Enhanced photo-ablation effect of positively charged phthalocyanines-detonation nanodiamonds nanoplatforms for the suppression of Staphylococcus aureus and Escherichia coli planktonic cells and biofilms

Photodynamic antimicrobial therapy (PACT) is a powerful technic recommended to eliminate life-threatening pathogens that cause localized and superficial infections as pathogens cannot develop resistance to it. For this reason, new positively charged chalcone substituted zinc (3a) and indium (4a) metalated phthalocyanines (Pcs) were synthesized and were π-π interacted with detonation nanodiamonds (DNDs) nanoparticles to form new water soluble nanoplatfoms 3a@DNDs and 4a@DNDs. The conjugates generated high singlet oxygen quantum yields (ΦΔ) in water (1% DMSO, used for PACT studies) with values of 0.46 and 0.47 for 3a@DNDs and 4a@DNDs, respectively. Hence, they were tested for PACT against biofilms of S. aureus and E. coli, as well as their planktonic cells. The quaternized Pcs alone 3a and 4a as well as their nanoconjugates 3a@DNDs and 4a@DNDs were effective PACT agents with log10 CFU > 9 for E. coli and S. aureus. The quaternized derivatives were found to have higher ability to completely suppress both planktonic and biofilms of S. aureus and E. coli in vitro. Therefore, they could be used as appropriate photosensitive agents

Photodynamic antimicrobial action of asymmetrical porphyrins functionalized silver-detonation nanodiamonds nanoplatforms for the suppression of Staphylococcus aureus planktonic cells and biofilms

New asymmetrical porphyrin derivatives containing a p-hydroxyphenyl moiety and p-acetylphenyl moieties along with their functionalized silver-detonation nanodiamonds nanohybrids were characterized and their photophysicochemical properties were established. The study provides evidence that the metalated porphyrin derivatives were red-shifted in absorption wavelength and possessed high singlet oxygen quantum yield comparative to the unmetalated core, thus making them suitable agents for photodynamic antimicrobial chemotherapy. As a result of conjugation to detonation nanodiamonds and silver nanoparticles, these compounds proved to be more effective as they exhibited stronger antibacterial and anti-biofilm activities on the multi-drug resistant S. aureus strain due to synergetic effect, compared to Ps alone. This suggests that the newly prepared nanohybrids could be used as a potential antimicrobial agent in the treatment of biofilms caused by S. aureus strain

Acetophenone substituted phthalocyanines and their graphene quantum dots conjugates as photosensitizers for photodynamic antimicrobial chemotherapy against Staphylococcus aureus

This work reports on the synthesis and characterization of novel acetophenone substituted phthalocyanines along with the self-assembled nanoconjugates formed via π-π stacking interaction between the synthesized unmetalated (2), zinc (3) and indium (4) phthalocyanines and graphene quantum dots (GQDs) to form 2@GQDs, 3@GQDs and 4@GQDs. The complexes and conjugates exhibited high singlet oxygen ranging from 0.20 to 0.79 in DMSO for Pcs and nanoconjugates where in all cases, the indium complexes showed the highest singlet oxygen quantum yields. The photodynamic antimicrobial chemotherapy activity of both phthalocyanines and nanoconjugates were tested against Staphylococcus aureus. 4@GQDs was found to be highly effective causing a 9.68 log reduction of the bacteria at 10 μM (based on Pc) when compared to 3.77 log reduction of 3@GQDs

Synthesis, theoretical calculations and laser flash photolysis studies of selected amphiphilic porphyrin derivatives used as biofilm photodegradative materials

Photodynamic antimicrobial activities of gallium and indium porphyrins as well as their quaternized derivatives have been investigated against S. aureus and E. coli biofilms, as well as on their planktonic (free floating) cells using a light emitting diode lamp at 415 nm. The studied photosensitizers show considerable ability to generate singlet oxygen and the quaternized molecules 2a and 3a are potential photodynamic antimicrobial chemotherapy (PACT) agents with log10 colony forming units >9 for E. coli and S. aureus planktonic cells. The quaternized derivatives are found to have higher ability to significantly suppress the biofilms of both S. aureus and E. coli in vitro. Therefore, this demonstrates that they are potentially suitable photosensitive agents for PACT use. The TD-B3LYP/LanL2DZ calculations were performed to evaluate the singlet excitation energies of quaternized and non-quaternized porphyrins in vacuo. Our study shows excellent agreement between time-dependent density-functional theory (TD-DFT) excited energies and experimental S1 > S0 excitation energies. The small deviation observed between the calculated and experimental spectra arises from the solvent effect. The excitation energies observed in these UV-visible spectra mostly originated from electron promotion between the highest occupied molecular orbital (HOMO) for the less intense band and the HOMO−1 for the most intense band of the ground states to the lower unoccupied molecular orbital (LUMO) of the excited states

Detonation nanodiamonds-phthalocyanine photosensitizers with enhanced photophysicochemical properties and effective photoantibacterial activity

The nanophotosensitizers based on acetophenoxy tetrasubstituted metallophthalocyanines (MPc) and detonation nanodiamonds (DNDs) were successfully formed and their photophysicochemical properties were determined. The zinc(II)Pc and indium(III)Pc complexes along with their nanoconjugates were found to have high singlet oxygen quantum yields (0.72 − 0.84) associated with the heavy central metal effect. The ability of the functional groups present on the DNDs to bind to the bacteria cell and the improved solubility of the nanoconjugates due to DNDs resulted in effective photodynamic antimicrobial therapy (PACT) activity against S. aureus planktonic cells, with the highest log reduction of 9.72 ± 0.02 for the conjugate of InPc conjugate with DNDs after 30 min irradiation. PACT studies were investigated at a dose of 10 μg/mL for each sample. The results suggest that the readily synthesized nanoconjugates can be used as appropriate PACT agents