Dimethine Cyanine Dyes Research Articles

Synthesis of some novel dimethine, bis-dimethine cyanine dyes and octacosamethine cyanine dyes endowed with promising biological potency against (HepG2), (Hela), (MCF-7), (MIA), (SN12C) and (H358) cell lines

Successfully, one step two component synthesis of dimethine cyanine dyes, bis-dimethine cyanine dyes and icosamethine cyanine dyes 2–10via reaction of pyridinium salt 1 with some different aldehydes hope to obtain these compounds with enhanced biological potency as antitumor agents against spontaneous liver (HepG2), cervical (Hela), breast (MCF-7), pancreas (MIA), kidney (SN12C) and lung (H358). The impact of substituted drugs on the tumor cells was reflected by means of structure activity relationship (SAR). Among these dyes, icosamethine cyanine dye 8 recorded an excellent activity toward all the tested cell lines. The newly destined drugs were identified and emphasized by spectroscopy and elemental analyses.

Structure and solvent effects on the electronic transitions of some novel furo / pyrazole cyanine dyes

Novel furo / pyrazole methine cyanine dyes covering dimethine and bis dimethine cyanine dyes derived from quinone polyheterocyclic ring system were prepared. The electronic visible absorption behavior for all the synthesized cyanine dyes were investigated in 95% ethanol solution to evaluate their structure effects on the visible electronic transitions. The dyes were thought to be better electronic transitions when they absorb light at higher wavelength bands (bathochromic shifted and/or red shifted dyes). Consequently, the electronic transitions of the dyes decreases when they absorb light at lower wavelength bands (hypsochromic shifted and/or blue shifted dyes). Solvent effects for some selected synthesized cyanine dyes were examined in pure solvents having different polarities [Water (78.54), Dimethylformamide (36.70), Ethanol (24.3), Chloroform (4.806), Benzene (2.28) and Dioxane (2.209)] to evaluate solvent effects on their visible electronic transitions (general and/or specific solvent effects). Structural identification were confirmed via elemental analysis, visible spectra, IR and 1H NMR spectral data.

Synthesis, spectral behavior and biological activity of some novel 1,3,4-oxadiazine cyanine dyes

New methine cyanine dyes covering monomethine cyanine dyes and dimethine cyanine dyes derived from benzo[(2,3-b)benzoxazine; (2,3-e)1,3,4-oxadiazine]-5,12-dione were prepared. The electronic visible absorption spectra of all the synthesized cyanine dyes were investigated in 95% ethanol solution. Biological activity for a number of selected compounds was tested and evaluated against various bacterial strains ( Bacillus subtilis , Escherichia coli , Pseudomona aeruginosa and Staphylococcus aureus ). Structural determination was carried out via elemental analysis, visible, mass, IR and 1 H NMR spectroscopic data.

Synthesis, crystal structures, and spectral properties of double N-alkylated dimethine cyanine dyes and their interactions with biomolecules and living cells

A series of new doubleN-alkylated dimethine cyanine dyes were synthesized, and their crystal structures and spectral properties, as well as their interaction with biomolecules and living cells, were investigated.

Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

A series of dimethine cyanine dyes, used as fluorescent probes, were synthesized under microwave irradiation, and identified by 1H NMR, IR, elemental analysis and HRMS. The investigation of their spectral properties in phosphate-buffer saline (PBS) showed that the absorption and emission maxima of the dyes were in the region 370–480 nm and 471–569 nm, respectively. The properties of the dyes as fluorescent probes for living cells imaging and flow cytometry were investigated. The results showed that dyes 1, 2, 8 or 9 could penetrate an intact cell membrane, stained the cell nuclear and exhibited bright fluorescence. Little background interference, low cell cytotoxicity and little photobleaching were showed during the imaging tests. The dyes 1, 8 and 9 could be applied in flow cytometry and dye 1/PI, dye 8/PI or dye 9/PI couple could be proposed as double staining agents to measure sperm cell viability. Thus the dyes represented the cell-permeant fluorescent probes.

Synthesis of Different Classes of Five / Five Membered Heterocyclic Cyanine Dyes: A Review Paper

The paper reviews synthesis of different classes of biheterocyclic five/five membered heterocyclic cyanine dyes. In this review paper detailed synthesis steps for some of the biheterocyclic five/five membered cyanine dyes were represented by equations. The synthesis covers, monomethine cyanine dyes (simple cyanine dyes), aza-monomethine cyanine dyes, dimethine cyanine dyes, trimethine cyanine dyes (carbocyanine dyes), aza-trimethine cyanine dyes, tetramethine cyanine dyes, heptamethine cyanine dyes (tricarbocyanine dyes), styryl cyanine dyes (hemi cyanine dyes), aza-styryl cyanine dyes (aza-hemi cyanine dyes) and apocyanine dyes. In addition, in the introduction section we shed some light on the use and applications of cyanine dyes. Keywords: Cyanine dyes, synthesis, five/five membered cyanine dyes, application of cyanine dyes, uses of cyanine dyes, ESA, Pyridine, Cyanomethylene, Diphenylformamidine, triethoxymethane

Synthesis, absorption and fluorescence spectral characteristics of trinucleus dimethine cyanine dyes as fluorescent probes for DNA detection

The preparation of six trinucleus dimethine cyanine dyes with pyridine nucleus obtained by the condensation of trimethylpyridinium iodides with heterocyclic aromatic aldehyde was described. The absorption and fluorescence properties of the dyes were studied in different polarity solvents. Blue shift of the maxima absorption of the dyes was observed with the increase of solvents polarity. The fluorescence properties of the dyes in solution and in presence of DNA were studied. Significant enhancement of the fluorescent quantum yield was observed in four dyes in the presence of DNA. Specially, one of six dyes emitted weak fluorescence in Tris-HCl buffer, but displayed bright fluorescence in the presence of DNA.

ChemInform Abstract: Studies on the Synthesis of Conjugated Five-Membered Bisheterocyclic Dimethine Cyanine Dyes.

ChemInform Abstract: Studies on the Synthesis of Conjugated Five-Membered Bisheterocyclic Dimethine Cyanine Dyes.

The absorption, emission spectra as well as ground and excited states calculations of some dimethine cyanine dyes

The absorption and emission properties as well as electronic structure in the ground ( S 0) and excited states ( S 1) of seven dimethine cyanine dyes were investigated by time dependent density functional theory (TD-DFT) and configuration interaction singles (CIS) levels. The effect of water on the absorption and emission spectra of the dyes was taken into account using the polarizable continuum model (PCM). TD-DFT calculations provided a correct description of the electronic absorption spectra and showed that the dominant transitions of seven dye molecules presented a π–π* character. Scaling factor 0.72 was used on the absorption and emission wavelengths obtained by CIS method, and the scaled emission wavelengths were in good agreement with the experimental values. Compared with experimental counterparts, the average relative deviations of the absorption and emission maxima were about −2.4% and 1.7%, respectively.

ChemInform Abstract: Microwave‐Assisted Solvent‐Free Synthesis of Some Dimethine Cyanine Dyes, Spectral Properties and TD‐DFT/PCM Calculations.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Microwave-assisted solvent-free synthesis and spectral properties of some dimethine cyanine dyes as fluorescent dyes for DNA detection

A series of dimethine cyanine dyes were synthesized in a fast, efficient and high yield by the condensation of quaternary salts with 1 H-indole-3-carbaldehyde in the presence of piperidine under solvent-free microwave irradiation. The products were identified by 1H NMR, IR, UV–vis spectroscopy and elemental analysis. The absorption and fluorescence properties of the dyes in both the free state and DNA or BSA were investigated. Significant enhancement of the fluorescent quantum yield was observed for all the dyes in the presence of DNA, with one compound demonstrating excellent sensitivity as a fluorescent probe.

Microwave-assisted Solvent-free Synthesis of Some Dimethine Cyanine Dyes, Spectral Properties and TD-DFT/PCM Calculations

A series of dimethine cyanine dyes were synthesized in a fast, efficient and high yield by the condensation of quaternary salts with 1H-indole-3-carbaldehyde in the presence of piperidine under solvent-free microwave irradiation. The products were identified by 1H NMR, IR, UV-Vis spectra and elemental analysis. The absorption and fluorescence properties of these dyes were investigated both experimentally and theoretically. Calculations performed at a combination of time-dependent density functional theory (TD-DFT) and the polarizable continuum model (PCM) reproduced the π-π* type absorption bands of the dyes. Regression analysis was used for studying theoretical results of the absorption maxima in different solvents. Compared with experimental counterparts, estimated overall uncertainties in the absorption maxima were about ±2%.

Synthesis and Visible Spectral Behaviour of Some New Photosensitizers: Monomethine, Dimethine, Trimethine, Styryl and Mixed Cyanine Dyes

The new photosensitizers, monomethine, dimethine, trimethine, styryl and mixed cyanine dyes incorporating pyrazolo/oxazole(thiazole) nuclei are prepared; the visible absorption spectra for all the synthesized cyanines were examined in 95% ethanol; structural confirmation is carried out by elemental analysis, IR and 1H NMR spectroscopy.

Synthesis and Visible Spectral Behaviour of Some New Photosensitizers: Monomethine, Dimethine, Trimethine, Styryl and Mixed Cyanine Dyes

The new photosensitizers, monomethine, dimethine, trimethine, styryl and mixed cyanine dyes incorporating pyrazolo/oxazole(thiazole) nuclei are prepared; the visible absorption spectra for all the synthesized cyanines were examined in 95% ethanol; structural confirmation is carried out by elemental analysis, IR and 1H NMR spectroscopy.

Heterocycles as donor and acceptor units in push–pull conjugated molecules. Part 1

The synthesis and spectroscopic investigation of a number of push–pull ethenes in which the donor moiety is represented by a π-excessive five-membered heterocycle (pyrrole, indole and thiophene) and the acceptor group is a π-deficient heterocyclic azine ring (pyridine, pyrazine, pyrimidine, pyridazine) are described. The intramolecular charge transfer in both the neutral compounds and the corresponding N-alkylpyridinium triflates is discussed and confirmed on the basis of three different descriptors, ΔλHetPh,Δλ+n, and Δλsolv1solv2, that take into account the substitution of a phenyl with a heterocyclic donor ring, charge effects and solvatochromism, respectively. According to the ΔλHetPh descriptor, the intramolecular charge transfer in the described diheteroarylethenes increases upon increasing the electron-withdrawing capacity of the acceptor, sustained by the presence of either more than one nitrogen atom or the positive charge in the heterocyclic azine. The described pyridinium derivatives belong to the rarely investigated class of dimethine cyanine dyes. The response of the 13C and 15N NMR chemical shift data appears to be less clear because of the low sensitivity of the NMR probes to remote substitution. © 1997 John Wiley & Sons, Ltd.

Heterocycles as donor and acceptor units in push-pull conjugated molecules. Part 1

The synthesis and spectroscopic investigation of a number of push–pull ethenes in which the donor moiety is represented by a π-excessive five-membered heterocycle (pyrrole, indole and thiophene) and the acceptor group is a π-deficient heterocyclic azine ring (pyridine, pyrazine, pyrimidine, pyridazine) are described. The intramolecular charge transfer in both the neutral compounds and the corresponding N-alkylpyridinium triflates is discussed and confirmed on the basis of three different descriptors, ΔλHetPh,Δλ+n, and Δλsolv1solv2, that take into account the substitution of a phenyl with a heterocyclic donor ring, charge effects and solvatochromism, respectively. According to the ΔλHetPh descriptor, the intramolecular charge transfer in the described diheteroarylethenes increases upon increasing the electron-withdrawing capacity of the acceptor, sustained by the presence of either more than one nitrogen atom or the positive charge in the heterocyclic azine. The described pyridinium derivatives belong to the rarely investigated class of dimethine cyanine dyes. The response of the 13C and 15N NMR chemical shift data appears to be less clear because of the low sensitivity of the NMR probes to remote substitution. © 1997 John Wiley & Sons, Ltd.

Syntheses and electronic absorption spectra of some new penta- and di-methine cyanine dyes

The reaction of a ratio of 1 mole of 5-chloro-3-methyl-1-phenyl pyrazolo-4[2(4)]-dimethine cyanine (1a,b) or (5-chloro-4-formyl-3-methyl-1-phenylpyrazole) 2 with 2 moles of an appropriate 2(4)-heterocyclic quaternary salt afforded the novel pentamethine cyanine dyes (3a–3e). Other reactions of 2 with heterocyclic nitrogen bases, followed by condensation of the newly formed quaternary nitrogen salts (4a–4c) with methoheterocyclic iodide salts provided the corresponding unsymmetrical dimethine cyanine dyes (5a–5g). The new pentamethine and dimethine cyanine dyes were identified by elemental analyses and IR and 1H-NMR spectral data. The visible absorption spectra of some selected dyes were investigated in pure and mixed solvents as well as in universal buffer solutions. The measure of the variation of absorbance with pH was utilized for the determination of the pKa values for compounds 3b, 3d, 3e, 5e, and 5f, and these data are discussed. © 1997 John Wiley & Sons, Inc. Heteroatom Chem 8: 259–266, 1997.

Synthesis and properties of some naphtho (quinolino)-quinone heterocyclic dimethine cyanine dyes

Some new asymmetrical naphtho-/quinolinoquinone [2, 3- d]-thiazole-4, 9-dione and/or [2, 3- e] oxadiazine 5, 10-dione dimethine cyanine dyes have been prepared. Their solvatochromic and spectral behaviour in buffer solutions has been utilized to select the optimum solvent and pH value at which they might be applied as photosensitizers. Some of the dyes have been tested for their antimicrobial activity.

Electronic absorption spectral studies on new dimethine cyanine dyes

New asymmetrical dimethine cyanine dyes were prepared by the condensation of 4-benzylideno-oxazol-/imidazol-5-one-2-carboxaldehyde derivatives with 2-methylpyridinium(quinolinium)-2-yl salts. Cyclocondensation reaction of these dyes with urea gave new asymmetrical oxazolo(imidazo)-[4,5-d]-pyrimidine-2(2)-dimethine cyanines. The ultraviolet and visible absorption spectra of some selected dyes were investigated in single and mixed solvents, and also in aqueous buffer solutions. Molecular complex formation with ethanol was verified through mixed-solvent studies. Electronic transitions have been attributed to either locally excited or predominantly charge- transfer states. The spectral shifts are discussed in relation to molecular structure and in terms of medium effects. The variation of absorbance with pH is utilised for the determination of pKa. values for some selected compounds.

ChemInform Abstract: Synthesis and Spectra of Pyrazolo(4,5‐b)pyrido(2,3‐c)pyrazine Dimethine Cyanine Dyes.

AbstractThe diaminonitrosopyridine (I) undergoes cyclocondensation with the methylpyrazolone derivatives (II) to form the pyrazolopyridopyrazines (IIIa) and (IIIb).