New Porphyrin Functionalized with Azabicyclic Amidines for PDT Applications Carlos J. P. Monteiro a, Ana S. Joaquinitoa, Luca Menilli b, Federico Frendob, Giorgia Miolo b, Maria A. F. Faustinoa a LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. b Department of Pharmaceutical and Pharmacological Sciences, University of Padova, Via F. Marzolo 5, 35131 Padova, Italy. Photodynamic therapy (PDT) is a clinically established treatment based on the activation of a photosensitizer (PS) by visible light in the presence of dioxygen, leading to the generation of cytotoxic reactive oxygen species (ROS). [1,2]. Compared with conventional anticancer therapies, PDT offers several advantages, including minimal invasiveness, low systemic toxicity, selective cell destruction, good cosmetic outcomes, immune system stimulation, and high tolerability. Despite these benefits, the clinical impact of PDT remains constrained by the limited efficiency of available PSs, highlighting the need for more efficient PSs. Our research group has explored the synthetic versatility of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPFFP) as a multipurpose scaffold, enabling efficient and selective derivatization via nucleophilic aromatic substitution to generate libraries of biologically relevant photoactive compounds [3]. In this communication, we report new TPFFP derivatives functionalized with azabicyclic amidines, including their structural characterization, photophysical properties, and photodynamic activity against the MDA-MB-468 cell line. Acknowledgements/Funding :Financial support from the University of Aveiro and FCT, under the scope of project UID/50006/2025 of the Associate Laboratory for Green Chemistry - LAQV REQUIMTE and the Portuguese NMR Network. CJP Monteiro thanks FCT for funding through program Individual Call to Scientific Employment Stimulus (CEECIND-6th edition) https://doi.org/10.54499/2023.05956.CEECIND/CP2840/CT0005 . REFERENCES 1. Hamblin, M.R. Photochem. Photobiol. 2020, 96, 506-516. 2. Mesquita, M.Q.; Dias, C.J.; Neves, M.; Almeida, A.; Faustino, M.A.F. Molecules 2018, 23(10):2424. 3. Costa, J. I. T.; Tomé, A. C.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. J. Porphyrins Phthalocyanines 2011, 15 (11-12), 1116-1133. ORALS Kyoto, Japan - June 28 - July 3, 2026 - www.icpp-spp.org Copyright © 2026 Society of Porphyrins & Phthalocyanine
New Porphyrin Functionalized with Azabicyclic Amidines for PDT Applications
Luca Menilli;Giorgia Miolo;
2026
Abstract
New Porphyrin Functionalized with Azabicyclic Amidines for PDT Applications Carlos J. P. Monteiro a, Ana S. Joaquinitoa, Luca Menilli b, Federico Frendob, Giorgia Miolo b, Maria A. F. Faustinoa a LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. b Department of Pharmaceutical and Pharmacological Sciences, University of Padova, Via F. Marzolo 5, 35131 Padova, Italy. Photodynamic therapy (PDT) is a clinically established treatment based on the activation of a photosensitizer (PS) by visible light in the presence of dioxygen, leading to the generation of cytotoxic reactive oxygen species (ROS). [1,2]. Compared with conventional anticancer therapies, PDT offers several advantages, including minimal invasiveness, low systemic toxicity, selective cell destruction, good cosmetic outcomes, immune system stimulation, and high tolerability. Despite these benefits, the clinical impact of PDT remains constrained by the limited efficiency of available PSs, highlighting the need for more efficient PSs. Our research group has explored the synthetic versatility of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPFFP) as a multipurpose scaffold, enabling efficient and selective derivatization via nucleophilic aromatic substitution to generate libraries of biologically relevant photoactive compounds [3]. In this communication, we report new TPFFP derivatives functionalized with azabicyclic amidines, including their structural characterization, photophysical properties, and photodynamic activity against the MDA-MB-468 cell line. Acknowledgements/Funding :Financial support from the University of Aveiro and FCT, under the scope of project UID/50006/2025 of the Associate Laboratory for Green Chemistry - LAQV REQUIMTE and the Portuguese NMR Network. CJP Monteiro thanks FCT for funding through program Individual Call to Scientific Employment Stimulus (CEECIND-6th edition) https://doi.org/10.54499/2023.05956.CEECIND/CP2840/CT0005 . REFERENCES 1. Hamblin, M.R. Photochem. Photobiol. 2020, 96, 506-516. 2. Mesquita, M.Q.; Dias, C.J.; Neves, M.; Almeida, A.; Faustino, M.A.F. Molecules 2018, 23(10):2424. 3. Costa, J. I. T.; Tomé, A. C.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. J. Porphyrins Phthalocyanines 2011, 15 (11-12), 1116-1133. ORALS Kyoto, Japan - June 28 - July 3, 2026 - www.icpp-spp.org Copyright © 2026 Society of Porphyrins & Phthalocyanine
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