Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i>
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 single...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/2/464 |
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| author | Bruno M. F. Ladeira Cristina J. Dias Ana T. P. C. Gomes Augusto C. Tomé Maria G. P. M. S. Neves Nuno M. M. Moura Adelaide Almeida M. Amparo F. Faustino |
| author_facet | Bruno M. F. Ladeira Cristina J. Dias Ana T. P. C. Gomes Augusto C. Tomé Maria G. P. M. S. Neves Nuno M. M. Moura Adelaide Almeida M. Amparo F. Faustino |
| author_sort | Bruno M. F. Ladeira |
| collection | DOAJ |
| description | 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 <i>E. coli</i>. 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 <i>E. coli</i> photoinactivation profile. |
| first_indexed | 2024-03-09T04:32:22Z |
| format | Article |
| id | doaj.art-ded9c4be08984c8e867ec2041c76e04d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:32:22Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ded9c4be08984c8e867ec2041c76e04d2023-12-03T13:34:02ZengMDPI AGMolecules1420-30492021-01-0126246410.3390/molecules26020464Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i>Bruno M. F. Ladeira0Cristina J. Dias1Ana T. P. C. Gomes2Augusto C. Tomé3Maria G. P. M. S. Neves4Nuno M. M. Moura5Adelaide Almeida6M. Amparo F. Faustino7LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalCESAM, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalCESAM, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalNew 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 <i>E. coli</i>. 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 <i>E. coli</i> photoinactivation profile.https://www.mdpi.com/1420-3049/26/2/464porphyrincycloadditiondipolarophilephotodynamic inactivationphotosensitizer<i>E. coli</i> |
| spellingShingle | Bruno M. F. Ladeira Cristina J. Dias Ana T. P. C. Gomes Augusto C. Tomé Maria G. P. M. S. Neves Nuno M. M. Moura Adelaide Almeida M. Amparo F. Faustino Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i> Molecules porphyrin cycloaddition dipolarophile photodynamic inactivation photosensitizer <i>E. coli</i> |
| title | Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i> |
| title_full | Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i> |
| title_fullStr | Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i> |
| title_full_unstemmed | Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i> |
| title_short | Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against <i>E. coli</i> |
| title_sort | cationic pyrrolidine pyrroline substituted porphyrins as efficient photosensitizers against i e coli i |
| topic | porphyrin cycloaddition dipolarophile photodynamic inactivation photosensitizer <i>E. coli</i> |
| url | https://www.mdpi.com/1420-3049/26/2/464 |
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