Photodynamic antimicrobial chemotherapy of asymmetric porphyrin-silver conjugates towards photoinactivation of Staphylococcus aureus

Abstract

Asymmetric mono-carboxy-porphyrins, (5-(4-carboxyphenyl)−10,15,20-tris(pentafluorophenyl)porphyrinato zinc(II) (1), 5-(4-carboxyphenyl)−10,15,20-triphenylporphyrinato zinc(II) (2) and 5-(4-carboxyphenyl)−10,15,20-tris(2-thienyl)porphyrinato zinc(II) (3), were linked to Ag nanoparticles (AgNPs) through amide bonds and self-assembly (the latter only for 3). The porphyrins and conjugates were used for photodynamic antimicrobial chemotherapy (PACT) against Staphylococcus aureus. PACT uses singlet oxygen for antimicrobial activity. Complex 3 and its conjugates had higher singlet oxygen quantum yields and higher log reduction when compared with the rest of the porphyrins and corresponding conjugates. These high log reductions for 3 and its conjugate were attributed to the presence of sulfur groups whereby there was more interaction with the bacterial membrane.

Graphical Abstract

Keywords:

• Silver nanoparticles
• zinc porphyrins
• singlet oxygen quantum yield
• photodynamic antimicrobial chemotherapy

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the Department of Science and Technology (DST)/Nanotechnology (NIC) and National Research Foundation (NRF) of South Africa through DST/NRF South African Research Chairs Initiative for Professor of Medicinal Chemistry and Nanotechnology (UID 62620), Desmond Goddard bursary and Rhodes University.