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Synthesis of a Photostable Energy‐Transfer Pair for “DNA Traffic Lights”
Author(s) -
Bohländer Peggy R.,
Wagenknecht HansAchim
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403119
Subject(s) - cyanine , chemistry , fluorescence , dna , energy transfer , oligonucleotide , photochemistry , combinatorial chemistry , nanotechnology , chemical physics , optics , biochemistry , physics , materials science
Abstract A new cyano‐substituted thiazole red derivative as a red emitter and a novel green fluorescent donor dye of the cyanine styryl type were synthesized in good yields. Characterization of their optical properties revealed excellent photostabilities and large apparent Stokes' shifts. Both dyes can be incorporated into oligonucleotides through postsynthetic “click”‐type chemistry and combined in a diagonal arrangement in double‐stranded DNA. As a result, both dyes combine to an energy‐transfer pair in DNA that shows remarkable optical properties such as significant emission wavelength shift from green to red upon hybridization owing to high energy‐transfer efficiency between the two dyes and remarkable emission red/green color contrast ratio. The combination of these dyes as an energy‐transfer pair according to our concept of “DNA traffic lights” has high potential for applications in molecular imaging.