Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents
New porphyrin–Schiff base conjugates bearing one (<b>6</b>) and two (<b>7</b>) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(<i>N</i>,<i>N</i>-dimethylamino)propoxy)benzaldehyd...
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| Format: | Article |
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MDPI AG
2021-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/19/5877 |
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| author | María E. Pérez Javier E. Durantini Eugenia Reynoso María G. Alvarez María E. Milanesio Edgardo N. Durantini |
| author_facet | María E. Pérez Javier E. Durantini Eugenia Reynoso María G. Alvarez María E. Milanesio Edgardo N. Durantini |
| author_sort | María E. Pérez |
| collection | DOAJ |
| description | New porphyrin–Schiff base conjugates bearing one (<b>6</b>) and two (<b>7</b>) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(<i>N</i>,<i>N</i>-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission (Φ<sub>F</sub> ~ 0.12) in <i>N</i>,<i>N</i>-dimethylformamide. Porphyrins <b>6</b> and <b>7</b> photosensitized the generation of O<sub>2</sub>(<sup>1</sup>Δ<sub>g</sub>) (Φ<sub>Δ</sub> ~ 0.44) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly mediated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photodynamic action through a reaction with O<sub>2</sub>(<sup>1</sup>Δ<sub>g</sub>) to produce iodine. The photodynamic inactivation capacity induced by porphyrins <b>6</b> and <b>7</b> was evaluated in <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i>. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms. |
| first_indexed | 2024-03-10T06:55:25Z |
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| id | doaj.art-d1b05e521f8747b1bcd0a57e54307244 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:55:25Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d1b05e521f8747b1bcd0a57e543072442023-11-22T16:33:58ZengMDPI AGMolecules1420-30492021-09-012619587710.3390/molecules26195877Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic AgentsMaría E. Pérez0Javier E. Durantini1Eugenia Reynoso2María G. Alvarez3María E. Milanesio4Edgardo N. Durantini5IDAS-CONICET, Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, Río Cuarto X5804BYA, Córdoba, ArgentinaIITEMA, Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, Río Cuarto X5804BYA, Córdoba, ArgentinaIDAS-CONICET, Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, Río Cuarto X5804BYA, Córdoba, ArgentinaIDAS-CONICET, Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, Río Cuarto X5804BYA, Córdoba, ArgentinaIDAS-CONICET, Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, Río Cuarto X5804BYA, Córdoba, ArgentinaIDAS-CONICET, Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, Río Cuarto X5804BYA, Córdoba, ArgentinaNew porphyrin–Schiff base conjugates bearing one (<b>6</b>) and two (<b>7</b>) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(<i>N</i>,<i>N</i>-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission (Φ<sub>F</sub> ~ 0.12) in <i>N</i>,<i>N</i>-dimethylformamide. Porphyrins <b>6</b> and <b>7</b> photosensitized the generation of O<sub>2</sub>(<sup>1</sup>Δ<sub>g</sub>) (Φ<sub>Δ</sub> ~ 0.44) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly mediated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photodynamic action through a reaction with O<sub>2</sub>(<sup>1</sup>Δ<sub>g</sub>) to produce iodine. The photodynamic inactivation capacity induced by porphyrins <b>6</b> and <b>7</b> was evaluated in <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i>. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms.https://www.mdpi.com/1420-3049/26/19/5877porphyrinSchiff basephotodynamic inactivationreactive oxygen speciesphotoinactivationmicroorganism |
| spellingShingle | María E. Pérez Javier E. Durantini Eugenia Reynoso María G. Alvarez María E. Milanesio Edgardo N. Durantini Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents Molecules porphyrin Schiff base photodynamic inactivation reactive oxygen species photoinactivation microorganism |
| title | Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents |
| title_full | Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents |
| title_fullStr | Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents |
| title_full_unstemmed | Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents |
| title_short | Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents |
| title_sort | porphyrin schiff base conjugates bearing basic amino groups as antimicrobial phototherapeutic agents |
| topic | porphyrin Schiff base photodynamic inactivation reactive oxygen species photoinactivation microorganism |
| url | https://www.mdpi.com/1420-3049/26/19/5877 |
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