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Synthesis of Small Molecules Fluorescent Probes and Their Applications from Sensing to Imaging

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

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 10160

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Special Issue Editors

Dr. Maged Henary

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Guest Editor

Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA
Interests: organic synthesis; heterocyclic chemistry; fluorescent probes; NIR contrast agents; metal sensors; microwave synthesis; biomedical applications; bioanalytical applications
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Haiying Liu

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Guest Editor

Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI, USA
Interests: fluorescent probes; theranostics; fluorescence bioimaging
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Fluorescent probes are molecules that absorb light of a specific wavelength and emit light of a different one, typically a longer wavelength, and are used for many fields. The molecules, also known as fluorophores, can be attached to a target molecule and act as a marker for analysis with fluorescence microscopy. These fluorescent probes are an important and rapidly developing field of study that encourages continued collaboration between chemists, biologists, and clinicians to further refine the probes’ applications.

This Special Issue focuses on the progress in fluorescence probe development in the UV, visible, and NIR windows and the probes’ wide applications for various fields such as bioanalytical, biological, optical imaging, and diagnostic and therapeutic applications. Review articles by experts in the field will also be welcome.

Prof. Dr. Maged Henary
Prof. Dr. Haiying Liu
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

Synthesis of novel fluorescent probes, sensors and labels
Optical properties, reactivity, and stability of fluorescent probes
Fluorescent probes interaction with Biomolecules
Fluorescent probes as biosensors (metals, enzymatic, etc.)
Bioanalytical applications
Imaging applications

Published Papers (5 papers)

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Research

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19 pages, 1788 KiB

Open AccessArticle

Expanding Glycomic Investigations through Thiol-Derivatized Glycans

by Robert D. Hurst, Angel Nieves and Matthew Brichacek

Molecules 2023, 28(4), 1956; https://doi.org/10.3390/molecules28041956 - 18 Feb 2023

Viewed by 1692

Abstract

N-(2-thioethyl)-2-aminobenzamide (TEAB), a novel glycan auxiliary, was synthesized and its utility was evaluated. The auxiliary was conjugated to glycans by reductive amination with the water-stable reagent 2-picoline borane complex. Glycan products, which ranged from 1 to 7 linked hexoses, were all isolated in yields ranging from 60% to 90% after purification by reverse-phase chromatography. The novel conjugate introduces a convenient, shelf-stable thiol directly onto the desired free glycans with purification advantages and direct modification with efficient reactions through alkenes, halides, epoxides, disulfides, and carboxylates in yields of 49% to 93%. Subsequently, a thiol-selective modification of the BSA protein was used to generate a neoglycoprotein with a bifunctional PEG–maleimide linker. To further illustrate the utility of a thiol motif, 2-thiopyridine activation of a thiol-containing support facilitated the covalent chromatographic purification of labeled glycans in yields up to 63%. Finally, initial proof of concept of implementation in a light printed microarray was explored and validated through FITC-labeled concanavalin A binding. In conclusion, the thiol-functionalized glycans produced greatly expand the diversity of bioconjugation tools that can be developed with glycans and enable a variety of biological investigations. Full article

(This article belongs to the Special Issue Synthesis of Small Molecules Fluorescent Probes and Their Applications from Sensing to Imaging)

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11 pages, 2708 KiB

Open AccessFeature PaperArticle

Zinc Ion-Based Switch-on Fluorescence-Sensing Probes for the Detection of Tetracycline

by Yan-Cen Zhan, Jia-Jen Tsai and Yu-Chie Chen

Molecules 2022, 27(23), 8403; https://doi.org/10.3390/molecules27238403 - 01 Dec 2022

Cited by 5 | Viewed by 1362

Abstract

Tetracycline (TC) is an antibiotic that has been widely used in the animal husbandry. Thus, TC residues may be found in animal products. Developing simple and sensitive methods for rapid screening of TC in complex samples is of great importance. Herein, we demonstrate a fluorescence-sensing method using Zn²⁺ as sensing probes for the detection of TC. Although TC can emit fluorescence under the excitation of ultraviolet light, its fluorescence is weak because of dynamic intramolecular rotations, leading to the dissipation of excitation energy. With the addition of Zn²⁺ prepared in tris(hydroxymethyl)amino-methane (Tris), TC can coordinate with Zn²⁺ in the Zn²⁺-Tris conjugates to form Tris-Zn²⁺-TC complexes. Therefore, the intramolecular motions of TC are restricted to reduce nonradiative decay, resulting in the enhancement of TC fluorescence. Aggregation-induced emission effects also play a role in the enhancement of TC fluorescence. Our results show that the linear dynamic range for the detection of TC is 15–300 nM. Moreover, the limit of detection was ~7 nM. The feasibility of using the developed method for determination of the concentration of TC in a complex chicken broth sample is also demonstrated in this work. Full article

(This article belongs to the Special Issue Synthesis of Small Molecules Fluorescent Probes and Their Applications from Sensing to Imaging)

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10 pages, 4241 KiB

Open AccessArticle

A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide

by Huan Xiang, Tianqing Ye, Yanbo Li, Yanfei Lin, Dan Liu, Hongwei Zhou, Jianbo Wang and Lei Li

Molecules 2022, 27(21), 7499; https://doi.org/10.3390/molecules27217499 - 03 Nov 2022

Cited by 6 | Viewed by 1505

Abstract

Hydrogen sulfide (H₂S) as small molecular signal messenger plays key functions in numerous biological processes. The imaging detection of intracellular hydrogen sulfide is of great significance. In this work, a ratiometric fluorescent probe BH based on an asymmetric BODIPY dye for detection of H₂S was designed and synthesized. After the interaction with hydrogen sulfide, probe display colorimetric and ratiometric fluorescence response, with its maximum emission fluorescence wavelength red-shifted from 542 nm to 594 nm, which is attributed to the sequential nucleophilic reaction of H₂S leading to enhanced molecular conjugation after ring formation of the BODIPY skeleton. A special response mechanism has been fully investigated by NMR titration and MS, so that the probe has excellent detection selectivity. Furthermore, probe BH has low cytotoxicity and fluorescence imaging experiments indicate that it can be used to monitor hydrogen sulfide in living cells. Full article

(This article belongs to the Special Issue Synthesis of Small Molecules Fluorescent Probes and Their Applications from Sensing to Imaging)

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16 pages, 2398 KiB

Open AccessArticle

Effects of Cations on HPTS Fluorescence and Quantification of Free Gadolinium Ions in Solution; Assessment of Intracellular Release of Gd³⁺ from Gd-Based MRI Contrast Agents

by Angelo Scarciglia, Enza Di Gregorio, Silvio Aime and Giuseppe Ferrauto

Molecules 2022, 27(8), 2490; https://doi.org/10.3390/molecules27082490 - 12 Apr 2022

Cited by 2 | Viewed by 2193

Abstract

8-Hydroxypyrene-1,3,6-trisulfonate (HPTS) is a small, hydrophilic fluorescent molecule. Since the pKa of the hydroxyl group is close to neutrality and quickly responds to pH changes, it is widely used as a pH-reporter in cell biology for measurements of intracellular pH. HPTS fluorescence (both excitation and emission spectra) at variable pH was measured in pure water in the presence of NaCl solution or in the presence of different buffers (PBS or hepes in the presence or not of NaCl) and in a solution containing BSA. pKa values have been obtained from the sigmoidal curves. Herein, we investigated the effect of mono-, di-, and trivalent cations (Na⁺, Ca²⁺, La³⁺, Gd³⁺) on fluorescence changes and proposed its use for the quantification of trivalent cations (e.g., gadolinium ions) present in solution as acqua-ions. Starting from the linear regression, the LoD value of 6.32 µM for the Gd³⁺ detection was calculated. The effects on the emission were also analyzed in the presence of a combination of Gd³⁺ at two different concentrations and the previously indicated mono and di-valent ions. The study demonstrated the feasibility of a qualitative method to investigate the intracellular Gd³⁺ release upon the administration of Gd-based contrast agents in murine macrophages. Full article

(This article belongs to the Special Issue Synthesis of Small Molecules Fluorescent Probes and Their Applications from Sensing to Imaging)

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Review

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32 pages, 15330 KiB

Open AccessReview

H₂S Sensors: Synthesis, Optical Properties, and Selected Biomedical Applications under Visible and NIR Light

by Dongning Liu, Winston Hessler and Maged Henary

Molecules 2023, 28(3), 1295; https://doi.org/10.3390/molecules28031295 - 29 Jan 2023

Cited by 6 | Viewed by 2053

Abstract

Hydrogen sulfide (H₂S) is an essential signaling gas within the cell, and its endogenous levels are correlated with various health diseases such as Alzheimer’s disease, diabetes, Down’s syndrome, and cardiovascular disease. Because it plays such diverse biological functions, being able to detect H₂S quickly and accurately in vivo is an area of heightened scientific interest. Using probes that fluoresce in the near-infrared (NIR) region is an effective and convenient method of detecting H₂S. This approach allows for compounds of high sensitivity and selectivity to be developed while minimizing cytotoxicity. Herein, we report a review on the synthesis, mechanisms, optical properties, and selected biomedical applications of H₂S sensors. Full article

(This article belongs to the Special Issue Synthesis of Small Molecules Fluorescent Probes and Their Applications from Sensing to Imaging)

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