Methine Cyanine Dyes Research Articles

Polymethine cyanine dyes: Synthesis, cytotoxic activity, and molecular docking study

Virtually, an efficient synthetic procedure was adapted to synthesize new methine cyanine dyes 3–22 from N-arenium salt 2 which was synthesized from the reaction of 1,6-dibromohexane, and 2-benzylpyridine in the presence of dry toluene. Cytotoxicity effects of the synthesized methine cyanine dyes were estimated against two cancer cell lines, HepG2 (liver), MCF-7 (breast), and two normal cells, WI‐38 (human lung fibroblasts), and Vero cells (kidney epithelial cells) as well. All compounds showed cytotoxic activity surpassing the reference 5‐fluorouracil. Of them, compounds 3, 12, 13, 14, and 17 revealed a slight cytotoxic effect on the two normal cells. Moreover, by means of molecular docking, the effectiveness of our compounds towards AKT1 has been studied as it exerts a pivotal role in cell growth, proliferation, survival, and metabolism. All the studied compounds showed good binding mode as well as good binding energy into the pocket of Akt. Thus, highlighting their usefulness as up-and-coming candidates for further preclinical studies.

Antimicrobial and Dyeing Studies of Some Novel Reactive Mono(bis mono), Tri(bis tri) Methine Cyanine Dyes based on Cyano Pyridazine Nucleus

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Oxonium Salts in the Synthesis and Spectral Behavior of Pyrano(pyrylium)‐mono methine Cyanine Dyes

Pyrano‐ and pyrylium mono‐8[4(1)] and/or 5(6)‐[2(4)]methine cyanine dyes (6a–k, 7a–f) were synthesized based on acyclic heterocyclic Schiff bases of pyrolo[3,2‐d]pyrazole[oxazole(imidazol‐6‐one)]‐1‐ium iodide salts, 5‐acetyl‐N‐aryl[pyrazolinyl(pyridinyl)]pyrolo‐[5,4‐d]pyrazolin‐iodide salts, and/or (anhydro bases) precursors (1a–i, 2a–I, 3a–i, 4a–i, and 5A,Ba–i). The structure of pyrylium‐9‐chloride and/or iodide and their pyrano(pyrylium)‐mono‐8[4(1)] and 5(6)[2(4)]methine cyanine dyes was identified by elemental and spectral data. The absorption spectra of some selected dyes were investigated in 95% EtOH, polar (nonpolar) organic solvents and in universal buffer solutions to investigate the optimal conditions for the application of such dyes as photosensitizers.

Synthesis and Photophysical Properties of Novel Highly Stable Zero/Bis-Zero Methine Cyanine Dyes Based on N-Bridgehead Heterocycles

Cyanine dyes of zero/bis-zero methine incorporating imid-azo(1,2-a)Pyridine (quinoline) or pyrazino(1,2-a)pyridine (quinoline) with stable C-N bond were synthesized using keto-oxime methylene C-link heterocyclic quaternary salts [1-phenyl-3-methyl-pyrazolino-4-keto-oxime-α-methylene-bis-pyridin-(quinoin)-1(4)-di-ium-iodide(ethiodide) salts and 1-phenyl-3-methyl-pyrazolino- 4-ketooxime-α-methylene-N-2-methyl-bis pyridin (quinoin)-1(4)-di-ium-iodide(ethiodide) salts]. Such heterocyclic precursors and related dyes were identified by elemental and spectral analyses. The absorption spectra properties of such dyes were investigated in 95% Ethanol to attempt and throw some light on the influence of such new heterocyclic nuclei and to compare or evaluate spectral behaviors. The absorption spectra of dyes in different pure solvents were examined in the visible region showing solvatochromism and the colour changes of dyes with solvents having different polarities. This permits a selection of the optimal solvent (fractional solvent) when such dyes are applied as photosensitizers. The spectral behavior of some selected newly synthesized cyanine dyes is observed in mixed solvents of different polarities and progressively increasing quantities of one solvent over the other were studied and showed an increase in the absorbance of CT band with increasing proportion of that solvent. Evidence for hydrogen bond formation between the solute molecules and solvent molecules allows measurement of certain energies such as hydrogen bonding, orientation, and free energies.

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.

ChemInform Abstract: New 1,3,4‐Oxadiazinoisoquinoline Methine Cyanine Dyes: Synthesis, Photosensitivity and Antibacterial Activity.

AbstractNovel heterocyclic ring systems bearing an 1,3,4‐oxadiazinoisoquinoline moiety are synthesized and utilized as precursor for the preparation of the title dyes.

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.

New 1,3,4‐Oxadiazinoisoquinoline Methine Cyanine Dyes: Synthesis, Photosensitivity and Antibacterial Activity

New heterocyclic ring system including 1,3,4‐oxadiazino[6,5‐c]isoquinoline was prepared and employed as a precursor for preparation of monomethine and trimethine cyanine dyes. The structure of the new compounds was characterized via elemental analysis and mass, 1H‐NMR, and 13C‐NMR spectroscopy. The photosensitivity (electronic transitions inside the dye molecule due to photon absorption) of the new methine cyanine dyes was investigated by studying their visible spectra in absolute ethanol and showed its maxima in the visible range of the spectrum with relatively strong absorption bands. The antibacterial activity of the newly synthesized compounds was evaluated against some bacterial strains, resulting in a promising antibacterial efficacy that recommend the tested compounds as new candidates for further pharmaceutical evaluations.

Some studies in cyanine dyes incorporating pyridine rings endowed with pharmaceutical potency

We report the synthesis of new series of methine cyanine dyes 1, 3–13which have been obtained by the one-pot step reaction of quaternized heterocyclic compound 2 with benzenaminium salt 1 under various methodology technique. (E)-N-(((E)-2-Chloro-3-((phenylamino)methylene)cyclopent-1-enyl)methylene) benzenaminium chloride (1) was synthesized by the reaction of cyclopentanone with Vilsmeier-Haack reagent, then a mixture of an equimolar ratio of aniline: ethanol (1:1) was added to give the target compound. All the synthesized compounds were subjected to in vitro anticancer screening against two cell lines, human cervix carcinoma cell line and human breast carcinoma cell line. Some of these compounds were found to be equipotent or more potentthan commercial anticancer as an evident from the results.

Effects of chemical structure, solvent and solution pH on the visible spectra of some new methine cyanine dyes

Some new dimethine and bis -dimethine, cyanine dyes derived from benzo[2,3-b; 2`,3`-b`] bis -pyrazolo[4,5- b ]-l,4-(oxa-, thia-, and pyra-)-zine-6,12-dione were synthesized. Effect of chemical structure on the electronic visible absorption spectra of all the synthesized cyanine dyes was investigated in 95% ethanol solution. Effects of solvent and/or solution pH on the electronic visible absorption spectra of some selected synthesized cyanine dyes were also examined in pure solvents having different polarities and/or in aqueous universal buffer solutions, respectively. Structural confirmations were carried out through elemental analysis, mass spectroscopy, IR and 1 H NMR spectra.

Utility of quaternary ammonium salts in synthesis of some novel cyanine dyes as potential antibacterial and antitumor agents

A novel class of quaternary ammonium salts has been synthesized in high yield by a convenient procedure which cleanly afforded a new series of methine cyanine dyes 5–11. Structural spectral studies were carried out via measuring the electronic visible absorption spectra of these dyes in DMF. Structural confirmations were determined through elemental analysis, IR, 13C NMR, 1H NMR spectroscopy and mass spectral data. The newly synthesized compounds were screened for their antibacterial and antitumor activity. Among all the tested compounds, it was found that compound 5 revealed better activity against Gram positive rather than Gram negative bacteria. Also, compound 5 showed better activity as antitumor agent.

Syntheses and nonlinear absorption of novel unsymmetrical cyanines

A new synthetic strategy for the generation of methine cyanine dyes with asymmetrical structures has been developed based on a modified Vilsmeier reaction and the condensation reaction of indoline derivatives with organic pyridinium iodide or 4-diphenylamino-benzaldehyde. The nonlinear absorption of some cyanines has been measured using the Z-scan technique.

Synthesis and Spectral Behaviour of Some New Uninuclear Pyrimidine 2[2(4)]-Mono(Tri)-Methine Cyanine Dyes

New unsymmetrical 2[2(4)]-mono-and tri (substituted tri)-methine cyanine dyes incorporating 1,2,5,6-tetrahydro-4,6-diaryl pyrimidine (pyrimidinium-1-yl salt)-2-one were prepared. Structural determination was carried out by elemental analysis, IR and 1H NMR spectral data. The spectral behaviour of all the synthesized cyanines was examined in 95% ethanol.

Synthesis and solvatochromic behaviour of new asymmetrical mono-(tri)-methine cyanine dyes

6-Amino-5-cyano-3-methyl-1,4-diarylpyrano[2,3-c]pyrazole derivatives were prepared via the interaction ofα, β-unsaturated nitriles with 3-methyl-1-phenylpyrazol-5-one as starting materials in the synthesis of new asymmetrical mono-(tri)-methine cyanine dyes. The new cyanines were characterised by elemental analysis, IR and1H-NMR spectral data. The visible absorption spectra of some selected dyes were investigated in pure and mixed solvents as well as in aqueous buffer solutions.

ChemInform Abstract: Syntheses and Electronic Absorption Spectra of Some New Penta‐ and Di‐ Methine Cyanine Dyes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 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.

Heterocyclic halide moieties in the synthesis and study of some conjugated oxazine methine cyanine dyes

New asymmetrical/symmetrical styryl cyanines (3a–d,4a–d), monomethine cyanine dyes (5a–d,6a–d) and trimethine cyanine dyes (11a–g,12a–g) incorporatingbis pyrazolo-[2,3-b;2′,3′-b′] oxazine and/or pyrazolo [2,3-b]-oxazolo [2′,3′-b] oxazine were prepared. The new synthesised cyanines were identified by elemental and spectral analyses. The uv-visible absorption spectra of some selected dyes were investigated in pure and mixed solvents as well as in aqueous buffer solutions. Molecular complex formation with ethanol was verified by mixed solvent studies. Electronic transitions were attributed to either locally excited or predominantly charge transfer states. The spectral shifts were discussed in relation to molecular structure and in terms of medium effects. The variation of absorbance withpH was utilized for the determination of thepKa values for some selected compounds.

Electronic spectra of some new synthesised methine cyanine dyes

New methine cyanine dyes such as monomethine (3a–e), azamethine (4a–c) and trimethine (6a–i) and (8a–c) incorporating a fused pyrazolo [3,4-d] oxazole nucleus were prepared. The new synthesised cyanines were identified, by elemental and spectral analyses. The visible absorption spectra of some selected dyes were investigated in pure and mixed solvents as well as in aqueous buffer solutions. Molecular complex formation with ethanol was verified by mixed solvent studies. The variation of absorbance withpH was utilized for the determination of thepKa values for selected compounds.

SYNTHESIS OF ASYMMETRICAL 2(3)-OXASOLINO (PYRAZOLINO)- 2(4)-METHINE CYANINE DYES

Synthesis of new types of asymmetrical-2(3)-oxazolino - (pyrazolino)-4,3-b)-quinoline-2(4)- methine cyanine dyes including mono-, di-,trimethine cyanines (IVa-d,V,VIl a,b and IXa-d) was achieved by interaction of 4-hydroxy-2(3)-methyl oxazololino (pyrazlino)-4,3-b)-quinoline (la,b) with active components. The new cyanines were identified through IR and 1H NMR spectra. The electronic absorption spectra of the dyes in the visible region is reported. Bactericidal activty of selected cyanine dyes (IVa,IVd,V,VII6,1Xc) were tested against some bacterial strains.

ChemInform Abstract: Synthesis and Electronic Spectra of Some Bisheterocyclic Methine Cyanine Dyes.

AbstractThe pyrazolopyrazoles (Ia), (Ib), and the pyrazoloxazole (Ic) react with ethyl iodide (II) to produce the pyrazolium salts (III).

Synthesis and electronic spectra of some bis-heterocyclic methine cyanine dyes

New asymmetric and symmetric pyrazolo[3,4-d]pyrazole (and isoxazole) methine cyanines of the monomethine, azomethine and trimethine type were prepared. The new new dyes were characterised by IR and 1H-NMR spectral data. The electronic spectra data of the dyes are discussed.