Photophysical and Bactericidal Properties of Pyridinium and Imidazolium Porphyrins for Photodynamic Antimicrobial Chemotherapy
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. Photophysical Properties
2.3. Singlet Oxygen Production
2.4. Bacterial Photoinactivation
3. Materials and Methods
3.1. General Methods
3.2. Chemical Synthesis
3.2.1. Preparation of Ethyl 4-Formylphenoxyacetate
3.2.2. General Procedure for the Synthesis of Porphyrins
3.2.3. General Procedure for the Deprotection of Carboxylic Acid
3.2.4. General Procedure for the N-Methylation of Porphyrins
3.2.5. Synthesis of 5-(4-minophenyl)-10,15,20-tri(4-pyridyl)-21H,23H-porphyrin (1d)
3.2.6. Synthesis of 5-(4-aminophenyl)-10,15,20-tri(4-N-methylpyridyl)-21H,23H-porphyrin (2d)
3.3. Spectroscopic Measurements
3.4. Bacterial Cultures
3.5. Bacterial Photoinactivation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Neutral Porphyrins | Cationic Porphyrins | ||||
n | A | B | Compound a | Methylated A | Compound a |
4 | - | 1a [47,48] | 2a [47,48] | ||
3 | 1b [49,50] | 2b [51,52] | |||
3 | 1d [53] | 2d [44] | |||
4 | - | 3a [54,55] | 4a [32] | ||
3 | 3b | 4b | |||
3 | 3c | 4c | |||
4 | - | 5a [30] | 6a [30,56] | ||
3 | 5b | 6b | |||
2 | 5e (isomer mixture) [57] | 6e (isomer mixture) |
Type | Porphyrin | Average Yield (%) |
---|---|---|
A4 | 1a | 10 |
3a | 15 | |
5a | 2 | |
A3B | 1b | 5 |
1d | 2 | |
3b | 13 | |
3c | 10 | |
5b | 5 | |
A2B2 | 5e | 5 |
λmax (nm) (log ε; L mol−1 cm−1) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Compd | Soret | Qy(1,0) | Qy(0,0) | Qx(1,0) | Qx(0,0) | Compd | Soret | Qy(1,0) | Qy(0,0) | Qx(1,0) | Qx(0,0) |
1a | 414 (3.92) | 509 (2.56) | 546 (2.00) | 588 (2.00) | 645 (1.75) | 4a | 416 (5.62) | 513 (4.24) | 547 (3.86) | 590 (3.71) | 645 (3.45) |
1b | 415 (5.10) | 512 (3.86) | 544 (3.51) | 589 (3.44) | 645 (3.15) | 4b | 417 (5.67) | 513 (4.30) | 547 (3.94) | 590 (3.78) | 646 (3.57) |
1d | 416 (4.82) | 519 (3.93) | 555 (3.78) | 594 (3.67) | 655 (3.54) | 4c | 418 (5.57) | 514 (4.20) | 549 (3.89) | 591 (3.69) | 649 (3.55) |
2a | 415 (5.16) | 524 (4.44) | 556 (4.26) | 594 (4.19) | 646 (3.87) | 5a | 416 (5.44) | 509 (4.24) | 543 (3.48) | 585 (3.75) | 658 (3.63) |
2b | 426 (5.40) | 517 (4.26) | 554 (3.91) | 592 (3.82) | 649 (3.43) | 5b | 415 (5.28) | 510 (4.04) | 543 (3.36) | 586 (3.54) | 655 (3.20) |
2d | 428 (5.16) | 520 (4.10) | 566 (3.93) | 593 (3.92) | 657 (3.54) | 5e | 415 (5.45) | 511 (4.12) | 545 (3.52) | 586 (3.62) | 650 (3.01) |
3a | 417 (3.71) | 516 (2.22) | 558 (2.09) | 592 (1.97) | 650 (1.91) | 6a | 415 (4.58) | 510 (3.41) | 545 (3.25) | 582 (3.32) | 637 (3.08) |
3b | 417 (5.14) | 515 (3.80) | 549 (3.55) | 592 (3.36) | 648 (3.28) | 6b | 416 (5.42) | 510 (4.23) | 542 (3.66) | 583 (3.86) | 634 (3.69) |
3c | 418 (5.23) | 516 (4.07) | 555 (3.92) | 593 (3.78) | 652 (3.74) | 6e | 417 (5.59) | 514 (4.35) | 544 (3.68) | 583 (3.97) | 632 (3.21) |
Ethanol | D2O | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Compd | λf1 a (nm) | λf2 b (nm) | λf1/λf2 | ΦF c | ΦΔ d | τF (ns) | τΔ e (µs) | λf1 a (nm) | λf2 b (nm) | λf1/λf2 | ΦF c | ΦΔ f | τF (ns) | τΔ g (µs) |
1a | 645 | 712 | 0.75 | 0.10 | 0.74 | 10.0 | 15 | − | − | − | − | − | − | − |
1b | 646 | 713 | 1.06 | 0.12 | 0.77 | 10.1 | 17 | − | − | − | − | − | − | − |
1d | 663 | 716 | 1.29 | 0.02 | 0.05 | 3.2 (57%) | 16 | − | − | − | − | − | − | − |
8.5 (43%) | ||||||||||||||
2a | 645 | 713 | 0.75 | 0.09 | 0.65 | 10.0 | 16 | 657 | 709 | 0.63 | 0.07 | 0.90 | 6.1 | 69 |
2b | 656 | 716 | 1.27 | 0.12 | 0.82 | 8.9 | 16 | 655 | 709 | 0.59 | 0.07 | 0.93 | 4.8 | 66 |
2d | 654 | 719 | 0.97 | 0 | 0 | nd | nd | nd | nd | nd | 0.01 | nd | 4.6 | nd |
3a | 652 | 718 | 1.89 | 0.13 | 0.66 | 9.5 | 16 | − | − | − | − | − | − | − |
3b | 650 | 717 | 1.7 | 0.09 | 0.57 | 10.1 | 17 | − | − | − | − | − | − | − |
3c | 653 | 719 | 2.05 | 0.08 | 0.49 | 9.8 | 16 | − | − | − | − | − | − | − |
− | − | − | − | − | − | − | ||||||||
4a | 648 | 716 | 1.3 | 0.06 | 0.51 | 10 | 16 | 644 | 704 | 1.33 | 0.14 | 0.83 | 11.2 | 65 |
4b | 649 | 716 | 1.43 | 0.07 | 0.54 | 9.4 | 15 | 660 | 719 | 1.45 | 0.01 | nd | 10.8 | nd |
4c | 651 | 718 | 1.7 | 0.07 | 0.53 | 9.6 | 16 | 648 | 707 | 1.53 | 0.14 | 0.62 | 10.1 | 68 |
5a | 648 | 714 | 1.26 | 0.14 | 0.74 | 8.7 | 15 | − | − | − | − | − | − | − |
5b | 650 | 714 | 1.25 | 0.15 | 0.78 | 12.3 | 16 | − | − | − | − | − | − | − |
5e | 649 | 711 | 0.62 | 0.10 | 0.81 | 9.7 | 15 | − | − | − | − | − | − | − |
− | − | − | − | − | − | − | ||||||||
6a | 639 | 709 | 1.75 | 0.13 | 0.63 | 12.7 | 17 | 635 | 702 | 2.66 | 0.15 | 0.60 | 17.4 | 60 |
6b | 638 | 705 | 1.73 | 0.13 | 0.58 | 10.4 | 15 | 636 | 702 | 1.53 | 0.13 | 0.83 | 16.1 | 67 |
6e | 639 | 704 | 0.39 | 0.11 | 0.78 | 11.9 | 15 | 638 | 698 | 0.39 | 0.09 | 0.86 | 14.9 | 69 |
MBC (μM) | 2a | 4a | 6a |
---|---|---|---|
S. aureus | 5.0 | 1.5 | 6.2 |
E. coli | 18.0 | 2.5 | 40.0 |
P. aeruginosa | 20.0 | 22.0 | 25.0 |
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Le Guern, F.; Ouk, T.-S.; Yerzhan, I.; Nurlykyz, Y.; Arnoux, P.; Frochot, C.; Leroy-Lhez, S.; Sol, V. Photophysical and Bactericidal Properties of Pyridinium and Imidazolium Porphyrins for Photodynamic Antimicrobial Chemotherapy. Molecules 2021, 26, 1122. https://doi.org/10.3390/molecules26041122
Le Guern F, Ouk T-S, Yerzhan I, Nurlykyz Y, Arnoux P, Frochot C, Leroy-Lhez S, Sol V. Photophysical and Bactericidal Properties of Pyridinium and Imidazolium Porphyrins for Photodynamic Antimicrobial Chemotherapy. Molecules. 2021; 26(4):1122. https://doi.org/10.3390/molecules26041122
Chicago/Turabian StyleLe Guern, Florent, Tan-Sothéa Ouk, Issabayev Yerzhan, Yesmurzayeva Nurlykyz, Philippe Arnoux, Céline Frochot, Stéphanie Leroy-Lhez, and Vincent Sol. 2021. "Photophysical and Bactericidal Properties of Pyridinium and Imidazolium Porphyrins for Photodynamic Antimicrobial Chemotherapy" Molecules 26, no. 4: 1122. https://doi.org/10.3390/molecules26041122