Design,Synthesis And Performance Research Of Fluorescent Molecular Probes Based On BODIPY And BBN

The discovery of lead compounds and herbicide targets is crucial for the development of novel chemical herbicides.It will greatly promote the discovery of new herbicide targets to establish a quick and easy method of target localization.Studies have shown that ?-alkyl-IAAs are a kind of effective auxin inhibitors,which possibly become a kind of novel auxin-type herbicides.Therefore,it is instructive for the creation of auxin-type herbicides to study ?-alkyl-IAAs' targets and role models by fluorescent molecular probes.In this thesis,we designed and synthesized two series of fluorescent compounds including BODIPY(4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene)derivatives and BBN(BF2-rigidified benz[c,d]indole N-heteroarene)derivatives,which were applied to build fluorescent molecular probes that could be further employed to perform relevant studies.The research will help to establish a quick and efficient method of target discovery.The specific work content has four parts:1.Activity-based probes(ABPs)and their research progress were roughly outlined.In addition,characteristics and research progress of BODIPY and other fluorescent dyes were reviewed in detail.Based on this knowledge,project design was put forward finally.2.Two series of fluorescent compounds with carboxyl group were designed and synthesized.On the one hand,with pyrroles and benzaldehydes as raw materials,BODIPYs containing carboxyl group were synthesized.On the other hand,BBNs with carboxyl group were synthesized from 1,8-naphthalene lactam and 6-chloro pyridine-2-amine.Then,the structures of these compounds were confirmed by 'H NMR,13C NMR,FTIR and MS.Subsequently,the optical properties were studied by UV-visible Spectroscopy and Fluorescent Spectroscopy.The results indicated that BODIPY derivatives 3b and 9 possessed excellent features of high fluorescence quantum yield(over 0.7)and long emission wavelength(over 500 nm);BBN derivatives 19a possessed excellent features of high fluorescence quantum yield(0.89)and large Stokes shift(1938 cm-1).3.Two fluorescent molecular probes were designed and synthesized,which consisted of reactive group,linker unit and reporter group.With compound 3b and methyl ?-(6-aminohexyl)-indole-3-acetate as raw materials,probe 23 was synthesized by amidation reaction and hydrolysis reaction.Probe 26 was obtained from compound 9 and methyl ?-(6-aminohexyl)-N-methoxycarbonyl-indole-3-acetate in the same way.Then,the structures of these compounds were confirmed by 1H NMR,13C NMR,FTIR and MS.Subsequently,the optical properties were studied by UV-visible Spectroscopy and Fluorescent Spectroscopy.The results indicated that both fluorescent molecular probes had good spectral properties as same as their parent compounds.4.The biological activity test of two fluorescent molecular probes was conducted.The results showed that both the probes obviously inhabited the growth of Arabidopsis Thaliana's lateral root and root hair.Finally,Arabidopsis Thaliana seedlings were co-cultured with probe 23,and their roots were sequently imaged by fluorescence microscope.The results indicated that the distribution of probe 23 had high specificity,mainly in epidermis cells and cortex cells of Arabidopsis Thaliana's roots.Therefore,it can be concluded that a-(6-aminohexyl)-indole-3-indole acetic acid hydrochloride as a reactive molecule was likely to bind specially with one of protein TIR1 and protein PIN2,or the both.