Synthesis And Properties Of Nucleoside Analogs Modified By Fluorophore

With the gradually development of fluorescence technology,fluorescent nucleotide analogue have been applied extensively in the fields of biochemistry and medicinal chemistry,due to their high sensitivity,good selectivity,low interference,easy design,reproducible synthesis,and high stability.Fluorescent nucleoside analogues modified by fluorophore can significantly improve the photophysical properties to present excellent environmental sensitivity,brings the application prospect of fluorescent probe and bioimaging.In this thesis,two types of fluorescent nucleotide analogue have been achieved through modified by fluorophore and investigated about the fluorescent properties,characterized by ¹HNMR,¹³CNMR,and MS,and absorption and emission spectroscopy.Firstly,two fluorescent nucleotide analogue 7a and 6b modified by diketopyrrolopyrrole（DPP）were synthesized and explores the fluorescent properties.Modified by DPP through a seven-step or six-step reaction route respectively,two fluorescent nucleoside analogs connected by an ethynyl or have been obtained.The investigation about fluorescent nucleoside analogs connected by an ethynyl indicate that the fluorescent nucleoside analogs rigidly connected by DPP show a maximum absorption and emission peak in 485 nm and 555 nm respectively,with the quantum yield of 0.86 in acetonitrile,as an fluorescent probe for environmentally sensitivity.Connected by an ethynyl methoxyl,the fluorescent nucleoside analogs modified flexibly by DPP present the good environmentally sensitivity and the maximum absorption peak in and 474nm,with the maximum emission in 534 nm and the quantum yield of 0.88 in acetonitrile.Secondly,the fluorescent nucleotide analogue modified by fluorescein was obtained.Synthesized through a three-step reaction route,the fluorescent nucleoside analog modified with 2,7-dichlorofluorescein show the quantum yield of 0.81,with the maximum absorption and the maximum emission peak in 461 nm and 540 nm respectively.In study in polarity,p H,and viscosity,the fluorescent nucleotide analogue suggest good environmentally sensitivity as a potential fluorescent probe,particularly the increaseing dramatically fluorescence intensity with polarity.Generaly,there fluorescent nucleotide analogue modified by fluorophore have been achieved to promote understanding fluorescent nucleotide analogue for the potential application of fluorescent probes and bioimaging.