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Recent Advances on Fluorogenic Probes Emitting in the Visible, Near-Infrared Window and Beyond: Synthesis and High-Tech Applications

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 6682

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Special Issue Editors

Dr. Atanas Kurutos

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Guest Editor

Group of Organic Synthesis and Steroechemistry, Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 9, 1113 Sofia, Bulgaria
Interests: biosensors; chemosensors; dye chemistry; fluorescent probes; theranostics

Dr. Elisabete Oliveira

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Guest Editor

BIOSCOPE Research Group, LAQV-REQUIMTE, Chemistry Department, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
Interests: bio-inspired chemosensors; luminescence; dye-doped polymers; antibiotic resistance; mesoporous silica nanoparticles; drug delivery
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Special Issue Information

Dear Colleagues,

Fluorescent probes are molecules that absorb a particular wavelength and usually emit a longer wavelength and are employed in various high-tech applications. Fluorophores are compounds that may be linked to a target molecule and used as a labeling agent for fluorescence microscopy investigation. State-of-the-art fluorescent techniques now account for the vast majority of the detection-enabling technologies used in nucleic acid recognition, molecular biology, and medicine. These fluorescent probes are an essential and quickly evolving field of research that stimulates continuing collaboration among chemists and biologists to improve the probes’ uses.

The advances in fluorescence probe development in the UV, visible, and near-infrared (NIR) region, as well as the probes' wide range of applications in bioanalytical, biological, optical imaging, and diagnostic and therapeutic applications, is the emphasis of current Special Issue. Specialists in this area are also welcomed to submit review articles.

Dr. Atanas Kurutos
Dr. Elisabete Oliveira
Guest Editors

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Keywords

biosensors
chemosensors
dye chemistry
fluorescent probes
theranostics

Published Papers (3 papers)

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Research

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14 pages, 4161 KiB

Open AccessArticle

Fluorescence Lifetimes of NIR-Emitting Molecules with Excited-State Intramolecular Proton Transfer

by Yonghao Li, Dipendra Dahal and Yi Pang

Molecules 2023, 28(1), 125; https://doi.org/10.3390/molecules28010125 - 23 Dec 2022

Cited by 5 | Viewed by 1668

Abstract

Molecular probes based on the excited-state intramolecular proton-transfer (ESIPT) mechanism have emerged to be attractive candidates for various applications. Although the steady-state fluorescence mechanisms of these ESIPT-based probes have been reported extensively, less information is available about the fluorescence lifetime characteristics of newly developed NIR-emitting dyes. In this study, four NIR-emitting ESIPT dyes with different cyanine terminal groups were investigated to evaluate their fluorescence lifetime characteristics in a polar aprotic solvent such as CH₂Cl₂. By using the time-correlated single-photon counting (TCSPC) method, these ESIPT-based dyes revealed a two-component exponential decay (τ₁ and τ₂) in about 2–4 nanoseconds (ns). These two components could be related to the excited keto tautomers. With the aid of model compounds (5 and 6) and low-temperature fluorescence spectroscopy (at −189 ℃), this study identified the intramolecular charge transfer (ICT) as one of the major factors that influenced the τ values. The results of this study also revealed that both fluorescence lifetimes and fractional contributions of each component were significantly affected by the probe structures. Full article

(This article belongs to the Special Issue Recent Advances on Fluorogenic Probes Emitting in the Visible, Near-Infrared Window and Beyond: Synthesis and High-Tech Applications)

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13 pages, 2729 KiB

Open AccessArticle

Enhanced Photodynamic Efficacy Using 1,8-Naphthalimides: Potential Application in Antibacterial Photodynamic Therapy

by Desislava Staneva, Awad I. Said, Evgenia Vasileva-Tonkova and Ivo Grabchev

Molecules 2022, 27(18), 5743; https://doi.org/10.3390/molecules27185743 - 6 Sep 2022

Cited by 6 | Viewed by 1359

Abstract

This study addresses the need for antibacterial medication that can overcome the current problems of antibiotics. It does so by suggesting two 1,8-naphthalimides (NI1 and NI2) containing a pyridinium nucleus become attached to the imide-nitrogen atom via a methylene spacer. Those fluorescent derivatives are covalently bonded to the surface of a chloroacetyl-chloride-modified cotton fabric. The iodometric method was used to study the generation of singlet oxygen (¹O₂) by irradiation of KI in the presence of monomeric 1,8-naphthalimides and the dyed textile material. Both compounds generated reactive singlet oxygen, and their activity was preserved even after they were deposited onto the cotton fabric. The antibacterial activity of NI1 and NI2 in solution and after their covalent bonding to the cotton fabric was investigated. In vitro tests were performed against the model gram-positive bacteria B. cereus and gram-negative P. aeruginosa bacteria in dark and under light iradiation. Compound NI2 showed higher antibacterial activity than compound NI1. The light irradiation enhanced the antimicrobial activity of the compounds, with a better effect achieved against B. cereus. Full article

(This article belongs to the Special Issue Recent Advances on Fluorogenic Probes Emitting in the Visible, Near-Infrared Window and Beyond: Synthesis and High-Tech Applications)

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Review

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34 pages, 8233 KiB

Open AccessReview

Photonics of Trimethine Cyanine Dyes as Probes for Biomolecules

by Pavel G. Pronkin and Alexander S. Tatikolov

Molecules 2022, 27(19), 6367; https://doi.org/10.3390/molecules27196367 - 27 Sep 2022

Cited by 12 | Viewed by 2989

Abstract

Cyanine dyes are widely used as fluorescent probes in biophysics and medical biochemistry due to their unique photophysical and photochemical properties (their photonics). This review is focused on a subclass of the most widespread and studied cyanine dyes—trimethine cyanines, which can serve as potential probes for biomolecules. The works devoted to the study of the noncovalent interaction of trimethine cyanine dyes with biomolecules and changing the properties of these dyes upon the interaction are reviewed. In addition to the spectral-fluorescent properties, elementary photochemical properties of trimethine cyanines are considered, including: photoisomerization and back isomerization of the photoisomer, generation and decay of the triplet state, and its quenching by oxygen and other quenchers. The influence of DNA and other nucleic acids, proteins, and other biomolecules on these properties is covered. The interaction of a monomer dye molecule with a biomolecule usually leads to a fluorescence growth, damping of photoisomerization (if any), and an increase in intersystem crossing to the triplet state. Sometimes aggregation of dye molecules on biomolecules is observed. Quenching of the dye triplet state in a complex with biomolecules by molecular oxygen usually occurs with a rate constant much lower than the diffusion limit with allowance for the spin-statistical factor 1/9. The practical application of trimethine cyanines in biophysics and (medical) biochemistry is also considered. In conclusion, the prospects for further studies on the cyanine dye–biomolecule system and the development of new effective dye probes (including probes of a new type) for biomolecules are discussed. Full article

(This article belongs to the Special Issue Recent Advances on Fluorogenic Probes Emitting in the Visible, Near-Infrared Window and Beyond: Synthesis and High-Tech Applications)

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