Photodynamic antimicrobial chemotherapy activities of phthalocyanine-antibiotic conjugates against bacterial biofilms and interactions with extracellular polymeric substances.

This study sheds light on how to rationally design efficient photodynamic antimicrobial chemotherapy (PACT) agents by covalently linking phthalocyanines (Pcs) as photosensitizers with an antibiotic: Ciprofloxacin (CIP). Pcs used are zinc (II) 3-(4-((3,17,23-tris(4-(Benzo(d)thiazol-2-yl] thiol) phthalocyanine-9-yl) oxy) phenyl) propanoic acid (1) and zinc (II) 3-(4-(3,17,23-tris(3-(4-(triphenylphosphine) butyl) benzo[d]thiazol-3-ium bromide phthalocyanine-9-yl) oxy) phenyl) propanoic acid (2). High singlet oxygen quantum yields are observed in the presence of CIP. Square wave voltammetry was used to analyse the Pc-CIP uptake by bacteria biofilms of Streptococcus pneumoniae (S. pneumonia) and Escherichia coli (E. coli). Electrochemical impedance spectroscopy and scanning electron spectroscopy were used to study the stability of the biofilms in the presence Pc-CIP complexes and when exposed to light. Raman and time of flight-secondary ion mass spectrometry (TOF-SIMS) are used to identify the breakdown of cellular components of the biofilm and penetration of the Pc-CIP into the biofilms, respectively.

Evaluation of the antibacterial activity of gallic acid anchored phthalocyanine-doped silica nanoparticles towards Escherichia coli and Staphylococcus aureus biofilms and planktonic cells.

In this work, we have described the synthesis of phthalocyanine complexes Zn(II) tetrakis 4-(5-formylpyridin-2-yl)oxy) phthalocyanine (2), Zn(II) tetrakis-1­butyl­4-(2-(6- (tetra-phenoxy)pyridin-3-yl) vinyl)pyridin-1-ium phthalocyanine (3) and Zn(II) tetrakis 1­butyl­5-(2-(1-butylpyridin-1-ium-4-yl)vinyl)-2-(tetra-phenoxy)pyridin-1-ium phthalocyanine (4). The effect of a varying number of charges when the Pc complexes are alone or grafted in gallic acid (GA) tagged silica nanoparticles on photodynamic antimicrobial chemotherapy (PACT) is investigated toward Staphylococcus aureus (S.aureus) and Escherichia coli (E.coli) in both planktonic and biofilm forms. Complex 4, bearing a total of 8 cationic charges, displayed the highest activity with log CFU (colony forming units) values of 8.60 and 6.42 against E.coli and S.aureus biofilms, respectively. The surface stability of E.coli and S.aureus biofilms in the presence of 4 and its conjugate was analyzed using cyclic voltammetry. Scanning electron microscopy (SEM) and Raman spectra are also used to study the conformational and biochemical changes within biofilm upon subjecting them to PACT.