Synthesis Of Azobenzene Compounds With Visible Light Response And Study On Their Interaction With BSA

Azobenzene compounds are photochromic substances containing double bonds of nitrogen and nitrogen.Under the action of visible light,the photochromic compounds will change configuration and then produce discoloration effect.Because of their photoresponse properties,these compounds are mainly used in molecular probes,molecular switches and dye dyeing.They can also be used in many fields such as drug release,optical information storage,liquid crystal materials and so on in biomedicine.In a word,azobenzene compounds have a good application prospect for a long time.In recent years,the use of visible light to regulate azobenzene drug delivery system,that is,the occurrence of light-induced reactions to release drugs for biological specific targets.So that drugs can be more effective in target organs or target cells,after the action was completed,the reaction of light-induced to reduce the drug toxicity and improve the efficacy of treatment.The application of azobenzene in this field has attracted extensive interests.We know that ultraviolet light can cause the response of azobenzene substances and can be used in drug delivery in organisms.However,ultraviolet light has poor penetration and great harm to tissues of organisms.With compared to ultraviolet light,the visible light contained in infrared light and the near-infrared wavelength light,which can circumvent these disadvantages,and are more suitable for biomedical applications.Therefore,it is necessary to synthesize azo-type compounds of visible light response and to study their effects on biomass.Firstly,a series of azobenzene compounds were synthesized by the reaction of3,5-dimethyl phenol with 2,6-dimethyl aniline,2,6-diethyl aniline and 2,6-diisopropyl aniline under nitrogen condition.[?2,6-Me₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OH]?1?,[?2,6-Et₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OH]?2?,[?2,6-i-Pr₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OH]?3?,these three compounds were characterized by IR,1H NMR and so on.Secondly,the three compounds were further reacted with 1,2-dibromoethane,1,6-dibromohexane,1,8-dibromooctane and 1,10-dibromodecane respectively to obtain the compound:[?2,6-Me₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₂H₄Br]?1a?,[?2,6-Me₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₆H₁₂Br]?1b?,[?2,6-Me₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₈H₁₆Br]?1c?,[?2,6-Me₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₁₀H₂₀Br]?1d?,[?2,6-Et₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₂H₄Br]?2a?,[?2,6-Et₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₆H₁₂Br]?2b?,[?2,6-Et₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₈H₁₆Br]?2c?,[?2,6-Et₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₁₀H₂₀Br]?2d?,[?2,6-i-Pr₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₂H₄Br]?3a?,[?2,6-i-Pr₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₆H₁₂Br]?3b?,[?2,6-i-Pr₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₈H₁₆Br]?3c?,[?2,6-i-Pr₂?C₆H₃N=NC₆H₂?3,5-Me₂?-OC₁₀H₂₀Br]?3d?,the above 12 compounds were characterized by IR,UV and 1H NMR.Finally,according to the changes of UV spectra for compounds 1-3 and 1a-1d,2a-2d,3a-3d after irradiation with different wavelengths of light,we compared and analyzed the responses of the compounds to blue-purple,green and red light after exposure to different wavelengths of light,and compared and analyzed the response of the compounds to blue-purple,green and red light after illumination.It can be seen that substances 1,1c,2c,3b respond better to blue-violet light,green light and red light,and the compounds substituted by methyl are more responsive to visible light than those with ethyl and isopropyl groups.Compound 1,2,3 is solid at room temperature,1a?2 alkyl chains?,1b?6 alkyl chains?,1c?8 alkyl chains?at room temperature,and 1d?10 alkyl chains?as liquid at room temperature when the ortho-positions are substituted by methyl.It can be seen that different chain lengths have an effect on the physical state of the compounds?2a-2d,3a-3d are not discussed in liquid matter at room temperature?.During the experiment,we found that 1,1a-1c are all solid compounds,and the compounds synthesized from 1 are better than the compounds synthesized by 2,3,and the photoresponse of the compounds synthesized by 1 is better than that of the compounds synthesized by 2,3.Then,the effects of azobenzene compounds 1,1a-1c on the protein-protein interaction were studied by quantitative method.One,after the interaction of the interaction of visible light with different wavelengths,it can be seen that the UV spectrum curve is obviously reduced,which means that the compound is added after the compound is added into the BSA,and the compound has a certain influence on the peptide chain of the BSA.Secondly,the change of fluorescence spectrum after the interaction of compounds 1,1a-1c with BSA is studied.It can be seen that the fluorescence of BSA is quenched,and the blue shift of wavelength is obvious,which indicates that the structure of BSA has changed.