Studies on the synthesis, structural elucidation, and biological evaluation of new conjugates of poly-S-lysine with meso-substituted porphyrins are described. The new conjugates were used in the photoinactivation of antibiotic-resistant Gram-positive bacteria (Staphylococcus aureus strains ATCC 25923 and MRSA 110) and Gram-negative bacteria (Escherichia coli strain O4). The results show that the cationic conjugates are able to photosensitize the efficient inactivation of both types of bacteria.

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The applicability of a novel procedure for the disinfection of microbiologically polluted waters from fish-farming ponds, based on the combined action of visible light (including sunlight) and porphyrin-type photosensitising agents, has been investigated using (a) cell cultures of a Gram-positive bacterium (meticillin-resistant Staphylococcus aureus), a Gram-negative bacterium (Escherichia coli) and a fungal pathogen (Saprolegnia spp.); (b) pilot aquaculture plants involving either spontaneously or artificially Saprolegnia-infected rainbow trout (Oncorhynchus mykiss). The results obtained by using two cationic porphyrins, namely a tetra-substituted N-methyl-pyridyl-porphine (C1) and its analogue where one N-methyl group had been replaced by a N-tetradecyl chain (C14), and low intensity visible light irradiation showed an extensive (up to 6-7 log) decrease in the bacterial/fungal population after short incubation and irradiation times in the presence of micromolar photosensitiser concentrations. Moreover, C14 showed some toxic effect also in the absence of light. Extension of these studies to the pilot plants indicated that both C1 + light and C14 can prevent Saprolegnia infections or promote the cure of saprolegniasis in infected trout by treatments with submicromolar porphyrin doses. The procedure appears to be of low cost and to have a low environmental impact.

Porphyrins have been shown to act as very efficient photosensitizing agents against a broad number of microbial pathogens, including bacteria, fungi, and protozoa. This property has promising applications at a clinical level for the treatment of infectious diseases by photodynamic therapy. Moreover, this technique is also being used to address environmental problems of high significance, such as the decontamination of wastewaters, the disinfection of fish-farming tanks, the protection of animal species (e.g., amphibians and reptiles) that are endangered by pathogens whose life cycle takes place largely in aqueous media, and the control of populations of noxious insects. Such diversified applications take advantage of the availability of a truly large number of porphyrin derivatives with chemical structures that can be tailored to comply with the physical and chemical properties as well as the biological features of several milieus. In addition, the property typical of porphyrins to absorb essentially all of the wavelengths in the sun emission spectrum allows the promotion of processes largely based on natural resources with significant energy savings and low impact on ecosystems.

BackgroundControl of the mosquito vector population is the most effective strategy currently available for the prevention of dengue fever and the containment of outbreaks. Photo-activated oxidants may represent promising tools for developing effective, safe and ecofriendly novel larvicides. The purpose of this study was to evaluate the potential of the synthetic meso-substituted porphyrin meso-tri(N-methylpyridyl), meso-mono(N-tetradecylpyridyl)porphine (C14) as a photoactivatable larvicide against the dengue vector Aedes (Stegomyia) aegypti.MethodologyThe photophysical and photochemical properties of the C14 molecule were assessed spectrophotometrically. Photomediated larvicidal efficacy, route of intake and site of action were determined on Ae. aegypti larvae by laboratory bioassays and fluorescence microscopy. Using powdered food pellet for laboratory rodents (a common larval food used in the laboratory) as a carrier for C14, loading-release dynamics, larvicidal efficacy and residual activity of the C14-carrier complex were investigated.Main FindingsThe C14 molecule was found to exert a potent photosensitizing activity on Ae. aegypti larvae. At irradiation intervals of 12 h and 1 h, at a light intensity of 4.0 mW/cm2, which is 50–100 times lower than that of natural sunlight, LC50 values of 0.1 µM (0.15 mg/l) and 0.5 µM (0.77 mg/l) were obtained, respectively. The molecule was active after ingestion by the larvae and caused irreversible, lethal damage to the midgut and caecal epithelia. The amphiphilic nature of C14 allowed a formulate to be produced that not only was as active against the larvae as C14 in solution, but also possessed a residual activity of at least two weeks, in laboratory conditions.ConclusionsThe meso-substituted synthetic porphyrin C14, thanks to its photo-sensitizing properties represents an attractive candidate for the development of novel photolarvicides for dengue vector control.