Synthesis and Discovery of Schiff Base Bearing Furopyrimidinone for Selective Recognition of Zn2+ and its Applications in Cell Imaging and Detection of Cu2.

Yanggen Hu,Juncai Fu,Lili Gui,Xinya Han,Junkai Ma,Jing Lu,Chao Luo,Lun Luo

doi:10.3389/fchem.2021.774090

Abstract

A simplefuro [2,3-d]pyrimidinone-based Schiff base FPS was synthesized via aza-Wittig reaction and structure elucidation was carried out by spectroscopic studies FT-IR, 1H NMR, and 13C NMR and mass spectrometry. FPS showed weak fluorescence emission in methanol and the selectivity of FPS to different metal ions (Mn2+, Ca2+, Fe2+, Fe3+, Mg2+, Al3+, Ba2+, Ag+, Co2+, Na+, K+, Cu2+, Zn2+, Pb2+, Bi3+) were studied by absorption and fluorescence titration. The results show that FPS has selective fluorescence sensing behavior for Zn2+ ions and the limit of detection (LOD) was calculated to be 1.19 × 10–8 mol/L. Moreover, FPS-Zn2+ acts as a metal based highly selective and sensitive new chemosensor for Cu2+ ions and the LOD was calculated to be 2.25 × 10–7 mol/L. In accordance with the results and theoretical calculations, we suspected that the binding mechanisms of FPS to Zn2+ and Cu2+ were assigned to be the cooperative interaction of Zn2+(Cu2+)-N.

Highlights

Metal ions have pivotal functions for the growth and development process of organisms, and it is of great significance to identify and monitor metal ions in the environment and in organisms (Domingo 1994; Schmidt et al, 2009; Garza-Lombo et al, 2018)
We designed a Schiff base bearing furopyrimidinone scaffold (FPS) synthesized from 2hydroxy-benzaldehyde with furo [2,3-d]-pyrimidine-5carbohydrazide (Scheme 1), and fluorescence analysis showed that FPS displayed highly selective recognition Zn2+ with no apparent interference from other metal ions in MeOH solution and its applications in cell imaging and detection Cu2+ ions
Synthesis of N’-(2-hydroxybenzylidene)-3,4-dihydro6-methyl-4-Oxo-2-(propylamino)-3-P-tolylfuro[2,3-d] pyrimidine-5-carbohydrazide FPS A mixture of 3 (1.1 g, 3 mmol) and salicylaldehyde (3 mmol) in 25 ml ethanol was stirred for 10 h at 70–75°C, after the solution was concentrated under reduced pressure and the solid was collected and recrystallized from CH2Cl2/EtOH to give FPS (1.1 g, 84%). m. p.: 216–218°C. 1H NMR (400 MHz, DMSOd6): δ 13.55, 8.35 (s, 1H, N CH), 7.58–6.89 (m, 8H, Ar-H), 6.51, 3.23 (q, J 8.0, 2H, CH2), 2.72 (s, 3H, CH3), 2.45 (s, 3H, CH3), 0.82 (t, J 8.0, 3H, CH3). 13C NMR (100 MHz, DMSO-d6): δ 11.1, 13.3, 20.9, 21.6, 43.1, 92.6, 109.8, 116.3, 118.6, 119.3, 128.8, 129.7, 131.0, 131.4, 131.5, 139.3, 147.4, 152.9, 155.2, 157.4, 158.0, 160.7, 165.1

Summary

INTRODUCTION

Metal ions have pivotal functions for the growth and development process of organisms, and it is of great significance to identify and monitor metal ions in the environment and in organisms (Domingo 1994; Schmidt et al, 2009; Garza-Lombo et al, 2018). In the past few years, many researchers have been devoted to finding and developing of some site-specific small-molecule fluorescence probes for highly selective recognition of metal ions (Liang et al, 2017; Bae et al, 2018; Yang et al, 2019) and for analyzing different metal ions, which are widely distributed in organisms and environments worldwide (Wang et al, 2019; Kim et al, 2021; Klenner et al, 2021; Sannigrahi et al, 2021). Synthesis of N’-(2-hydroxybenzylidene)-3,4-dihydro6-methyl-4-Oxo-2-(propylamino)-3-P-tolylfuro[2,3-d] pyrimidine-5-carbohydrazide FPS A mixture of 3 (1.1 g, 3 mmol) and salicylaldehyde (3 mmol) in 25 ml ethanol was stirred for 10 h at 70–75°C, after the solution was concentrated under reduced pressure and the solid was collected and recrystallized from CH2Cl2/EtOH to give FPS (1.1 g, 84%). Showed that FPS exhibited low cytotoxicity against Hela cell lines with IC50 more than 500 μmol/L

AND DISCUSSION

DATA AVAILABILITY STATEMENT

Findings

CONCLUSION