Synthesis of a porphyrin with histidine-like chelate: an efficient path towards molecular PDT/SPECT theranostics

Yap, Steven Y.; Savoie, Huguette; Renard, Isaline; Burke, Benjamin P.; Sample, Harry C.; Michue-Seijas, Saul; Archibald, Stephen J.; Boyle, Ross W.; Stasiuk, Graeme J.

Abstract

© The Royal Society of Chemistry 2020. The goal of “personalised” medicine has seen a growing interest in the development of theranostic agents. Bifunctional, and targeted-trifunctional, theranostic water-soluble porphyrins with a histidine-like chelating group have been synthesisedviacopper-catalysed azide-alkyne cycloaddition (CuAAC) “click” chemistry in high yield and purity. They are capable of photodynamic treatment and [99mTc(CO)3]+complexation for single-photon emission computed tomography (SPECT) imaging, with a radiochemical yield of >95%. The toxicity and phototoxicity were evaluated on HT-29 cells, DU145, and DU145-PSMA cell lines, with the targeted theranostic showing more potent phototoxicity towards DU145-PSMA expressing cells.

Citation

Yap, S. Y., Savoie, H., Renard, I., Burke, B. P., Sample, H. C., Michue-Seijas, S., Archibald, S. J., Boyle, R. W., & Stasiuk, G. J. (2020). Synthesis of a porphyrin with histidine-like chelate: an efficient path towards molecular PDT/SPECT theranostics. Chemical communications : Chem comm / the Royal Society of Chemistry, 56(75), 11090-11093. https://doi.org/10.1039/d0cc03958f

• Journal Article Type: Article
• Acceptance Date: Aug 12, 2020
• Online Publication Date: Aug 12, 2020
• Publication Date: Sep 25, 2020
• Deposit Date: Nov 30, 2020
• Publicly Available Date: Nov 30, 2020
• Journal: Chemical Communications
• Print ISSN: 1359-7345
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 56
• Issue: 75
• Pages: 11090-11093
• DOI: https://doi.org/10.1039/d0cc03958f
• Keywords: Materials Chemistry; Electronic, Optical and Magnetic Materials; General Chemistry; Surfaces, Coatings and Films; Metals and Alloys; Ceramics and Composites; Catalysis
• Public URL: https://hull-repository.worktribe.com/output/3560008