1092490-83-9

Upstream product

• 1131797-24-4 2-(4-(1,3-dithian-2-yl)phenyl)-1H-phenanthro[9,10-d]imidazole 
• 623-27-8 terephthalaldehyde, 
• 84-11-7 9,10-phenanthrenequinone 
• 85-01-8 phenanthrene 

Downstream Products

• 1092490-84-0 C₂₅H₁₉N₃O₂S 
• 1092490-85-1 C₂₆H₂₁N₃O₂S 
• 1131797-24-4 2-(4-(1,3-dithian-2-yl)phenyl)-1H-phenanthro[9,10-d]imidazole 
• 1149348-07-1 4-(1H-phenanthro[9,10-d]imidazo-2-yl)benzaldehyde oxime 
• 1357573-30-8 C₃₆H₂₂Cl₂N₄ 
• 1357573-31-9 C₃₂H₂₀N₄O₂ 

Relevant academic research and scientific papers

Colorimetric and ratiometric fluorescent chemosensor for fluoride ions based on phenanthroimidazole (PI): Spectroscopic, NMR and density functional studies

The anion chemosensor based on the phenanthroimidazole conjugate of biscarbanohyrazone, probe PI was designed, synthesized and characterized. Probe PI detected fluoride ions selectively with unique absorption as well as fluorescence changes which were not observable for other halides & anions. 1H NMR and density functional studies on the system have been carried out to determine the nature of the interaction between probe PI and F- responsible for the significant fluoride-induced changes in the absorption and emission properties of probe PI. The experimental results reveal that hydrogen-bonding followed by abstraction of acidic protons of imidazole -NH and urea -NH of probe PI by the fluoride ion, leading to the formation of anionic species, is responsible for the spectral changes. Finally, the use of a test strip of the probe PI to detect fluoride was also reported.

Synthesis, spectroscopic, physicochemical properties and binding site analysis of 4-(1H-phenanthro[9,10-d]-imidazol-2-yl)-benzaldehyde fluorescent probe for imaging in cell biology: Experimental and theoretical study

In this study, the 4-(1H-phenanthro[9,10-d]-imidazol-2-yl)-benzaldehyde (PB1) was investigated as a fluorescent dye. For this reason, the spectroscopic properties in different solvents were thoroughly studied. The experimental data were supported by quantum-chemical calculations using density functional theory. Measurements and theoretical calculations showed that PB1 dye is characterized by the non-monotonic solvatochromism, strongly polar charge transfer excited state, large Stokes' shift, high fluorescence quantum yield and high fluorescence lifetime. Simulations using AutoDock presented in this study, showed that after conjugation with Concanavalin A in the active site with LYS116, the PB1 possesses the highest probability of binding affinity. The interaction between the PB1 dye and the Concanavalin A lectin has been investigated by circular dichroism spectroscopy. Conventional fluorescence microscopy imaging of Candida albicans and Yarrowia lipolytica cells, incubated with the PB1-Concanavalin A, was demonstrated. Results show that the PB1 dye is a photostable low molecular weight fluorescent probe, which emits a blue fluorescence. The results of this study have implications for designing PB1-protein conjugate as a valuable alternative to commercial probes designed for cellular labeling in biological and biomedical research. Calculated LogP value together with LogBCF show that PB1-protein conjugate is a valuable alternative to commercial probes designed for cellular labeling in biological and biomedical research.

Synthesis of 5-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzylidene)thiazolidine-2,4-dione as promising DNA and serum albumin-binding agents and evaluation of antitumor activity

A series of phenanthro[9,10-d]imidazole/oxazole and acenaphtho[1,2-d]imidazole with different aryl groups at C2-position has been synthesized. These compounds were in vitro evaluated for antitumor activity against a panel of 60 human cancer cell lines. Co

Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems

As a notorious toxin, formaldehyde (FA) poses an immense threat to human health. Aberrantly elevated FA levels lead to serious pathologies, including organ damage, neurodegeneration, and cancer. Unfortunately, current techniques limit FA imaging to general comparative studies, instead of a mechanistic exploration of its biological role, and this is presumably due to the lack of robust molecular tools for reporting FA in living systems. More importantly, despite being reductive, FA, however, can induce oxidative damage to organisms, thus providing a challenge to the mechanistic study of FA using fluorescence imaging. Herein, we presented the design and multi-application of a bright sensitive ratiometric fluorescent probe 1-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)phenyl) but-3-en-1-amine (PIPBA). With a π-extended phenylphenanthroimidazole fluorophore and an allylamine group, PIPBA exhibited high quantum yield (= 0.62) in blue fluorescent emission and selective reactivity toward FA. When sensing FA, PIPBA transformed to PIBE, which is a product capable of releasing bright green fluorescence (= 0.51) with its enhanced intramolecular charge transfer (ICT). Transformation of PIPBA to PIBE contributed to 80 nm of red shift in emission wavelength and a highly sensitive ratiometric response (92.2-fold), as well as a quite low detection limit (0.84 μM). PIPBA was successfully applied to various living systems, realizing, for the first time, ratiometric quantification (in cells), in vivo imaging (zebrafish), and living tissue imaging (vivisectional mouse under anaesthetic) of endogenous FA that was spontaneously generated by biological systems. Furthermore, with the aid of PIPBA, we obtained visual evidence for the oxidative damage of FA in both HeLa cells and renal tissue of a living mouse. The results demonstrated that FA exerted indirect oxidative damage by interacting with free radicals, thus producing more oxidizing species, which eventually caused aggravated oxidative damage to the organism. The indirect oxidative damage due to FA could be alleviated by an exogenous or endogenous antioxidant. The excellent behaviors of PIPBA demonstrate that a chemical probe can detect endogenous FA in cells/tissue/vivo, promising to be an effective tool for further exploration of the biological mechanism of FA in living systems.

A Water-Soluble Fluorescent Probe for SO2 Derivatives in Aqueous Solution and Serum Based on Phenanthroimidazole Dye

A water-soluble fluorescent SO2 derivatives probe PI-SO2 based on a phenanthroimidazole dye, and a sensitive SO2 recognition site, aldehyde was constructed. The probe PI-SO2 exhibits desirable properties such as high sensitivity, high selectivity and good water-solubility. Significantly, we have demonstrated that the probe PI-SO2 is suitable for rapidly fluorescence detecting of SO2 derivatives in aqueous solution and serum. The application of the novel probe PI-SO2 proved that it was not only a useful tool for the detection of SO2 derivatives in vitro, but also a potential assay for investigating the effects of SO2 derivatives, and demonstrating its value in practical applicationin of complex biological samples.

2-(4-Formylphenyl)phenanthroimidazole as a colorimetric and fluorometric probe for selective fluoride ion sensing

An easy-to-prepare chemosensor, 2-(4-formylphenyl) phenanthroimidazole 1, synthesized by facile onestep condensation under microwave irradiation, has been indicated to be a colorimetric and fluorometric probe for fluoride anion with good sensitivity and high selectivity. This probe shows obvious red shift and absorbance intensity changes in UV absorption and fluorescence spectra in the presence of fluoride anions. Such color and absorbance intensity changes are attributed to the deprotonation of N-H on the imidazole moiety with fluoride anion. Springer Science+Business Media, LLC 2009.

Donor-π-acceptor (D-π-A) dyad for ratiometric detection of Hg2+ and PPi

A donor-π-acceptor (D-π-A) dyad 1 has been successfully synthesized by linking phenanthrenequinone as an electron donor unit and anthraquinone as an electron acceptor unit through a phenyl ring. Dyad 1 exhibits intramolecular charge transfer and this is a key factor for the detection of Hg2+ and of the pyrophosphate ion (P2O74-, PPi) in a semi-aqueous medium. Dyad 1 exhibits absorption peaks at 430, 370, and 337 nm and an emission peak at 530 nm (λex = 430 nm). Dyad 1 exhibits a new absorption peak at 390 nm ratiometrically along with emission quenching in the presence of Hg2+ ions while the presence of PPi results in drastic ratiometric changes in the absorption and emission spectra with new peaks at 495 nm and 620 nm, respectively. The quantum yield of dyad 1 on complexation with PPi was also increased from 0.1 (free dyad) to 0.69 (dyad 1·PPi). The lowest detection limits for Hg2+ and PPi were found to be 31 nM and 46.5 nM, respectively. DFT calculations have been performed to develop a mechanism for PPi and Hg2+ ion binding with dyad 1.

A novel dual-ratiometric-response fluorescent probe for SO2/ClO? detection in cells and in vivo and its application in exploring the dichotomous role of SO2 under the ClO? induced oxidative stress

Intracellular reactive sulfur species and reactive oxygen species play vital roles in immunologic mechanism. As an emerging signal transmitter, SO2 can be generated as the anti-oxidant, while SO2 is also a potential oxidative stress-inducer in organism. Aiming to elucidate in-depth the dichotomous role of SO2 under oxidative stress, we designed a dual-response fluorescent probe that enabled the respective or successive detection of SO2 and ClO?. The probe itself emits the red fluorescence (625 nm) which can largely switch to blue (410 nm) and green fluorescence (500 nm) respectively in response to SO2 and ClO?, allowing the highly selective and accurate ratiometric quantification for both SO2 and ClO? in cells. Moreover the ultrafast (SO2: ?: within sec) and highly sensitive (detection limits: SO2: 3.5 nM; ClO?: 12.5 nM) detection were achieved. With the robust applicability, the developed probe was successfully used to quantify SO2 and endogenous ClO? in respectively the HeLa cells and the RAW 264.7 cells, as well as to visualize the dynamic of SO2/ClO? in zebrafish. The fluorescent imaging studies and flow cytometry analysis confirmed the burst-and-depletion and meanwhile the oxidative-and-antioxidative effects of intracellular SO2 under the NaClO induced oxidative stress.

A novel ratiometric fluorescent probe for “naked-eye” detection of sulfite ion: Applications in detection of biological SO3 2 ? ions in food and live cells

A new “turn-on” luminescent probe PI has been designed and synthesized for the selective detection of sulfite ions based on the mechanism of nucleophilic addition. The designed probe PI owns naked eye detection, excellent selectivity, sensitivity, rapid response (150 s) and low limits of detection (LOD) of 0.57 μM, which is an agreeable limit by the world wide expert food additive committees. Furthermore, the probe PI was used to recognize the sulfite ions level in realistic samples and live cells.

FRET-Based Probe for Monitoring pH Changes in Lipid-Dense Region of Hct116 Cells

A rhodamine conjugate (L) with a pseudo Stokes shift of 165 nm is used for probing changes in solution pH under physiological conditions. This reagent is found to be nontoxic, and the luminescence response could be used for imaging changes in endogenous pH induced by dexamethanose (DMT) in the endoplasmic reticulum.