New Synthetic Approach to Aminosquarylium Cyanine Dyes

Reis, Lucinda V.; Serrano, J. P. C.; Almeida, P.; Santos, Paulo F.

doi:10.1055/s-2002-34226

Cited by 6 publications

(7 citation statements)

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“…of highly reactive methylating agent methyl trifluoromethanesulfonate (MeOTf) in dehydrated dichloromethane (CH 2 Cl 2 ) at 25 °C overnight produced O-methylated SQ dye 3 b with a triflate (TfO À ) counter anion in 24 % yield (Scheme 2, eq.1), according to the previous method. [10] The UV-vis-NIR spectra and photographs of the four synthesized SQ dyes 2 a, 2 b, 3 b, and 4 b in CH 2 Cl 2 (3 × 10 À 6 M) are shown in Figure 2(a). The maximum absorption wavelength (λ max ) and calculated molar absorption coefficient (ε) are presented in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Highly Photostable Benzoindolenine‐Based Squaraine Dyes by using Aromatic Fluorine Atoms

et al. 2023

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We have elucidated the details of the photodegradation of non‐fluorinated benzoindolenine‐based SQ dyes with low photostability in solution and proposed a hypothesis to improve their photostability. Based on the results, replacing all the hydrogen atoms on the benzoindolenine ring with fluorine atoms or methylation of the oxygen anions of the non‐fluorinated benzoindolenine SQ dye resulted in improvement of photostability. Furthermore, a preliminary investigation of the synthesized SQ dyes for organic photovoltaics revealed that the O‐methylated SQ dye with bulky fluorine‐containing anions provided a much higher Voc than similar benzoindolenine‐based SQ dyes.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Highly Photostable Benzoindolenine‐Based Squaraine Dyes by using Aromatic Fluorine Atoms

et al. 2023

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“…The synthesis of unsymmetrical molecules, in the case of the dyes presented in this study, aimed at combining photophysicochemical properties which, according to some of our previous works, would be of particular interest in the formulation of novel photosensitizer candidates for photodynamic cancer therapy. The choice of quinoline and benzoselenazole heterocycles was based on the fact that the dyes with quinoline units display a much higher red shift in their absorption than other heterocycle nuclei [39], and those of benzoselenazole, as it has a heavy atom in their structure, can positively influence the production of reactive oxygen species by the so-called "heavy atom effect" [40].…”

Section: Discussionmentioning

confidence: 99%

“…The latter reacted with the benzoselenazole-based quaternary ammonium salt 8 in a n-butanol and pyridine refluxing mixture to afford the zwitterionic unsymmetrical squaraine dye 9. The methylation reaction of this latter dye with the strong methylating agent methyl trifluoromethanesulfonate, in anhydrous conditions, allowed us to obtain the O-methyl ether intermediate dye 10 [39,42] with good yield. In the last step of the synthetic approach, two aminosquaraines dyes, 11 and 12, were prepared through a nucleophilic reaction of the O-methyl derivative methoxy group by ammonia and methylamine solutions, respectively [25,42].…”

Section: Dyes' Synthesis Strategymentioning

confidence: 99%

“…To that end, several squaraine cyanine dyes, commonly named as squaraine or squarylium dyes, a family of synthetic dyes first-synthesized in the 1960s [35], have been the subject of photodynamic studies [25,36,37] given their relevant photochemical and photophysical properties [38][39][40]. These dyes are known to possess good photoconductivity, great stability under light exposure, and narrow and intense absorption bands within the tissue transparency spectral region [38,41], singlet oxygen production and high molar absorption coefficient [42].…”

Section: Introductionmentioning

confidence: 99%

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Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines

et al. 2020

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Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity.

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“…As sulfur homologues, selenium-containing compounds, especially benzoselenazoles, have recently found several uses in materials science, organic synthesis and medicinal chemistry [17][18][19][20][21]. The exchange of sulfur to a selenium atom could lead to the desired red shift in the absorption and emission spectra [22]. Even based on these limited reports, it is clear that benzoselenazolium-based cyanine dyes can identify nucleic acids in cells.…”

Section: Introductionmentioning

confidence: 99%

Selenium-Substituted Monomethine Cyanine Dyes as Selective G-Quadruplex Spectroscopic Probes with Theranostic Potential

Fabijanić

Kurutos²,

Paić³

et al. 2023

Biomolecules

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The binding interactions of six ligands, neutral and monocationic asymmetric monomethine cyanine dyes comprising benzoselenazolyl moiety with duplex DNA and RNA and G-quadruplex structures were evaluated using fluorescence, UV/Vis (thermal melting) and circular dichroism (CD) spectroscopy. The main objective was to assess the impact of different substituents (methyl vs. sulfopropyl vs. thiopropyl/thioethyl) on the nitrogen atom of the benzothiazolyl chromophore on various nucleic acid structures. The monomethine cyanine dyes with methyl substituents showed a 100-fold selectivity for G-quadruplex versus duplex DNA. Study results indicate that cyanines bind with G-quadruplex via end π-π stacking interactions and possible additional interactions with nucleobases/phosphate backbone of grooves or loop bases. Cyanine with thioethyl substituent distinguishes duplex DNA and RNA and G-quadruplex structures by distinctly varying ICD signals. Furthermore, cell viability assay reveals the submicromolar activity of cyanines with methyl substituents against all tested human cancer cell lines. Confocal microscopy analysis shows preferential accumulation of cyanines with sulfopropyl and thioethyl substituents in mitochondria and indicates localization of cyanines with methyl in nucleus, particularly nucleolus. This confirms the potential of examined cyanines as theranostic agents, possessing both fluorescent properties and cell viability inhibitory effect.

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New Synthetic Approach to Aminosquarylium Cyanine Dyes

Cited by 6 publications

References 0 publications

Synthesis of Highly Photostable Benzoindolenine‐Based Squaraine Dyes by using Aromatic Fluorine Atoms

Synthesis of Highly Photostable Benzoindolenine‐Based Squaraine Dyes by using Aromatic Fluorine Atoms

Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines

Selenium-Substituted Monomethine Cyanine Dyes as Selective G-Quadruplex Spectroscopic Probes with Theranostic Potential

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