Bis-triazole linked organosilane based sensing platform for Cu2+ ions and insilico tyrosinase inhibitor activity

Abstract

The development of a ligand for their selective and sensitive detection is required due to the widespread use of Cu2+ in many industrial processes and the potential threat to human health. Herein, we report a bis-triazole linked organosilane (5) derived from the Cu(I) catalyzed azide-alkyne cycloaddition reaction. The synthesized compound 5 was characterized by (1H and 13C) NMR spectroscopic and mass spectrometry techniques. The UV–Visible and Fluorescence experiments of the designed compound 5 were performed with various metal ions, revealing its high selectivity and sensitivity to Cu2+ ions in MeOH: H2O (8:2, v/v, pH = 7.0, PBS buffer) solution. The selective fluorescence quenching upon addition of Cu2+ to the compound 5 is due to Photo-induced electron transfer process (PET). The limit of detection of compound 5 to Cu2+ was calculated as 2.56 × 10−6 M and 4.36 × 10−7 M through UV–Visible and Fluorescence titration data, respectively. The possible mechanism of 1:1 binding of 5 with Cu2+ could be affirmed by the density functional theory (DFT). Further, it was found that compound 5 showed a reversible behavior towards Cu2+ ions by the accumulation of sodium salt of CH3COO– which can be used in the construction of molecular logic gate where Cu2+ and CH3COO– are considered as inputs and the absorbance at 260 nm as output. Moreover, the molecular docking studies provide useful information about compound 5′s interaction with the tyrosinase enzyme (PDB ID- 2Y9X).