No abstract

We report the synthesis and characterization of two new mesoferrocenylporphyrins, with the ferrocenyl unit attached at the para position of a C 6 F 4 group by a C-N bond with -NH(CH 2 ) 2 NH-(2a) and -NH(CH 2 ) 4 NH-(2b) spacers. Compounds 2a and 2b were characterized through elemental analyses, electrospray ionization high-resolution mass spectrometry, 1 H NMR, UV-visible and fluorescence spectroscopies, electrochemistry and spectroelectrochemistry. The free base porphyrin 2 was included for comparison purposes. The binding ability of 2 and the porphyrin derivatives 2a and 2b with calf thymus DNA was determined using UV-visible and fluorescence spectroscopies. The results suggest that the interaction of these systems most probably occurs through π-stacking by non-classical modes involving the partial insertion of the C 6 F 5 ring between adjacent base pairs on DNA and possible hydrogen interaction with the aliphatic -NH(CH 2 ) n NH-(n = 2 or 4) groups with calf thymus DNA. Moreover, we also demonstrate that porphyrins generate singlet oxygen species and show good photostability after irradiation.

In this work, we evaluate the interaction of the peripheral Pt(bpy)Cl substituted porphyrins, H2PtPor and ZnPtPor with DNA using UV-vis, emission fluorescence, CD spectroscopy, and DNA melting properties altered by the Pt(ii)-porphyrinoid compounds. Additionally, we observe the ability of these porphyrin derivatives to generate O and to efficiently photocleave plasmid DNA upon visible light irradiation based on a mixed (oxidative/hydrolytic) mechanism.

No abstract

We aimed to synthesize a new series of triazacyclononanyl-porphyrins (4 and 5) with the potential ability to bind DNA. For this, the free-base porphyrin 4 and the corresponding Zn(ii)-complex 5 were synthesized by the Schiff base formation reaction. The binding ability of the porphyrin derivatives 4 and 5 with DNA from calf-thymus was studied by UV-vis and emission spectroscopy. Detailed analysis of the results suggests that the interaction of these systems most probably occurs through π-stacking and secondary hydrogen interaction surface binding with ct-DNA. Moreover, we also demonstrate the substantial ability of porphyrins 4 and 5 to generate (1)O2 and to photocleave plasmid DNA after irradiation.

Abstract:The vital function played by porphyrin derivatives in nature has attracted the attention of many scientists for more than a century. Studies on the synthesis, functionalization, action of porphyrins and the search for potential applications of such macrocycles were carried out during the last century, and they have involved several research groups. In this context, the establishment of novel synthetic routes has been a major objective over the years. In this review, the importance of nitro-and aminoporphyrins as templates for the formation of new specifically substituted porphyrins will be presented. Derivatives containing nitro and amino groups are presented as important starting materials for the formation of new highly functionalized porphyrin derivatives.Keywords: Porphyrins; nitro-porphyrins; amino-porphyrins. ResumoAs funções vitais desempenhadas por derivados porfirínicos na natureza tem atraído a atenção de muitos cientistas por mais de um século. Estudos sobre a síntese, funcionalização, e modo de ação de porfirinas e sobre a busca de potenciais aplicações destes macrociclos foram realizadas durante o século passado e envolveram variados grupos de pesquisa. Nesse contexto, o estabelecimento de novas rotas sintéticas tem sido um dos principais objetivos ao longo dos anos. Neste manuscrito será tratada a importância de nitro-e amino-porfirinas como moléculas-chave para a formação de novas porfirinas especificamente substituídas. Derivados contendo grupos nitro e amino são apresentados como importantes materiais de partida para a formação de novos derivados porfirínicos funcionalizados. Palavras-chave:Porfirinas; nitro-porfirinas; amino-porfirinas.