Extending the Class of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

Abstract

Synthetic routes to a collection of new fluorescent dyes are described, which are based on the [1,3]‐dioxolo[4.5‐f]benzodioxole (DBD) core. By introducing different electron withdrawing groups in 4‐ and 8‐position of the DBD moiety the emission wavelength could be adjusted over a large spectral range from blue to orange light.

Detection of dsDNA with [1,3]Dioxolo[4,5‐f]benzodioxol (DBD) Dyes

“…Flash chromatography was carried out on silica gel 60 (40-63 mm). NMR spectra were recorded with aB ruker Avance 300 spectrometer.C hemical shifts are reported relative to the solvent signal Benzo [1,2-d:4,5-d']bis [1,3]dioxole-4-carbaldehyde (1):T his compound was prepared according to reference [9].…”

“…The structuralu nits that are expected to promote DNA binding of the concept Bp rototype are the amidinium groups. We started the synthesis from DBD parentc ompound 4, [9] represented in Scheme 2. The 3-(4-cyanophenyl)propionyl group could be introducedv ia their Weinreb amide 5,y ielding 45 % of the monosubstituted amidinium precursor 6 and 17 %o f disubstituted product 7 [(i)M ethod a].W ef ound, that the synthesis of the monoderivative 6 could be further improved by employing procedure (i)M ethod b( 61 %y ield) and thus decided to aim for both models: ad ye with two amidinium moieties and ad ye with only one such dsDNA bindingg roup.…”

“…was prepared according to reference [27]. (3):C ompounds 1 (50 mg, 0.26 mmol, 1.0 equiv), 2 (108 mg, 0.38 mmol, 1.5 equiv) and pyridine (0.03 mL, 0.37 mmol, 1.0 equiv) were dissolved in anhydrous methanol (5 mL) and heated to reflux for 9h.T he precipitate product was fil- [1,3]dioxole (4):T his compound was prepared according to reference [9].…”

“…Progressh as also been made in utilizingt he DBD chromophorei nt he field of Fçrsterr esonance energy transfer (FRET) [8] and the design of the fluorescencep roperties of the DBD chromophore became increasingly sophisticated. [9] Hence, it appealed to us to expand the variety of biological moleculest hat can interact with the DBD chromophore.W ew ondered whether we would be able to modify our DBD chromophorei ns uch aw ay that their unique features could also be combined with the ability to bind to double-stranded (ds) DNA.…”

“…Applying the DBD dye in various contexts resulted in numerous ways that the DBD chromophore can connect to and interact with biological molecules. Progress has also been made in utilizing the DBD chromophore in the field of Förster resonance energy transfer (FRET) and the design of the fluorescence properties of the DBD chromophore became increasingly sophisticated . Hence, it appealed to us to expand the variety of biological molecules that can interact with the DBD chromophore.…”