Bis-triazolylchalcogenium-Functionalized Benzothiadiazole Derivatives as Light-up Sensors for DNA and BSA

Abstract

A range of bis-triazolylchalcogenium-BTD 3 was synthesized by a copper-catalyzed azide–alkyne cycloaddition of azido arylchalcogenides 1 and 4,7-diethynylbenzo­[c]­[1,2,5]­thiadiazole 2. Eight new compounds were obtained in moderate to good yields using 1 mol % of copper­(II) acetate monohydrate under mild reaction conditions. In addition, the synthesized bis-triazolylchalcogenium-BTD 3a–3h were investigated regarding their photophysical, electrochemical, and biomolecule binding properties in solution. In general, compounds presented strong absorption bands at the 250–450 nm region and cyan to green emission properties. The redox process attributed to the chalcogen atom was observed by electrochemical analysis (CV techniques). In addition, spectroscopic studies by UV–vis, steady-state emission fluorescence, and molecular docking calculations evidenced the ability of each derivative to establish interactions with calf-thymus DNA (CT-DNA) and bovine serum albumin (BSA). The behavior presented for this new class of compounds makes them a promising tool as optical sensors for biomolecules.

Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3‐triazolyl‐thiazolidines Hybrids

“…This may be attributed to the weak competition of thiazolidine derivatives with the EB dye over the DNA structure. The same behavior has been already reported by some examples [44,45] and this probably non-intercalative mode is confirmed by viscosity analysis.…”

“…Blue or red‐shifts were no observed depending on the substituent. The interactive possibility of these derivatives is probably H‐bonding secondary forces with the DNA bases or the presence of the triazole moiety in the structure that may interact with DNA bases via covalent interactions, as previously reported for other triazole derivatives [43,44] …”

“…The interactive possibility of these derivatives is probably H-bonding secondary forces with the DNA bases or the presence of the triazole moiety in the structure that may interact with DNA bases via covalent interactions, as previously reported for other triazole derivatives. [43,44] Also, the binding constants (K b ) and Gibbs free-energy (ΔG) of the triazole derivatives were calculated (Table 2). In general, all 1,2,3-triazoles derivatives demonstrated moderate binding forces to DNA (K b � 10 4 M À 1 ).…”

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

“…Known examples of triazole-based fluorophores have a triazole ring connected to both a donor-type group (EDG, D) and an acceptor-type moiety (EWG, A) ( Figure 1 ). However, the role of triazole as a π-spacer between the electron-donating and electron-withdrawing parts is ambiguous [ 18 , 19 , 20 , 21 , 22 , 23 ]. Thus, the triazole ring includes a lone pair of nitrogens in the conjugation system in the case when the EWG/EDG are attached to the N1/N2 atom and to the C4/C5 atom ( Figure 1 A–E), or it serves as a π-spacer in the case of C4/C5 EWG/EDG-disubstituted triazoles ( Figure 1 F).…”

Sensitive hydrazine detection and quantification with a fluorescent benzothiadiazole sensor: selective lipid droplets andin vivoimaging

“…The limit of detection (LOD) and limit of quantification (LOQ) for the developed sensor were determined using standard procedures [116][117][118] (Fig. S7 †) (see details in the Experimental section).…”