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Tracking the Photosensitizing Antibacterial Activity of Mono(acridyl)bis(arginyl)porphyrin (MABAP) by Time-Resolved Spectroscopy

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. A 2010, 114, 9, 3334-3339
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    Tracking the Photosensitizing Antibacterial Activity of Mono(acridyl)bis(arginyl)porphyrin (MABAP) by Time-Resolved Spectroscopy†
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    Laboratoire de Photophysique Moléculaire, CNRS UPR 3361, Université Paris-Sud, F-91405 Orsay Cedex, Laboratoire de Chimie Bioorganique et Bioinorganique, UMR 8124, ICMMO, Université Paris-Sud, F-91405 Orsay Cedex, and Unité mixte de recherche en Bioadhésion et Hygiène des Matériaux, UMR 763, INRA-AgroParisTech, F-91300 Massy
    †Part of the “Benoît Soep Festschrift”.
    * To whom correspondence should be addressed. E-mail: [email protected]. Fax: 33 (0)1 69 15 67 77.
    ‡Laboratoire de Photophysique Moléculaire, Université Paris-Sud.
    §Laboratoire de Chimie Bioorganique et Bioinorganique, Université Paris-Sud.
    ∥INRA-AgroParisTech.
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2010, 114, 9, 3334–3339
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp910387a
    Published January 13, 2010
    Copyright © 2010 American Chemical Society
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    Abstract

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    Photodynamic inactivation (PDI) is currently receiving interest for its potential as an antimicrobial treatment. Although photosensitizing agents and light have been used for medical purposes for a very long time, only a little information is available about the mechanism of PDI for bacteria. Pseudomonas aeruginosa is a Gram negative bacteria involved in chronic infections in cystic fibrosis patients and also one of the commonest agents of hospital acquired infections. In the present study the sensitivity of Pseudomonas aeruginosa to the phototoxic effects of the mono(acridyl)bis(arginyl)porphyrin (MABAP) has been investigated as well as the photophysical and photochemical properties of this cationic porphyrin complexed to [poly(dG-dC)]2 to investigate the mechanisms that lead to bacteria inactivation. Both picosecond time-resolved fluorescence and femtosecond to nanosecond transient absorption measurements give evidence that while MABAP can react through its triplet state and/or an ultrafast electron transfer with guanine, its intercalation between GC base pairs is not the main target of MABAP photoactivity. The analysis of both fluorescence emission and excitation spectra reveals the occurrence of an energy transfer through the DNA double helix between the acridine and porphyrin chromophores of MABAP, as previously observed for the stacked free molecule in solution. This efficient process may lead to the excitation of twice more porphyrin chromophores in MABAP by comparison to other cationic porphyrins.

    Copyright © 2010 American Chemical Society

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    Cited By

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    This article is cited by 8 publications.

    1. Lukasz Sobotta, Paulina Skupin-Mrugalska, Jaroslaw Piskorz, Jadwiga Mielcarek. Porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria. European Journal of Medicinal Chemistry 2019, 175 , 72-106. https://doi.org/10.1016/j.ejmech.2019.04.057
    2. Páraic M. Keane, John M. Kelly. Transient absorption and time-resolved vibrational studies of photophysical and photochemical processes in DNA-intercalating polypyridyl metal complexes or cationic porphyrins. Coordination Chemistry Reviews 2018, 364 , 137-154. https://doi.org/10.1016/j.ccr.2018.02.018
    3. Lu Jiang, Ching Ruey Raymond Gan, Jian Gao, Xian Jun Loh. A Perspective on the Trends and Challenges Facing Porphyrin‐Based Anti‐Microbial Materials. Small 2016, 12 (27) , 3609-3644. https://doi.org/10.1002/smll.201600327
    4. Beata Girek, Wanda Sliwa. Porphyrins functionalized by quaternary pyridinium units. Journal of Porphyrins and Phthalocyanines 2013, 17 (12) , 1139-1156. https://doi.org/10.1142/S1088424613300085
    5. Ádám Orosz, Gábor Mező, Levente Herényi, Jan Habdas, Zsuzsa Majer, Beata Myśliwa-Kurdziel, Katalin Tóth, Gabriella Csík. Binding of new cationic porphyrin–tetrapeptide conjugates to nucleoprotein complexes. Biophysical Chemistry 2013, 177-178 , 14-23. https://doi.org/10.1016/j.bpc.2013.03.003
    6. Oxana A. Kovaleva, Vladimir B. Tsvetkov, Anna K. Shchyolkina, Olga F. Borisova, Valentina A. Ol’shevskaya, Anton V. Makarenkov, Alexander S. Semeikin, Alexander A. Shtil, Dmitry N. Kaluzhny. The role of carboxymethyl substituents in the interaction of tetracationic porphyrins with DNA. European Biophysics Journal 2012, 41 (9) , 723-732. https://doi.org/10.1007/s00249-012-0848-y
    7. Bartłomiej Białkowski, Yuriy Stepanenko, Michał Nejbauer, Czesław Radzewicz, Jacek Waluk. The dynamics and origin of the unrelaxed fluorescence of free-base tetraphenylporphyrin. Journal of Photochemistry and Photobiology A: Chemistry 2012, 234 , 100-106. https://doi.org/10.1016/j.jphotochem.2011.10.026
    8. Natalia Sergeeva, Mathias Senge. Photochemical Transformations Involving Porphyrins and Phthalocyanines. 2012, 831-879. https://doi.org/10.1201/b12252-35
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2010, 114, 9, 3334–3339
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp910387a
    Published January 13, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

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