Reactions of Phenanthraquinone and Retenequinone with Aldehydes and Ammonium Acetate in Acetic Acid Solution<sup>1</sup>

Steck, Edgar A.; Day, Allan R.

doi:10.1021/ja01243a043

Cited by 296 publications

(145 citation statements)

References 0 publications

Supporting

Mentioning

143

Contrasting

Order By: Relevance

“…5,6 cis-[Ru(bpy)2Cl2]·2H2O was prepared according to a literature method, 7 and was then synthesized with the corresponding ligand PIP(V), and the complex Ru(bpy)2PIP(V) was obtained.…”

Section: Methodsmentioning

confidence: 99%

Fluorometric Determination of DNA Using a New Ruthenium Complex Ru(bpy)2PIP(V) as a Nucleic Acid Probe

Song

Liu

et al. 2002

ANAL. SCI.

View full text Add to dashboard Cite

A nucleic acid fluorescence probe is used to label nucleic acid, which is convenient, fast, and highly sensible, and has thus become more widely used in resent years. [1][2][3] Because a metal complex can be used as a DNA probe in structure and conformation, the binding of a metal complex to DNA has been the subject of intense investigations. 4 Because the special photoelectric characteristics of ruthenium have attracted high attention, we synthesized a new ligand, 2-phenyl(5-fluoro)-imidazo[ f ]-1,10-phenanthroline (PIP(V)), and its complex, Ru(bpy)2PIP(V). The fluorescence spectrum of the interaction between the complex and DNA was studied. A very strong fluorescence peak can be obtained at a wavelength of 589 nm (λex = 471 nm) with the addition of DNA; also, the fluorescence intensity is in proportion to the concentrations of DNA. A fluorescence method was used to determine DNA. The linear range was 0 -25 µg/mL, and the limit of detection was 4.8 µg/mL. The condition of experiment was optimized and the interference of the coexisting substance was studied. This method is simple, convenient and fast, which has the advantage of a high determination sensitivity in synthesized samples. ExperimentalReagent Double-distilled water was used to prepare all solutions. 1,10-Phenanthroline was of analytical reagent grade. When the interaction between a complex and DNA was studied, the concentration of the complex (Ru(bpy)2PIP(V)) was 1 × 10 -4 mol/L. Tris(trihydroxymethylaminomethane)hydrochloride (pH 7.4) was used as a buffer solution, and its concentration was 0.2 mol/L. The concentration of calf thymus DNA (biochemical agent) was 100 µg/mL. ApparatusThe fluorescence intensity was measured with an RF-540 spectrofluorometer (Japan) with a quartz cell (1 cm × 1 cm crosssection) equipped with a xenon lamp and dual monochromator.Ultraviolet-visible absorption spectra were recorded on a Perkin-Elmer lambda 17 spectrophotometer (USA) using 1 cm path-length cells. The pH was measured with a Model PHB4pH meter (Shanghai Leici Equipment Factory, China). MethodsThe synthesis of PIP(V) was carried out according to a reported procedure. 5,6 cis-[Ru(bpy)2Cl2]·2H2O was prepared according to a literature method, 7 and was then synthesized with the corresponding ligand PIP(V), and the complex Ru(bpy)2PIP(V) was obtained.After a 0.5 ml Ru(bpy)2PIP(V) solution (1 × 10 -4 mol/L) and a 1.0 mL Tris buffer solution (0.5 mol/L) were added to a 10 mL comparison tube, a DNA solution was added. The mixture was diluted to the scale, shaken and left standing for 5 min. The fluorescence intensity was measured with the following settings of the spectrofluorometer: excitation wavelength (λex), 471 nm; emission wavelength (λem), 589 nm. Blank was also measured. Results and DiscussionThe excitation and emission spectraThe excitation and emission spectra for the determination of the complex and DNA are depicted in Fig. 1, according to determination method. Although the fluorescence peak of the blank was weak at 589 nm (λex = 471 nm), a very strong fluor...

show abstract

“…5,6 cis-[Ru(bpy)2Cl2]·2H2O was prepared according to a literature method, 7 and was then synthesized with the corresponding ligand PIP(V), and the complex Ru(bpy)2PIP(V) was obtained.…”

Section: Methodsmentioning

confidence: 99%

Fluorometric Determination of DNA Using a New Ruthenium Complex Ru(bpy)2PIP(V) as a Nucleic Acid Probe

Song

Liu

et al. 2002

ANAL. SCI.

View full text Add to dashboard Cite

show abstract

“…Phenanthroimidazole based systems due to the dramatic supramolecular properties, stability, ease of synthesis, a high extinction coefficient and tuneable photophysical properties have been explored as potential chromophores in a molecular-tweezers system for explosives [45], amine sensors [46,47], fluorophore in a super-radiant laser dye [48], fluorescent tag [49], OLED materials [50 -52] and chemosensors [53 -56]. The one-step synthesis of phenanthroimidazole derivatives has remarkably increased our own interest to involve a variety of aldehydes that may further extend the way for the introduction of other functionalities and to extend the conjugation for different purposes.…”

Section: Design and Synthesis Of Target Moleculesmentioning

confidence: 99%

“…Phenanthrene was first oxidized [67] by K 2 Cr 2 O 7 in aqueous-acidic medium to obtain 9,10-phenanthroquinone 2 in good yield (76%). Compound 2 upon reaction [45] with different aromatic aldehydes in the presence of ammonium acetate (AcONH 4 ) gave derivatives 3a-f in 65%-80% yields. It is important to mention that 2 upon reaction with teraphthaldehyde gives mixture of products that were separated through column chromatography to obtain compound 3f as a major product (~85%) and bisphenanthroimidazolyl derivative 4 as a minor by product.…”

Section: Design and Synthesis Of Target Moleculesmentioning

confidence: 99%

Design and Synthesis of Some Imidazolyl Derivatives: Photophysical Studies and Application in the Detection of Anions

Shahid¹,

Ali²,

Razi³

et al. 2016

CHEM

View full text Add to dashboard Cite

Abstract:A fluorescent probe based on dicyanovinylphenanthroimidazole (DCPPI) has been designed and synthesized and its potential application to recognize F -and CN -ions via different channels have been tested in different mediums. DCPPI shows intramolecular charge transfer process and exhibit ratiometric response toward F -and CN -ions. The change in physicochemical properties of DCPPI in the presence of cyanide can be attributed to the formation of Michael type adduct, DCPPIA whereas both F -and CN -ions have shown affinities to interact with NH fragment of imidazolyl unit under the condition. The possible mode of interaction has been confirmed by absorption, emission, NMR and ESI-MS spectral data analysis.

show abstract

“…1,10-Phenanthroline-5,6-dione, [20] 4HEPIP, [21] and [Ru(L) 4 Cl 2 ] [22] were synthesised according to literature procedures. The synthetic route for ligand 4HEPIP and complexes 1 and 2 are given in Fig.…”

Section: Synthesis and Characterisation Of Ligand And Complexesmentioning

confidence: 99%

Synthesis, Characterisation, Interaction with DNA, Cytotoxicity, and Apoptotic Studies of Ruthenium(II) Polypyridyl Complexes

et al. 2014

View full text Add to dashboard Cite

We report the synthesis and characterisation of two new ruthenium(II) polypyridyl complexes containing monodentate ancillary ligands [Ru(L) 4 (4HEPIP)], where L ¼ 4-aminopyridine (1) or pyridine (2) and 4HEPIP ¼ 2-(4-hydroxy-3-ethoxyphenyl)-1H-imidazo[4,5-f][1,10](phenanthroline). These complexes were characterised by elemental analysis and ultraviolet-visible, infrared, and 1 H NMR spectroscopy. The binding properties of the two complexes towards calf thymus (CT)-DNA were investigated with different spectrophotometric methods, viscosity measurements, and salt dependent studies. Experimental results indicated that the complexes interact with CT-DNA base pairs by intercalation. Upon irradiation at 365 nm, these complexes efficiently cleave pBR322 DNA from super coiled form I to nicked form II. Their cytotoxicity on different cancer cell lines such as A549, Du145, and HeLa was investigated. The IC 50 values are 39.5, 28.3, and 27.3 mM for complex 1, and 55, 67.9, and 47.9 mM for complex 2 respectively. Cellular uptake and apoptosis induced by these complexes was also studied.

show abstract

Reactions of Phenanthraquinone and Retenequinone with Aldehydes and Ammonium Acetate in Acetic Acid Solution¹

Cited by 296 publications

References 0 publications

Fluorometric Determination of DNA Using a New Ruthenium Complex Ru(bpy)2PIP(V) as a Nucleic Acid Probe

Fluorometric Determination of DNA Using a New Ruthenium Complex Ru(bpy)2PIP(V) as a Nucleic Acid Probe

Design and Synthesis of Some Imidazolyl Derivatives: Photophysical Studies and Application in the Detection of Anions

Synthesis, Characterisation, Interaction with DNA, Cytotoxicity, and Apoptotic Studies of Ruthenium(II) Polypyridyl Complexes

Contact Info

Product

Resources

About

Reactions of Phenanthraquinone and Retenequinone with Aldehydes and Ammonium Acetate in Acetic Acid Solution1

Cited by 296 publications

References 0 publications

Fluorometric Determination of DNA Using a New Ruthenium Complex Ru(bpy)2PIP(V) as a Nucleic Acid Probe

Fluorometric Determination of DNA Using a New Ruthenium Complex Ru(bpy)2PIP(V) as a Nucleic Acid Probe

Design and Synthesis of Some Imidazolyl Derivatives: Photophysical Studies and Application in the Detection of Anions

Synthesis, Characterisation, Interaction with DNA, Cytotoxicity, and Apoptotic Studies of Ruthenium(II) Polypyridyl Complexes

Contact Info

Product

Resources

About

Reactions of Phenanthraquinone and Retenequinone with Aldehydes and Ammonium Acetate in Acetic Acid Solution¹