New cationic diketopyrrolopyrrole photosensitizers for the photoinactivation of gram-negative and gram-positive bacteria

Salam, M. A., Al-Amin, M. Y., Salam, M. T., Pawar, J. S., Akhter, N., Rabaan, A. A., & Alqumber, M. A. A. (2023). Antimicrobial resistance: A growing serious threat for global public health. Healthcare, 11, 1946. https://doi.org/10.3390/healthcare11131946

Article  PubMed  PubMed Central  Google Scholar 

Ahmed, S. K., Hussein, S., Qurbani, K., Ibrahim, R. H., Fareeq, A., Mahmood, K. A., & Mohamed, M. G. (2024). Antimicrobial resistance: Impacts, challenges, and future prospects. Journal of Medicine Surgery and Public Health, 2, 100081. https://doi.org/10.1016/j.glmedi.2024.100081

Article  Google Scholar 

Kolarikova, M., Hosikova, B., Dilenko, H., Barton-Tomankova, K., Valkova, L., Bajgar, R., Malina, L., & Kolarova, H. (2023). Photodynamic therapy: Innovative approaches for antibacterial and anticancer treatments. Medicinal Research Reviews, 43, 717–774. https://doi.org/10.1002/med.21935

Article  CAS  PubMed  Google Scholar 

Yuan, B., Liu, J., Guan, R., Jin, C., Ji, L., & Chao, H. (2019). Endoplasmic reticulum targeted cyclometalated iridium(iii) complexes as efficient photodynamic therapy photosensitizers. Dalton Transactions, 48, 6408–6415. https://doi.org/10.1039/c9dt01072f

Article  CAS  PubMed  Google Scholar 

Simões, J. C. S., Sarpaki, S., Papadimitroulas, P., Therrien, B., & Loudos, G. (2020). Conjugated photosensitizers for imaging and PDT in cancer research. Journal of Medicinal Chemistry, 63, 14119–14150. https://doi.org/10.1021/acs.jmedchem.0c00047

Article  CAS  PubMed  Google Scholar 

Agazzi, M. L., Ballatore, M. B., Durantini, A. M., Durantini, E. N., & Tomé, A. C. (2019). BODIPYs in antitumoral and antimicrobial photodynamic therapy: An integrating review. Photochem Photobiol C: Photochem Rev, 40, 21–48. https://doi.org/10.1016/j.jphotochemrev.2019.04.001

Article  CAS  Google Scholar 

Tursynova, N., Helena Maliszewska, I., Jóźwiak, K., Sokolnicki, J., Kochel, A., Lipkowski, P., Bartkiewicz, S., & Filarowski, A. (2024). The photoinactivation of pathogenic bacteria using synthesized benzodioxole-BODIPY dyes. Journal of Photochemistry and Photobiology. A, Chemistry, 450, 115474. https://doi.org/10.1016/j.jphotochem.2024.115474

Article  CAS  Google Scholar 

Gonzalez Lopez, E. J., Sarotti, A. M., Martínez, S. R., Macor, L. P., Durantini, J. E., Renfige, M., Gervaldo, M. A., Otero, L. A., Durantini, A. M., Durantini, E. N., & Heredia, D. A. (2022). BOPHY-Fullerene C60 dyad as a photosensitizer for antimicrobial photodynamic therapy. Chemistry--A European Journal, 28, e202103884. https://doi.org/10.1002/chem.202103884

Article  CAS  PubMed  Google Scholar 

Heredia, D. A., Durantini, A. M., Durantini, J. E., & Durantini, E. N. (2022). Fullerene C60 derivatives as antimicrobial photodynamic agents. Photochem Photobiol C: Photochem Rev, 51, 100471. https://doi.org/10.1016/j.jphotochemrev.2021.100471

Article  CAS  Google Scholar 

Hamblin, M. R., & Abrahamse, H. (2020). Oxygen-Independent antimicrobial photoinactivation: Type III photochemical mechanism? Antibiotics, 9, 53. https://doi.org/10.3390/antibiotics9020053

Article  CAS  PubMed  PubMed Central  Google Scholar 

Yan, E., Kwek, G., Qing, N. S., Lingesh, S., & Xing, B. (2023). Antimicrobial photodynamic therapy for the remote eradication of bacteria. Chempluschem, 88, e202300009. https://doi.org/10.1002/cplu.202300009

Article  CAS  PubMed  Google Scholar 

Marasini, S., Leanse, L. G., & Dai, T. (2021). Can microorganisms develop resistance against light based anti-infective agents? Advanced Drug Delivery Reviews, 175, 113822. https://doi.org/10.1016/j.addr.2021.05.032

Article  CAS  PubMed  Google Scholar 

Agazzi, M. L., Almodovar, V. A. S., Gsponer, N. S., Bertolotti, S., Tomé, A. C., & Durantini, E. N. (2020). Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity. Organic & Biomolecular Chemistry, 18, 1449–1461. https://doi.org/10.1039/c9ob02487e

Article  CAS  Google Scholar 

Schmitt, J., Heitz, V., Sour, A., Bolze, F., Kessler, P., Flamigni, L., Ventura, B., Bonnet, C. S., & Tóth, É. (2016). A theranostic agent combining a Two-Photon-Absorbing photosensitizer for photodynamic therapy and a Gadolinium(III) complex for MRI detection. Chemistry--A European Journal, 22, 2775–2786. https://doi.org/10.1002/chem.201503433

Article  CAS  PubMed  Google Scholar 

Pérez, M. E., Almodovar, V. A. S., Durantini, J. E., Gsponer, N. S., Durantini, A. M., Tomé, A. C., & Durantini, E. N. (2023). Diketopyrrolopyrrole derivatives as photosensitizing agents against Staphylococcus aureus. Photochemistry and Photobiology, 99, 1131–1141. https://doi.org/10.1111/php.13741

Article  CAS  PubMed  Google Scholar 

Costa, L. D., Vieira, C., Hackbarth, S., Neves, M. G. P. M. S., Almeida, A., Faustino, M. A. F., & Tomé, A. C. (2026). Photodynamic inactivation of Escherichia coli and Staphylococcus aureus by cationic Diketopyrrolopyrroles. Dyes and Pigments, 244, 113101. https://doi.org/10.1016/j.dyepig.2025.113101

Article  CAS  Google Scholar 

Shankar, N., Soe, P. M., & Tam, C. C. (2020). Prevalence and risk of acquisition of methicillin-resistant Staphylococcus aureus among households: A systematic review. International Journal of Infectious Diseases : Ijid : official Publication of the International Society for Infectious Diseases, 92, 105–113. https://doi.org/10.1016/j.ijid.2020.01.008

Article  CAS  PubMed  Google Scholar 

Zhou, S., Rao, Y., Li, J., Huang, Q., & Rao, X. (2022). Staphylococcus aureus small-colony variants: Formation, infection, and treatment. Microbiological Research, 260, 127040. https://doi.org/10.1016/j.micres.2022.127040

Article  CAS  PubMed  Google Scholar 

Rojas, A., Palacios-Baena, Z. R., López-Cortés, L. E., & Rodríguez-Baño, J. (2019). Rates, predictors and mortality of community-onset bloodstream infections due to Pseudomonas aeruginosa: Systematic review and meta-analysis. Clinical Microbiology & Infection, 25, 964–970. https://doi.org/10.1016/j.cmi.2019.04.005

Article  CAS  Google Scholar 

Zhou, F., Lin, S., Zhang, J., Kong, Z., Tan, B. K., Hamzah, S. S., & Hu, J. (2022). Enhancement of photodynamic bactericidal activity of Curcumin against Pseudomonas aeruginosa using polymyxin B. Photodiagnosis Photodyn Ther, 37, 102677. https://doi.org/10.1016/j.pdpdt.2021.102677

Article  CAS  PubMed  Google Scholar 

Almodovar, V. A. S., & Tomé, A. C. (2024). A new platform for the synthesis of Diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions. Beilstein Journal of Organic Chemistry, 20, 1933–1939. https://doi.org/10.3762/bjoc.20.169

Article  CAS  PubMed  PubMed Central  Google Scholar 

Vieira, C., Santos, A., Mesquita, M. Q., Gomes, A. T. P. C., Neves, M. G. P. M. S., Faustino, M. A. F., & Almeida, A. (2019). Advances in aPDT based on the combination of a porphyrinic formulation with potassium iodide: Effectiveness on bacteria and fungi planktonic/biofilm forms and viruses. Journal of Porphyrins and Phthalocyanines, 23, 534–545. https://doi.org/10.1142/S1088424619500408

Article  CAS  Google Scholar 

Vieira, A., Silva, Y. J., Cunha, Â., Gomes, N. C. M., Ackermann, H. W., & Almeida, A. (2012). Phage therapy to control multidrug-resistant Pseudomonas aeruginosa skin Infections: In vitro and ex vivo experiments. European Journal of Clinical Microbiology and Infectious Diseases, 31, 3241–3249. https://doi.org/10.1007/s10096-012-1691-x

Article  CAS  PubMed  Google Scholar 

Vieira, C., Gomes, A. T. P. C., Mesquita, M. Q., Moura, N. M. M., Neves, M. G. P. M. S., Faustino, M. A. F., & Almeida, A. (2018). An insight into the potentiation effect of potassium iodide on aPDT efficacy. Frontiers in Microbiology, 9. https://doi.org/10.3389/fmicb.2018.02665

J.C.J.M.D, S., Menezes, M. A. F., Faustino, K. T., de Oliveira, M. P., Uliana, V. F., Ferreira, S., Hackbarth, B., Röder, T., Teixeira Tasso, T., Furuyama, N., Kobayashi, A. M. S., Silva, M. G. P. M. S., Neves, J. A. S., & Cavaleiro (2014). Synthesis of new Chlorin e 6 trimethyl and Protoporphyrin IX dimethyl ester derivatives and their photophysical and electrochemical characterizations. Chemistry--A European Journal, 20, 13644–13655. https://doi.org/10.1002/chem.201403214

Article  CAS  Google Scholar 

Kuwabara, J., Yamagata, T., & Kanbara, T. (2010). Solid-state structure and optical properties of highly fluorescent Diketopyrrolopyrrole derivatives synthesized by cross-coupling reaction. Tetrahedron, 66, 3736–3741. https://doi.org/10.1016/j.tet.2010.03.067

Article  CAS  Google Scholar 

Huang, L., El-Hussein, A., Xuan, W., & Hamblin, M. R. (2018). Potentiation by potassium iodide reveals that the anionic porphyrin TPPS4 is a surprisingly effective photosensitizer for antimicrobial photodynamic inactivation. Journal of Photochemistry and Photobiology B, 178, 277–286. https://doi.org/10.1016/j.jphotobiol.2017.10.036

Article  CAS  Google Scholar 

Alves, E., Costa, L., Carvalho, C. M., Tomé, J. P., Faustino, M. A., Neves, M. G., Tomé, A. C., Cavaleiro, J. A., Cunha, Â., Almeida, A. (2009). Charge effect on the photoinactivation of Gram-negative and Gram-positive bacteria by cationic meso-substituted porphyrins. BMC Microbiology 9, 70.

Tavares, A., Dias, S. R. S., Carvalho, C. M. B., Faustino, M. A. F., Tomé, J. P. C., Neves, M. G. P. M. S., Tomé, A. C., Cavaleiro, J. A. S., Cunha, Â., Gomes, N. C. M., Alves, E., & Almeida, A. (2009). Mechanisms of photodynamic inactivation of a Gram-negative recombinant bioluminescent bacterium by cationic porphyrins. Photochemical & Photobiological Sciences 10, 1659–1669. https://doi.org/10.1039/c1pp05097d.

Du, Y., Liu, X., Wang, Q., Yu, L., Chu, L., & Sun, M. (2022). Metal free benzothiadiazole-diketopyrrolopyrrole-based conjugated polymer/g-C3N4 photocatalyst for enhanced sterilization and degradation in visible to near-infrared region. Journal of Colloid and Interface Science, 608, 103–113.

Comments (0)

No login
gif