Synthesis and biological properties of selenium- and tellurium-containing dyes

A Synthetic Route to 3‐(Heteroaryl)‐7‐hydroxycoumarins Designed for Biosensing Applications

“…By analogy with the recent work of Conley et al on the synthesis and bioluminescence properties of a selenium analog of firefly D ‐luciferin,26 we hypothesized that this atom replacement [Se instead of N/S of already known 3‐(heteroaryl)‐7‐hydroxycoumarins] would result in a redshift of the absorption/emission maxima of the fluorescent heterocyclic scaffold. Although there is growing interest in the synthesis of organoselenium‐based molecular dyes and their applications, particularly in photodynamic therapy (PDT) or as fluorescent probes for the detection of various endogenous (bio)analytes in physiological systems,27 this selenium‐containing coumarin dye has never been reported in the literature. Commercially available bis(2‐aminophenyl)diselenide was treated with 7‐acetoxy‐3‐formylcoumarin under the same conditions as described above, to give the target 3‐(2‐benzoselenazolyl)‐7‐hydroxycoumarin (i.e., 18 ), which was isolated by conventional silica gel column chromatography in a modest 14 % yield.…”

Synthesis and properties of a novel alkylselenium substituted phthalocyanine

“…5 However, only few phthalocyanines have been synthesized using this strategy. 6,7 We have recently reported the synthesis and photophysical and photobiological studies of four isosteric water-soluble cationic zinc(II) phthalocyanines by using human nasopharynx KB carcinoma cells.…”

“…6,7 On the other hand, it has been established that several bioactive selenium-based compounds show a large spectra of biological activities. 5,[8][9][10] However, alkylselenium substituted dyes have received less attention than oxygen or sulfur analogous molecules. To our knowledge, only porphyrins replaced with alkylselenium groups have been synthesized, but no alkylselenium phthalocyanines have been reported.…”

“…To our knowledge, only porphyrins replaced with alkylselenium groups have been synthesized, but no alkylselenium phthalocyanines have been reported. 5,[11][12][13][14][15] Based on these results, further studies have been initiated to investigate the synthesis and spectroscopic properties of a novel selenium derivatized zinc(II) phthalocyanine complex to evaluate its properties as a potential photosensitizer for clinical purposes.…”

“…Phthalocyanine 5 was readily prepared by cyclotetramerization of phthalonitrile 4 by using 1,8diazabicyclo [5.4.0]undec-7-ene (DBU) in butanol and zinc acetate at 150 o C. This dye was purified by chromatography, followed by recrystallization to attain 22% of the desired 2(3), 9(10),16(17),23(24)-tetrakis(butylselanyl)phthalocyaninatozinc (II) (5). With regard to the solubility of phthalocyanine 5, is soluble in almost all organic solvents.…”