Electrostatic binding of substituted metal phthalocyanines to enterobacterial cells: its role in photodynamic inactivation.

Abstract

The effect of ionic substituents in zinc and aluminum phthalocyanine molecules and of membrane surface charge on the interaction of dyes with artificial membranes and enterobacterial cells, as well as on photosensitization efficiency was studied. It has been shown that increasing the number of positively charged substituents enhances the extent of phthalocyanine binding to Escherichia coli cells. This, along with the high quantum yield of singlet oxygen generation, determines efficient photodynamic inactivation of Gram-negative bacteria by zinc and aluminum octacationic phthalocyanines. The effect of Ca2+ and Mg2+ cations and pH on photodynamic inactivation of enterobacteria in the presence of octacationic zinc phthalocyanine has been studied. It has been shown that effects resulting in lowering negative charge on outer membrane protect bacteria against photoinactivation, which confirms the crucial role in this process of the electrostatic interaction of the photosensitizer with the cell wall. Electrostatic nature of binding is consistent with mainly electrostatic character of dye interactions with artificial membranes of different composition. Lower sensitivity of Proteus mirabilis to photodynamic inactivation, compared to that of E. coli and Salmonella enteritidis, due to low affinity of the cationic dye to the cells of this species, was found.

• Authors: M G Strakhovskaya, Y N Antonenko, A A Pashkovskaya, E A Kotova, V Kireev, V G Zhukhovitsky, N A Kuznetsova, O A Yuzhakova, V M Negrimovsky, A B Rubin
• Journal: Biochemistry. Biokhimiia (Biochemistry (Mosc)) Vol. 74 Issue 12 Pg. 1305-14 (Dec 2009) ISSN: 1608-3040 [Electronic] United States
• PMID: 19961410 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Cations
• Fluorescent Dyes
• Indoles
• Isoindoles
• Organometallic Compounds
• Photosensitizing Agents
• Zinc Compounds
• Zn(II)-phthalocyanine
• Singlet Oxygen
• aluminum phthalocyanine
• phthalocyanine

Topics

• Cations (chemistry)
• Enterobacteriaceae (drug effects, metabolism)
• Escherichia coli (drug effects, metabolism)
• Fluorescent Dyes (chemistry, pharmacology)
• Hydrogen-Ion Concentration
• Indoles (chemistry, pharmacology)
• Isoindoles
• Organometallic Compounds (chemistry, pharmacology)
• Photosensitizing Agents (chemistry, pharmacology)
• Singlet Oxygen (metabolism)
• Static Electricity
• Zinc Compounds