Design, Synthesis And Performance Study Of Three New Fluorescent Probes For Formaldehyde Detection

Formaldehyde(FA)plays an important role in life activities.It is not only involved in the regulation of gene expression,but also related to the storage and reproduction of long-term memory.However,excessive formaldehyde will pollute the environment and affect people’s health.Therefore,it is urgent to develop a simple and efficient method to detect formaldehyde.In recent years,fluorescent probes have been widely used in biology、chemistry、medicine and other fields due to their advantages of simple operation,simple structure,high selectivity,good sensitivity,and good cell membrane permeability.Many fluorescent probes have been designed and synthesized to detect formaldehyde successfully.These probes have different structures,reaction mechanism with formaldehyde,response time,sensitivity,selectivity and so on.At present,the development of formaldehyde fluorescent probe with rapid response,good sensitivity,high selectivity and low toxicity is still a research subject of great concern.In this paper,three new formaldehyde fluorescent probes were designed and synthesized,and their properties were investigated.1.A novel formaldehyde fluorescent probe(DFK)was designed and synthesized with isoflurone as parent and hydrazine group as recognition site.It was found that the detection limit of the probe DFK for formaldehyde was low(0.19μM).The fluorescence intensity showed a good linear relationship with the concentration of formaldehyde in the range of 0-80μΜ(Y=1.03311X+0.01928,R~2=0.99788),which could achieve the purpose of quantitative detection of formaldehyde.The probe showed good selectivity and sensitivity to formaldehyde.The probe DFK had low cytotoxicity,and it can be used as a fluorescent probe to detect intracellular formaldehyde.2.Using 1,8-naphthalimide as fluorescence group and hydrazine group as recognition group,a novel fluorescent probe(NID)for formaldehyde detection was designed and synthesized.The synthetic procedure of probe NID was simple and the raw materials was cheap.The results showed that the probe NID had a rapid response to formaldehyde(less than 20 min),low detection limit(0.29μΜ),good selectivity,high sensitivity.And the response of the probe NID to formaldehyde could be recognized by the change of solution color through the naked eye.There was a linear relationship between the fluorescence intensity and the formaldehyde concentration in the range of0-100μM(Y=0.01961X+0.01064,R~2=0.99775).The results of MCF-7 cell imaging experiment showed that the probe could be used as a fluorescent probe to detect intracellular formaldehyde.3.A novel fluorescent probe BZT was constructed by using benzothiazole as the fluorescent group and hydrazine group as the specific reactive group for recognizing formaldehyde.The synthesis method of probe BZT was simple and the reaction conditions were mild.The results showed that the fluorescence intensity of probe BZT showed a good linear relationship with the concentration of formaldehyde in the range of 0-50μM(Y=-0.01116X+0.88161,R~2=0.99121).The probe BZT had characteristics of low detection limit(0.20μM),good selectivity and high sensitivity to formaldehyde,and can also identify the response of the probe to formaldehyde with the naked eye.The probe BZT had low cytotoxicity and can be used as a fluorescent probe to detect intracellular formaldehyde.More importantly,the probe BZT had good biocompatibility and had been applied to the detection of exogenous formaldehyde in zebrafish.