Synthesis and antimicrobial activity of meso-substituted polymethine cyanine dyes

El-Aal, Reda M. Abd; Younis, Magdi

doi:10.1016/j.bioorg.2004.04.001

Cited by 11 publications

(9 citation statements)

References 22 publications

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“…Additionally, there is an interesting study showing the effects of 12 cyanine-derived synthesized compounds upon inactivation of Gram-positive and Gram-negative bacteria, yeast, and fungi. Among these compounds, four were actually superior at killing Gram-negative cells, and this was attributed to their chemical structure comprising naphthol and cyano groups and pyrazole heterocyclic rings [106]. …”

Section: Nonporphyrin-based Photosensitizersmentioning

confidence: 99%

Antimicrobial Photodynamic Therapy to Kill Gram-negative Bacteria

Sperandio¹,

Huang²,

Hamblin³

2013

PRI

467

283

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Antimicrobial photodynamic therapy (PDT) or photodynamic inactivation (PDI) is a new promising strategy to eradicate pathogenic microorganisms such as Gram-positive and Gram-negative bacteria, yeasts and fungi. The search for new approaches that can kill bacteria but do not induce the appearance of undesired drug-resistant strains suggests that PDT may have advantages over traditional antibiotic therapy. PDT is a non-thermal photochemical reaction that involves the simultaneous presence of visible light, oxygen and a dye or photosensitizer (PS). Several PS have been studied for their ability to bind to bacteria and efficiently generate reactive oxygen species (ROS) upon photostimulation. ROS are formed through type I or II mechanisms and may inactivate several classes of microbial cells including Gram-negative bacteria such as Pseudomonas aeruginosa, which are typically characterized by an impermeable outer cell membrane that contains endotoxins and blocks antibiotics, dyes, and detergents, protecting the sensitive inner membrane and cell wall. This review covers significant peer-reviewed articles together with US and World patents that were filed within the past few years and that relate to the eradication of Gram-negative bacteria via PDI or PDT. It is organized mainly according to the nature of the PS involved and includes natural or synthetic food dyes; cationic dyes such as methylene blue and toluidine blue; tetrapyrrole derivatives such as phthalocyanines, chlorins, porphyrins, chlorophyll and bacteriochlorophyll derivatives; functionalized fullerenes; nanoparticles combined with different PS; other formulations designed to target PS to bacteria; photoactive materials and surfaces; conjugates between PS and polycationic polymers or antibodies; and permeabilizing agents such as EDTA, PMNP and CaCl2. The present review also covers the different laboratory animal models normally used to treat Gram-negative bacterial infections with antimicrobial PDT.

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Section: Nonporphyrin-based Photosensitizersmentioning

confidence: 99%

Antimicrobial Photodynamic Therapy to Kill Gram-negative Bacteria

Sperandio¹,

Huang²,

Hamblin³

2013

PRI

467

283

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“…The meso position substitution of the heptamethine fluorophores has continuously been investigated, 21,22 and it is well known that their essential optical properties including absorption and emission wavelengths, Stokes shift, extinction coefficient, quantum yield, and photostability are directly influenced by the substitution at this position. Therefore, we also performed optical and chemical stability of C-C coupled heptamethine fluorophores in vitro as well as their biodistribution and clearance in small and large animals.…”

mentioning

confidence: 99%

Central C–C bonding increases optical and chemical stability of NIR fluorophores

et al. 2014

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Functional near-infrared (NIR) fluorophores have played a major role in the recent advances in bioimaging. However, the optical and physicochemical stabilities of NIR fluorophores in the biological and physiological environment are still a challenge. Especially, the ether linkage on the meso carbon of heptamethine core is fragile when exposed to serum proteins or other amine-rich biomolecules. To solve such a structural limitation, a rigid carbon-carbon bond was installed onto the framework of ether-linked NIR fluorophores through the Suzuki coupling. The robust fluorophores replaced as ZW800-1C and ZW800-3C displayed enhanced optical and chemical stability in various solvents and a 100% warm serum environment (> 99%, 24 h). The biodistribution and clearance of C-C coupled ZW800 compounds were almost identical to the previously developed oxygen-substituted ZW800 compounds. When conjugated with a small molecule ligand, ZW800-1C maintained the identical stable form in warm serum (>98%, 24 h), while ZW800-1A hydrolyzed quickly after 4 h incubation (34%, 24 h).

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“…In continuation of our interest by cyanine dyes, several types of cyanines by different routes have been synthsised [19][20][21][22][23][24]. Here, by using a joint theoretical and experimental approach, we demonstrate the correspondence between cyanines and the new class of cyanine-like dyes involving heterocyclic quinone of benzo[g]quinoline derivatives [25,26].…”

Section: Introductionmentioning

confidence: 94%