Applications of Fluorescent Sensor Based on 1H-pyrazolo[3,4-b]quinoline in Analytical Chemistry

Abstract

Fluorescent dye 2-[(2-Hydroxyethyl)-(1,3-diphenyl-1H-pyrazolo[3,4-b]quinolin-6-ylmethyl)-amino]ethanol (LL1) was examined for its efficiency in the detection of small inorganic cations (lithium, sodium, barium, calcium, magnesium, cadmium, lead and zinc). The dye was synthesized in the laboratory and investigated by means of both, steady-state and time-resolved fluorescence techniques. This compound acts as a fluorescent sensor suitable for detection of small inorganic cations (lithium, sodium, barium, calcium, magnesium, cadmium, lead and zinc) in strongly polar solvent (acetonitrile). An electron transfer from the electro-donative part (receptor) of the molecule to the acceptor part (fluorophore) is thought to be the main mechanism that underlies functionality of the compound as a sensor. This process can be retarded upon complexation of the receptor moiety by inorganic cations. Relatively high sensitivity but poor selectivity of the aminoalcohol thatcontains indicator towards the two-valued cations was observed. However, upon addition of some amounts of water the selectivity of this sensor has been enhanced (especially towards lead cation). The preliminary results in analytical application of the sensor are discussed.

A novel fluorescent probe with a pyrazolo[4,3-c]quinoline core selectively recognizes c-MYC promoter G-quadruplexes

“…5 and Table S4, ESI †). The torsion angles (Table S5, ESI †) of C(17), C (18), C(20), N(2) and N(3) are zero, which prove the presence of these atoms in one ring system. 11) are very small.…”

“…Generally, an ideal G-quadruplex fluorescent probe is assumed to consist of a fluorescent signaling unit specifically recognizing the G-quadruplex structure. Pyrazoloquinolines have been shown to be efficient organic emitters, [16][17][18] with applications in fluorescence sensing 19,20 and electroluminescence. 21 Recently, a derivative of this class of compounds showed a selective binding to human telomeric G4 multimers over monomeric ones.…”

1H-Pyrazolo[3,4-b]quinolines: Synthesis and Properties over 100 Years of Research

“…It was found that this compound can act as a highly efficient Since the aforementioned studies on pyrazoloquinoline-based sensors were reported, almost a decade passed until this stem was followed. Then, between 2010 and 2013, Mac and co-workers published a series of articles on ion-sensitive pyrazoloquinolines, which varied by the molecular architecture of the receptor unit (see Figure 16b) [175][176][177]. All of the sensors presented (PQ 1a-d) were designed for PET signalling, and they maintained the connection between the receptor unit and the pyrazoloquinoline chromophore via the non-conjugated methylene spacer.…”

Electrocatalytic Multicomponent Transformation of Aldehyde, 5‐Amino‐3‐methyl‐1‐phenylpyrazole and Dimedone: An Efficient Protocol for Substituted Pyrazolo[3,4‐b]quinolines

“…As a class of important quinoline derivatives, pyrazolo [3,4-b]quinoline derivatives have potential antiviral, [5] antimalarial, [6] and serum cholesterol lowering activities, [7] and blue luminescence properties. [8] In consideration of the above potential application prospects of pyrazolo [3,4-b]quinoline derivatives, their synthesis is always a research hotspot in organic synthetic chemistry. In the reported literatures, the most common synthesis method is the condensation of aldehydes with 1,3-dicarbonyl compounds and aminopyrazole in organic solvents.…”

“…Research shows that they exhibited potential antiviral, [2] antimalarial, [3] and anti‐inflammatory [4] properties. As a class of important quinoline derivatives, pyrazolo[3,4‐b]quinoline derivatives have potential antiviral, [5] antimalarial, [6] and serum cholesterol lowering activities, [7] and blue luminescence properties [8] . In consideration of the above potential application prospects of pyrazolo[3,4‐ b ]quinoline derivatives, their synthesis is always a research hotspot in organic synthetic chemistry.…”