The Synthesis And Characterization Of Singlet Oxygen Production Ability Of Porphyrin Derivatives

Porphyrin-based photosensitizers have very important theoretical and practical value in photodynamic therapy(PDT)for the treatment of cancers.On this basis,a series of porphyrin derivatives were designed and synthesized firstly,and a push-pull porphyrin-based photosensitizer was finally constructed in this paper.Its chemical structure was characterized by nuclear magnetic resonance,mass spectrum,melting point and infrared ray,and its ultraviolet-visible absorption spectrum and singlet oxygen production capacity were analyzed.Then,inspired by bionics,artificial chloroplasts(porphyrins were integrated on the surface of gold nanoparticles to construct complex energy bodies with synergistic effect)were constructed to expand and supplement the light absorption capacity of materials.Finally,it was applied to construct functional colloidal particles,i.e.,safe and non-toxic capsules were used to coat the porphyrin compounds and their release behavior was detected,which lays a foundation for further practical application.In this paper,a total of 4 porphyrin derivatives were synthesized successfully,5,15-bis[3-(1-bromopentanoxy)-4-bromohexadecanoxybenzaldehyde]porphyrin(SYK-10),5,15-bis[3-(1-bromopentanyloxy)-4-bromohexadecanoxybenzaldehyde]-10,20-dibromozinc porphyrin(SYK-11),5,15-bis[3-(pentanoxythioacetate)-4-bromohexadecanoxybenzaldehyde]zinc porphyrin(SYK-12)and 5,15-bis[3-(pentanoxythioacetate)-4-bromohexadecanoxybenzaldehyde]-10,20-bis(2-alkynylanthraquinone)zinc porphyrin(SYK-17),respectively.The effects of porphyrin structure on molar absorption coefficient and absorption band were investigated by analyzing its ultraviolet-visible absorption spectrum.Xanthan gum capsules were successfully prepared,and it was found that these capsules could be used for encapsulation and release of porphyrin compounds as transporters.The ability of these porphyrin compounds to produce singlet oxygen was detected.It was revealed that the 4 synthesized porphyrin compounds showed the ability to produce singlet oxygen under long-wavelength(590 nm)light.the 4 synthesized porphyrin compounds in this paper can be used as novel organic photosensitive elements in the photosensitizer family and are expected to be used in the next photodynamic therapy.