensors from liquid solution onto solid support could open up new directions for practical applications [92][93][94][95]. Motivated by this principle, in order to obtain strip papers with chemosensing properties based on 5, a methanolic solution of 5 was poured onto a filter paper, and the solvent was evaporated.…”

Section: () Log ()mentioning

confidence: 99%

Design and Synthesis of a Novel ICT Bichromophoric pH Sensing System Based on 1,8-Naphthalimide Fluorophores as a Two-Input Logic Gate and Its Antibacterial Evaluation

2023

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The synthesis, sensor activity, and logic behavior of a novel 4-iminoamido-1,8-naphthalimide bichromophoric system based on a “fluorophore-receptor” architecture with ICT chemosensing properties is reported. The synthesized compound showed good colorimetric and fluorescence signaling properties as a function of pH and proved itself as a promising probe for the rapid detection of pH in an aqueous solution and base vapors in a solid state. The novel dyad is able to work as a two-input logic gate with chemical inputs H+ (Input 1) and HO− (Input 2) executing INHIBIT logic gate. The synthesized bichromophoric system and the corresponding intermediates demonstrated good antibacterial activity toward Gram (+) and Gram (−) bacteria when compared with the Gentamycin standard.

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Aggregation induced emission in 1,8-naphthalimide embedded nanomicellar architecture as a platform for fluorescent ratiometric pH-probe with biomedical applications

Cited by 15 publications

References 98 publications

Novel Fluorescent Benzimidazole-Hydrazone-Loaded Micellar Carriers for Controlled Release: Impact on Cell Toxicity, Nuclear and Microtubule Alterations in Breast Cancer Cells

Novel Fluorescent Benzimidazole-Hydrazone-Loaded Micellar Carriers for Controlled Release: Impact on Cell Toxicity, Nuclear and Microtubule Alterations in Breast Cancer Cells

Fluorescent Probes as a Tool in Diagnostic and Drug Delivery Systems

Design and Synthesis of a Novel ICT Bichromophoric pH Sensing System Based on 1,8-Naphthalimide Fluorophores as a Two-Input Logic Gate and Its Antibacterial Evaluation

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