Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., Bl. 9, 1113, Sofia, Bulgaria.
Photochem Photobiol Sci. 2011 Jan;10(1):91-102. doi: 10.1039/b9pp00154a. Epub 2010 Oct 29.
Visible light-absorbing cationic water-soluble gallium(III) phthalocyanines (GaPcs) peripherally substituted with four and eight methylpyridyloxy groups were synthesized and investigated as antimicrobial photodynamic sensitizers. The inserted large gallium ion in the phthalocyanine ligand is axially substituted by one hydroxyl group which prevents aggregation of the complexes in aqueous solution. The cellular uptake and the photodynamic activity for the representative strains of the Gram positive bacteria methicillin-resistant Staphylococcus aureus(MRSA) and Enterococcus faecalis, of the Gram negative bacterium Pseudomonas aeruginosa and of the fungus Candida albicans in planktonic phase were studied. The tetra-methylpyridyloxy substituted GaPc1 showed lower cellular uptake compared to the octa-methylpyridyloxy substituted GaPc2. The photodynamic activity of the GaPcs was studied in comparison to methylene blue (MB) and a photodynamically active Zn(II)-phthalocyanine with the same substitution (ZnPcMe). Photodynamic treatment with 3.0 μM GaPc1 at mild light conditions (50 J cm(-2), 60 mW cm(-2)) resulted in a high photoinactivation of the microorganisms in the planktonic phase nevertheless the dark toxicity of GaPc1 towards MRSA and E. faecalis. GaPcs against fungal biofilm grown on polymethylmethacrylate (PMMC) resin showed a complete inactivation at a higher concentration of GaPc2 (6.0 μM) and of the referent sensitizer ZnPcMe. However, the bacterial biofilms were not susceptible to treatment of GaPcs with only 1-2 log reduction of the biofilm. The bacterial biofilm E. faecalis was effectively inactivated only with MB. The water-soluble octa-methylpyridyloxy substituted GaPc2 has a potential value for photodynamic treatment of C. albicans biofilms formed on denture acrylic resin.
可见光吸收的阳离子水溶性镓（III）酞菁（GaPcs），其外围取代有四个和八个甲基吡啶氧基，被合成并作为抗菌光动力敏化剂进行了研究。酞菁配体中的插入大镓离子轴向被一个羟基取代，这防止了复合物在水溶液中的聚集。对革兰氏阳性菌耐甲氧西林金黄色葡萄球菌（MRSA）和粪肠球菌、革兰氏阴性菌铜绿假单胞菌和浮游生物期真菌白色念珠菌的代表性菌株的细胞摄取和光动力活性进行了研究。与八甲基吡啶氧基取代的 GaPc2 相比，四甲基吡啶氧基取代的 GaPc1 显示出较低的细胞摄取。与亚甲蓝（MB）和具有相同取代基的光动力活性的 Zn（II）-酞菁（ZnPcMe）相比，研究了 GaPcs 的光动力活性。在温和光照条件（50 J cm(-2)，60 mW cm(-2)）下用 3.0 μM GaPc1 进行光动力处理导致浮游生物期微生物的高光灭活，尽管 GaPc1 对 MRSA 和 E. faecalis 的暗毒性。GaPcs 对聚甲基 methacrylate（PMMC）树脂上生长的真菌生物膜显示出在较高浓度的 GaPc2（6.0 μM）和参考敏化剂 ZnPcMe 下完全失活。然而，细菌生物膜对 GaPcs 的处理不敏感，只有 1-2 个对数减少生物膜。只有 MB 才能有效灭活细菌生物膜粪肠球菌。水溶性八甲基吡啶氧基取代的 GaPc2 对义齿丙烯酸树脂上形成的白色念珠菌生物膜的光动力治疗具有潜在价值。
