Cyanine dyes carrying quinoline moieties are an important class of organic molecules that are of great interest for applications in many fields like medicine, pharmacology, and engineering. Despite ...their exceptional properties, such as stability, high molar extinction coefficients, and high pH‐sensitivity, this class of dyes has been less analyzed and reviewed in the last few decades. Therefore, this review article focuses on discussing the history of quinoline compounds, various synthetic routes to prepare quinolinium salts and symmetrical and asymmetrical mono‐, di‐, tri‐, penta‐ and heptamethine cyanine dyes, containing quinoline moieties, together with their optical properties and applications as photosensitizers in photodynamic therapy, probes in biomolecules for labeling of nucleic acids, as well as imaging agents.
Cyanine dyes: This review article discusses the history of quinoline compounds, synthetic routes to prepare quinolinium salts and symmetrical and asymmetrical mono‐, di‐, tri‐, penta‐, and heptamethine cyanine dyes, containing quinoline moieties, their optical properties and applications as photosensitizers in photodynamic therapy, probes in biomolecules labeling of nucleic acids, and imaging agents.
The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising ...functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated improvements in cell permeability, solubility, and other pharmacologic properties. For these and other numerous reasons, fluorination of molecules has grown in popularity in various fields of chemistry. Many reports show the effects observed from increasing the number of fluorine atoms on a fluorophore scaffold. This report will cover the most significant applications and improvements that fluorine has contributed to in various dye scaffolds such as BODIPY, rhodamine, phthalocyanine, and cyanine in the recent decade.
Viruses have been a long-term source of infectious diseases that can lead to large-scale infections and massive deaths. Especially with the recent highly contagious coronavirus (COVID-19), antiviral ...drugs were developed nonstop to deal with the emergence of new viruses and subject to drug resistance. Nitrogen-containing heterocycles have compatible structures and properties with exceptional biological activity for the drug design of antiviral agents. They provided a broad spectrum of interference against viral infection at various stages, from blocking early viral entry to disrupting the viral genome replication process by targeting different enzymes and proteins of viruses. This review focused on the synthesis and application of antiviral agents derived from various nitrogen-containing heterocycles, such as indole, pyrrole, pyrimidine, pyrazole, and quinoline, within the last ten years. The synthesized scaffolds target HIV, HCV/HBV, VZV/HSV, SARS-CoV, COVID-19, and influenza viruses.
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.
The signal-to-background ratio (SBR) is the key determinant of sensitivity, detectability and linearity in optical imaging. As signal strength is often constrained by fundamental limits, background ...reduction becomes an important approach for improving the SBR. We recently reported that a zwitterionic near-infrared (NIR) fluorophore, ZW800-1, exhibits low background. Here we show that this fluorophore provides a much-improved SBR when targeted to cancer cells or proteins by conjugation with a cyclic RGD peptide, fibrinogen or antibodies. ZW800-1 outperforms the commercially available NIR fluorophores IRDye800-CW and Cy5.5 in vitro for immunocytometry, histopathology and immunoblotting and in vivo for image-guided surgery. In tumor model systems, a tumor-to-background ratio of 17.2 is achieved at 4 h after injection of ZW800-1 conjugated to cRGD compared to ratios of 5.1 with IRDye800-CW and 2.7 with Cy5.5. Our results suggest that introducing zwitterionic properties into targeted fluorophores may be a general strategy for improving the SBR in diagnostic and therapeutic applications.
Celotno besedilo
Dostopno za:
DOBA, IJS, IZUM, KILJ, NUK, PILJ, PNG, SAZU, SIK, UILJ, UKNU, UL, UM, UPUK
Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored ...for particular applications. Generally, modifications at the
-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and S
1 nucleophilic substitution of the chlorine atom at the
-position of the dye. Herein, a series of 15
phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.
Pyrazoles are highly essential heterocyclic structures prevalent in biologically active products used widely throughout various disciplines of chemical industry‐including medicine and agriculture. ...The efficacy of these pyrazole species is enhanced through the introduction of fluorine and corresponding functionalities; therefore, synthetic methods for the fluorination of these structures is highly appealing which follows the overall trend of increasing interest in fluorination chemistry. Toward assimilating the known techniques for fluorine incorporation to the pyrazole heterocyclic structure we have reviewed both the new and traditional synthetic approaches to the assembly of functionalized pyrazole derivatives. Specifically, efficient synthetic methods and regioselective incorporation of fluorine and fluorine containing functional groups into different pyrazole ring systems are examined.
Methods for the assembly of fluorinated pyrazoles and the selective incorporation of fluorine and fluorine‐containing moieties into the pyrazolic architecture are reviewed. Nucleophilic, electrophilic, radical and metal‐mediated fluorination processes are considered. Reagents, precursors and reaction conditions found most suitable in processes leading to fluorinated pyrazoles are examined in detail.
Carbocyanine dyes are a unique class of organic molecules with high molar extinction coefficients and characteristically long absorption bands with absorption maxima ranging from 500 to 1000 nm ...making them extremely useful in numerous applications ranging from photography to medicine. Using various synthetic procedures, the conjugated system of these compounds can be modified to yield specific absorption and fluorescence spectra. One way to alter these conjugated systems is to include two different heterocycles thereby producing unsymmetrical dyes. The attractiveness of unsymmetrical carbocyanines has increased significantly over the last decade. For monomethine carbocyanines, there are many methods to synthesize unsymmetrical dyes, but for tri-, penta- and heptamethines the synthesis is more complicated. The synthesis of unsymmetrical carbocyanine dyes is excellent for modifying a dyes absorption wavelength, preparing it for conjugation, or altering the dyes polarity or solubility. The few known unsymmetrical carbocyanine dyes have found use in DNA labeling, dye-sensitized solar cells, and many other applications. There is a great lack of unsymmetrical carbocyanines in the literature and no collective review of them therefore we have put together this review detailing their synthesis and applications.
•Carbocyanine dyes are an immense class of compounds with extensive applications.•Synthetic methods of unsymmetrical carbocyanine dyes.•Microwave and solid-phase conditions can be used for unsymmetrical dye synthesis.•Absorption and fluorescence wavelengths can be modified using unsymmetrical dyes.•Unsymmetrical dyes can alter polarity and solubility causing less aggregation.
To address two fundamental and unsolved problems in optical imaging (nonspecific uptake of near‐infrared fluorophores by normal tissues and organs and incomplete elimination of unbound targeted ...fluorophores from the body), novel zwitterionic near‐infrared fluorophores (e.g., ZW800‐1) were synthesized and their performance compared in vivo to conventional molecules (e.g., ICG) as a function of charge, charge distribution, and hydrophobicity (see picture).
Squaraine dye is a popular class of contrast near-infrared (NIR) dyes. Squaraine dyes have shown the ability to be modified with various heterocycles. The indole moiety is the most notable ...heterocycle incorporated in squaraine dyes. A tremendous amount of work has gone into developing indole-based squaraine dyes and determining their applications. The optical properties of squaraine dyes containing an indole moiety facilitate high quantum yields and molar absorptivity, but the absorbance maxima is capped near 700 nm. This is the major limitation of indole-based squaraine dyes. In comparison, other heterocycles with larger conjugated systems such as quinoline and perimidine have demonstrated promising optical properties and immense potential for modifications, albeit with limited development. Quinoline- and perimidine-based squaraine dyes have molar extinction coefficients over 100,000 M
cm
and absorbances over 800 nm. This report will look at indole-, quinoline-, and perimidine-based squaraine dyes. Due to the sheer number of reported dyes, the search for indole-based squaraine dyes has been limited to reports from the past five years (2018-2023). For quinoline- and perimidine-based squaraine dyes, a holistic search was performed to analyze the optical properties and applications, due to the abovementioned limitation. This report will evaluate the three different classes of squaraines: indole-, quinoline-, and perimidine-based, to evaluate their optical properties and applications, with the goal of encouraging the exploration of other heterocycles for use in squaraine dyes.
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