Synthesis of new azaphthalocyanine dark quencher and evaluation of its quenching efficiency with different fluorophores |
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| Authors: | Kamil KopeckyVeronika Novakova Miroslav MiletinRadim Ku?era Petr 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 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: | New unsymmetrical zinc azaphthalocyanine (AzaPc) was synthesized using statistical condensation of two precursors. Postsynthetic modifications led to incorporation of azide group that efficiently underwent Cu(I)-catalyzed azide/alkyne 1,3-dipolar cycloaddition with terminal alkyne on a solid phase. The modified solid phase was then used for synthesis of oligodeoxyribonucletides labeled with AzaPc. DNA hybridization assays confirmed high quenching efficiency (QE>96%) of zinc AzaPc quencher with six different fluorophores ranging in emission maxima from 517 nm to 701 nm (FAM, HEX, Cy3, Cy3.5, Cy5, and Cy5.5). |
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| Keywords: | Phthalocyanine Tetrapyrazinoporphyrazine Dark quencher Hybridization Fluorescence Click chemistry |
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