Photophysical and Bactericidal Properties of Pyridinium and Imidazolium Porphyrins for Photodynamic Antimicrobial Chemotherapy

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Mar 6

PMID 33672630

Citations 7

Authors

Florent Le Guern

Tan-Sothea Ouk

Issabayev Yerzhan

Yesmurzayeva Nurlykyz

Philippe Arnoux

Celine Frochot

Stephanie Leroy-Lhez

Vincent Sol

Affiliations

Soon will be listed here.

Abstract

Despite advances achieved over the last decade, infections caused by multi-drug-resistant bacterial strains are increasingly becoming important societal issues that need to be addressed. New approaches have already been developed in order to overcome this problem. Photodynamic antimicrobial chemotherapy (PACT) could provide an alternative to fight infectious bacteria. Many studies have highlighted the value of cationic photosensitizers in order to improve this approach. This study reports the synthesis and the characterization of cationic porphyrins derived from methylimidazolium and phenylimidazolium porphyrins, along with a comparison of their photophysical properties with the well-known -methylpyridyl (pyridinium) porphyrin family. PACT tests conducted with the tetracationic porphyrins of these three families showed that these new photosensitizers may offer a good alternative to the classical pyridinium porphyrins, especially against and . In addition, they pave the way to new cationic photosensitizers by the means of derivatization through amide bond formation.

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References

Dougherty T, Gomer C, Henderson B, Jori G, Kessel D, Korbelik M . Photodynamic therapy. J Natl Cancer Inst. 1998; 90(12):889-905. PMC: 4592754. DOI: 10.1093/jnci/90.12.889. View

Reddi E, Ceccon M, Valduga G, Jori G, Bommer J, Elisei F . Photophysical properties and antibacterial activity of meso-substituted cationic porphyrins. Photochem Photobiol. 2002; 75(5):462-70. DOI: 10.1562/0031-8655(2002)075<0462:ppaaao>2.0.co;2. View

Dysart J, Patterson M . Characterization of Photofrin photobleaching for singlet oxygen dose estimation during photodynamic therapy of MLL cells in vitro. Phys Med Biol. 2005; 50(11):2597-616. DOI: 10.1088/0031-9155/50/11/011. View

Le Guern F, Sol V, Ouk C, Arnoux P, Frochot C, Ouk T . Enhanced Photobactericidal and Targeting Properties of a Cationic Porphyrin following the Attachment of Polymyxin B. Bioconjug Chem. 2017; 28(9):2493-2506. DOI: 10.1021/acs.bioconjchem.7b00516. View

Alves E, Faustino M, Neves M, Cunha A, Tome J, Almeida A . An insight on bacterial cellular targets of photodynamic inactivation. Future Med Chem. 2014; 6(2):141-64. DOI: 10.4155/fmc.13.211. View

Kumar D, Chandra Shekar K, Mishra B, Kurihara R, Ogura M, Ito T . Cationic porphyrin-quinoxaline conjugate as a photochemically triggered novel cytotoxic agent. Bioorg Med Chem Lett. 2013; 23(11):3221-4. DOI: 10.1016/j.bmcl.2013.03.126. View

Wainwright M, Maisch T, Nonell S, Plaetzer K, Almeida A, Tegos G . Photoantimicrobials-are we afraid of the light?. Lancet Infect Dis. 2016; 17(2):e49-e55. PMC: 5280084. DOI: 10.1016/S1473-3099(16)30268-7. View

Le Guern F, Ouk T, Ouk C, Vanderesse R, Champavier Y, Pinault E . Lysine Analogue of Polymyxin B as a Significant Opportunity for Photodynamic Antimicrobial Chemotherapy. ACS Med Chem Lett. 2018; 9(1):11-16. PMC: 5767886. DOI: 10.1021/acsmedchemlett.7b00360. View

Jacobs R, Stranius K, Maligaspe E, Lemmetyinen H, Tkachenko N, Zandler M . Syntheses and excitation transfer studies of near-orthogonal free-base porphyrin-ruthenium phthalocyanine dyads and pentad. Inorg Chem. 2012; 51(6):3656-65. DOI: 10.1021/ic202574q. View

10.

Mathai S, Smith T, Ghiggino K . Singlet oxygen quantum yields of potential porphyrin-based photosensitisers for photodynamic therapy. Photochem Photobiol Sci. 2007; 6(9):995-1002. DOI: 10.1039/b705853e. View

11.

Ventola C . The antibiotic resistance crisis: part 1: causes and threats. P T. 2015; 40(4):277-83. PMC: 4378521. View

12.

Minnock A, Vernon D, Schofield J, Griffiths J, Parish J, Brown S . Mechanism of uptake of a cationic water-soluble pyridinium zinc phthalocyanine across the outer membrane of Escherichia coli. Antimicrob Agents Chemother. 2000; 44(3):522-7. PMC: 89720. DOI: 10.1128/AAC.44.3.522-527.2000. View

13.

Tavares A, Carvalho C, Faustino M, Neves M, Tome J, Tome A . Antimicrobial photodynamic therapy: study of bacterial recovery viability and potential development of resistance after treatment. Mar Drugs. 2010; 8(1):91-105. PMC: 2817925. DOI: 10.3390/md8010091. View

14.

Tim M . Strategies to optimize photosensitizers for photodynamic inactivation of bacteria. J Photochem Photobiol B. 2015; 150:2-10. DOI: 10.1016/j.jphotobiol.2015.05.010. View

15.

Mbakidi J, Herke K, Alves S, Chaleix V, Granet R, Krausz P . Synthesis and photobiocidal properties of cationic porphyrin-grafted paper. Carbohydr Polym. 2012; 91(1):333-8. DOI: 10.1016/j.carbpol.2012.08.013. View

16.

Sol V, Branland P, Granet R, Kaldapa C, Verneuil B, Krausz P . Nitroglycosylated meso-arylporphyrins as photoinhibitors of gram positive bacteria. Bioorg Med Chem Lett. 1999; 8(21):3007-10. DOI: 10.1016/S0960-894X(98)00536-8. View

17.

Tjahjono D, Akutsu T, Yoshioka N, Inoue H . Cationic porphyrins bearing diazolium rings: synthesis and their interaction with calf thymus DNA. Biochim Biophys Acta. 1999; 1472(1-2):333-43. DOI: 10.1016/s0304-4165(99)00139-7. View

18.

Prasanth C, Karunakaran S, Paul A, Kussovski V, Mantareva V, Ramaiah D . Antimicrobial photodynamic efficiency of novel cationic porphyrins towards periodontal Gram-positive and Gram-negative pathogenic bacteria. Photochem Photobiol. 2013; 90(3):628-40. DOI: 10.1111/php.12198. View

19.

Saino E, Sbarra M, Arciola C, Scavone M, Bloise N, Nikolov P . Photodynamic action of Tri-meso (N-methyl-pyridyl), meso (N-tetradecyl-pyridyl) porphine on Staphylococcus epidermidis biofilms grown on Ti6Al4V alloy. Int J Artif Organs. 2010; 33(9):636-45. DOI: 10.1177/039139881003300909. View

20.

Detty M, Gibson S, Wagner S . Current clinical and preclinical photosensitizers for use in photodynamic therapy. J Med Chem. 2004; 47(16):3897-915. DOI: 10.1021/jm040074b. View