Journal ArticleDOI
Magnesium azaphthalocyanines: an emerging family of excellent red-emitting fluorophores.
Petr Zimcik,Veronika Novakova,Kamil Kopecky,Miroslav Miletin,Rabia Zeynep Uslu Kobak,Eva Svandrlikova,Lenka Vachova,Kamil Lang +7 more
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TLDR
The described properties show that magnesium(II) AzaPcs are excellent red-emitting fluorophores with potential applications as fluorescent probes in sensing or in vitro imaging applications.Abstract:
Magnesium(II), zinc(II), and metal-free phthalocyanines (Pcs) and azaphthalocyanines (AzaPcs) containing alkylsulfanyl, aryloxy, and dialkylamino peripheral substituents have been synthesized. The complexation of magnesium(II) by metal-free Pcs and AzaPcs has been studied in detail to determine the optimal reaction conditions necessary to ensure a complete conversion. Photophysical and photochemical measurements in tetrahydrofuran showed that magnesium(II) AzaPcs with aryloxy and alkylsulfanyl substituents have excellent fluorescent properties (Φ(F) up to 0.73) and that the corresponding zinc(II) Pcs are efficient singlet oxygen producers (Φ(Δ) up to 0.68). The presence of dialkylamino substituents causes intramolecular charge transfer within the molecule that competes with fluorescence and singlet oxygen formation. Alkylsulfanyl MgAzaPc and ZnAzaPc were the most photostable compounds among the series of studied derivatives. In addition, high molar absorption coefficients (e ∼ 300,000 M(-1) cm(-1)), absorption (λ(max) ∼ 650 nm), and emission (λ(em) ∼ 660 nm, high Φ(F)) in the red region suggest that these molecules are potential fluorescent probes that are superior to the commercial red cyanine dye Cy5. MgAzaPc, when incorporated into lipidic bilayers of liposomes, maintains excellent fluorescence properties (Φ(F) = 0.64). Water-soluble MgAzaPc with quaternary ammonium peripheral substituents retained a high fluorescence quantum yield even in water (Φ(F) = 0.25). The described properties show that magnesium(II) AzaPcs are excellent red-emitting fluorophores with potential applications as fluorescent probes in sensing or in vitro imaging applications.read more
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Journal ArticleDOI
Design, synthesis, and properties of phthalocyanine complexes with main-group elements showing main absorption and fluorescence beyond 1000 nm.
TL;DR: The combination of spectral, electrochemical, and theoretical considerations revealed that all of the central group 15 elements, peripheral group 16 elements, and their positions are necessary to shift the Q-band beyond 1000 nm, indicating that the substitution effects of group 15 and 16 elements act synergistically.
Journal ArticleDOI
Far-red-absorbing cationic phthalocyanine photosensitizers: synthesis and evaluation of the photodynamic anticancer activity and the mode of cell death induction.
Miloslav Machacek,Antonin Cidlina,Veronika Novakova,Jan Svec,Emil Rudolf,Miroslav Miletin,Radim Kučera,Tomas Simunek,Petr Zimcik +8 more
TL;DR: Subcellular changes upon photodynamic treatment of the HeLa cells indicated that the studied photosensitizers induced damage primarily to the lysosomes, which was followed by a relocalization and damage to other organelles, and a predominant involvement of necrosis-like cell death.
Journal ArticleDOI
Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information
TL;DR: Tetrapyrazinoporphyrazines (TPyzPzs) are known since 1937 and were intensively studied especially in the last fifteen years as discussed by the authors.
Journal ArticleDOI
Tetrapyrazinoporphyrazines and their metal derivatives. Part II: Electronic structure, electrochemical, spectral, photophysical and other application related properties
TL;DR: In this article, the synthesis of variously substituted TPyzPzs and their metal complexes as well as of their precursors was presented, with a focus on the related perspectives of practical applications in the fields of nonlinear optical properties, liquid crystals, catalysis, sensors, dark quenchers of fluorescence, photodynamic therapy (PDT), and light harvesting.
Journal ArticleDOI
Direct Transformation of Esters into Heterocyclic Fluorophores.
Christian Fischer,Christof Sparr +1 more
TL;DR: A modular method that converts various carboxylic acid esters directly into a broad spectrum of heteroanthrylium fluorophores is described that provides access to organophotoredox catalysts for dual catalysis with nickel and dyes amenable to fluorescence enhancement.
References
More filters
Journal ArticleDOI
A clearer vision for in vivo imaging.
TL;DR: Progress continues in the development of smaller, more penetrable probes for biological imaging, and the number of probes in this line of research has increased.
Book
Liposomes : a practical approach
TL;DR: Cossins liposomes in biological systems, R.R.C.Jones and A.J.Martin physical methods of study and new liposome characterization.
Journal ArticleDOI
Small-volume extrusion apparatus for preparation of large, unilamellar vesicles
Robert C. MacDonald,Ruby I. MacDonald,Bert Ph. M. Menco,Keizo Takeshita,Nanda K. Subbarao,Lan-rong Hu +5 more
TL;DR: The filter holder provides for back-and-forth passage of the sample between two syringes, a design that minimizes filter blockage, eliminates the need to change filters during LUVET preparation and reduces preparation time to a few minutes.
Journal ArticleDOI
Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters
Ratnakar B. Mujumdar,Lauren A. Ernst,Swati R. Mujumdar,Christopher J. Lewis,Alan S. Waggoner +4 more
TL;DR: A series of new fluorescent labeling reagents based on sulfoindocyanine dyes contain succinimidyl ester reactive groups and can be readily conjugated to antibodies, avidin, DNA, lipids, polymers, and other amino-group-containing materials.