Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers |
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Authors: | Kamil KopeckyDalibor Šatinský Veronika NovakovaMiroslav Miletin Antonín SvobodaPetr Zimcik |
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Affiliation: | a Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic b Department of Analytical Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic c Department of Biophysics and Physical Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic |
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Abstract: | Mono-, di-, tri- and tetracarboxy-substituted metal-free azaphthalocyanines (AzaPc) were synthesized from 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile and 6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid using a statistical condensation approach. AzaPc bearing eight diethylamino peripheral substituents was also isolated from the mixture. Analysis of the distribution of congeners in the statistical mixture using optimized HPLC method (Phenomenex Synergy RP Fusion column, acetonitrile/tetrahydrofuran/water (pH 5.5) 50:20:30) was performed. The analysis showed optimal ratios of starting materials to be 3:1 for AAAB, 1:3 for ABBB and 1:1 for AABB/ABAB types of the congeners. The distribution of the congeners corresponded well with calculated values indicating similar reactivity of both starting materials and no sterical constraint between adjacent isoindole units in the AzaPc ring. All investigated AzaPc showed no fluorescence, extremely low singlet oxygen quantum yields (Φ? < 0.005) in monomeric form and strong absorption in a wide range from 300 nm to almost 700 nm. Such properties are highly promising for future investigation of these compounds as dark quenchers of fluorescence in DNA hybridization probes. |
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Keywords: | Dark quencher Fluorescence HPLC Phthalocyanine Singlet oxygen Tetrapyrazinoporphyrazine |
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