Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against E. coli. 2021

Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.

New porphyrin-pyrrolidine/pyrroline conjugates were prepared by revisiting 1,3-dipolar cycloaddition reactions between a porphyrinic azomethine ylide and a series of dipolarophiles. Cationic conjugates obtained by alkylation of the pyrrolidine/pyrroline cycloadducts showed ability to generate singlet oxygen and to produce iodine in presence of KI when irradiated with visible light. Some of the cationic derivatives showed photobactericidal properties towards a Gram-negative bioluminescent E. coli. In all cases, these features were significantly improved using KI as coadjutant, allowing, under the tested conditions, the photoinactivation of the bacterium until the detection limit of the method with a drastic reduction of the required photosensitizer concentration and irradiation time. The obtained results showed a high correlation between the ability of the cationic porphyrin derivative to produce singlet oxygen and iodine and its E. coli photoinactivation profile.

UI MeSH Term Description Entries
D011166 Porphyrins A group of compounds containing the porphin structure, four pyrrole rings connected by methine bridges in a cyclic configuration to which a variety of side chains are attached. The nature of the side chain is indicated by a prefix, as uroporphyrin, hematoporphyrin, etc. The porphyrins, in combination with iron, form the heme component in biologically significant compounds such as hemoglobin and myoglobin. Porphyrin
D011758 Pyrroles Azoles of one NITROGEN and two double bonds that have aromatic chemical properties. Pyrrole
D004926 Escherichia coli A species of gram-negative, facultatively anaerobic, rod-shaped bacteria (GRAM-NEGATIVE FACULTATIVELY ANAEROBIC RODS) commonly found in the lower part of the intestine of warm-blooded animals. It is usually nonpathogenic, but some strains are known to produce DIARRHEA and pyogenic infections. Pathogenic strains (virotypes) are classified by their specific pathogenic mechanisms such as toxins (ENTEROTOXIGENIC ESCHERICHIA COLI), etc. Alkalescens-Dispar Group,Bacillus coli,Bacterium coli,Bacterium coli commune,Diffusely Adherent Escherichia coli,E coli,EAggEC,Enteroaggregative Escherichia coli,Enterococcus coli,Diffusely Adherent E. coli,Enteroaggregative E. coli,Enteroinvasive E. coli,Enteroinvasive Escherichia coli
D000900 Anti-Bacterial Agents Substances that inhibit the growth or reproduction of BACTERIA. Anti-Bacterial Agent,Anti-Bacterial Compound,Anti-Mycobacterial Agent,Antibacterial Agent,Antibiotics,Antimycobacterial Agent,Bacteriocidal Agent,Bacteriocide,Anti-Bacterial Compounds,Anti-Mycobacterial Agents,Antibacterial Agents,Antibiotic,Antimycobacterial Agents,Bacteriocidal Agents,Bacteriocides,Agent, Anti-Bacterial,Agent, Anti-Mycobacterial,Agent, Antibacterial,Agent, Antimycobacterial,Agent, Bacteriocidal,Agents, Anti-Bacterial,Agents, Anti-Mycobacterial,Agents, Antibacterial,Agents, Antimycobacterial,Agents, Bacteriocidal,Anti Bacterial Agent,Anti Bacterial Agents,Anti Bacterial Compound,Anti Bacterial Compounds,Anti Mycobacterial Agent,Anti Mycobacterial Agents,Compound, Anti-Bacterial,Compounds, Anti-Bacterial
D017319 Photosensitizing Agents Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. Photosensitizer,Photosensitizers,Photosensitizing Agent,Photosensitizing Effect,Photosensitizing Effects,Agent, Photosensitizing,Agents, Photosensitizing,Effect, Photosensitizing,Effects, Photosensitizing
D026082 Singlet Oxygen An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages. Singlet Dioxygen,Dioxygen, Singlet,Oxygen, Singlet

Related Publications

Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
February 1996, Journal of photochemistry and photobiology. B, Biology,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
May 1993, Journal of photochemistry and photobiology. B, Biology,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
January 1989, Ciba Foundation symposium,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
March 2021, ACS medicinal chemistry letters,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
April 2024, Dalton transactions (Cambridge, England : 2003),
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
August 2004, Journal of the American Chemical Society,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
August 2018, Future medicinal chemistry,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
March 1992, Nucleic acids research,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
May 2002, Photochemistry and photobiology,
Bruno M F Ladeira, and Cristina J Dias, and Ana T P C Gomes, and Augusto C Tomé, and Maria G P M S Neves, and Nuno M M Moura, and Adelaide Almeida, and M Amparo F Faustino
August 2002, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology,
Copied contents to your clipboard!