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Synthesis of a porphyrin with histidine-like chelate: an efficient path towards molecular PDT/SPECT theranostics (2020)
Journal Article
Yap, S. Y., Savoie, H., Renard, I., Burke, B. P., Sample, H. C., Michue-Seijas, S., …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

© 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 chel... Read More about Synthesis of a porphyrin with histidine-like chelate: an efficient path towards molecular PDT/SPECT theranostics.

Homo‐ and heterodinuclear arene‐linked osmium(II) and ruthenium(II) organometallics: probing the impact of metal variation on reactivity and biological activity (2020)
Journal Article
Wilson, C. S., Prior, T. J., Sandland, J., Savoie, H., Boyle, R. W., & Murray, B. S. (in press). Homo‐ and heterodinuclear arene‐linked osmium(II) and ruthenium(II) organometallics: probing the impact of metal variation on reactivity and biological activity. Chemistry: a European journal, https://doi.org/10.1002/chem.202002052

Dinuclear metallodrugs offer much potential in the development of novel anticancer chemotherapeutics as a result of the distinct interactions possible with biomacromolecular targets and the unique biological activity that can result. Here, we describ... Read More about Homo‐ and heterodinuclear arene‐linked osmium(II) and ruthenium(II) organometallics: probing the impact of metal variation on reactivity and biological activity.

Synthesis and in Vitro Biological Evaluation of a Second-Generation Multimodal Water-Soluble Porphyrin-RAPTA Conjugate for the Dual-Therapy of Cancers (2020)
Journal Article
Sandland, J., Savoie, H., Boyle, R. W., & Murray, B. S. (2020). Synthesis and in Vitro Biological Evaluation of a Second-Generation Multimodal Water-Soluble Porphyrin-RAPTA Conjugate for the Dual-Therapy of Cancers. Inorganic chemistry, 59(11), 7884-7893. https://doi.org/10.1021/acs.inorgchem.0c01044

In this study, we report the synthesis and biological evaluation of a novel cationic porphyrin-[Ru(η6-arene)(C2O4)PTA] (RAPTA) conjugate with potential as a multimodal dual-therapeutic agent. In the absence of high intensity light, relative to untrea... Read More about Synthesis and in Vitro Biological Evaluation of a Second-Generation Multimodal Water-Soluble Porphyrin-RAPTA Conjugate for the Dual-Therapy of Cancers.

Evaluation of a bispidine‐based chelator for gallium‐68 and of the porphyrin conjugate as PET/PDT theranostic agent (2020)
Journal Article
Price, T., Yap, S. Y., Gillet, R., Savoie, H., Charbonnière, L. J., Boyle, R. W., …Stasiuk, G. J. (2020). Evaluation of a bispidine‐based chelator for gallium‐68 and of the porphyrin conjugate as PET/PDT theranostic agent. Chemistry: a European journal, 26(34), 7602-7608. https://doi.org/10.1002/chem.201905776

In this study a bispidine ligand has been applied to the complexation of gallium(III) and radiolabelled with gallium-68 for the first time. Despite its 5-coordinate nature, the resulting complex is stable in serum for over two hours, demonstrating a... Read More about Evaluation of a bispidine‐based chelator for gallium‐68 and of the porphyrin conjugate as PET/PDT theranostic agent.

The Application of Reversible Intramolecular Sulfonamide Ligation to Modulate Reactivity in Organometallic Ruthenium(II) Diamine Complexes (2020)
Journal Article
Kemp, S. A., Prior, T. J., Savoie, H., Boyle, R. W., & Murray, B. S. (2020). The Application of Reversible Intramolecular Sulfonamide Ligation to Modulate Reactivity in Organometallic Ruthenium(II) Diamine Complexes. Molecules, 25(2), 244. https://doi.org/10.3390/molecules25020244

Metallation of biomacromolecular species forms the basis for the anticancer activity of many metallodrugs. A major limitation of these compounds is that their reactivity is indiscriminate and can, in principle, occur in healthy tissue as well as canc... Read More about The Application of Reversible Intramolecular Sulfonamide Ligation to Modulate Reactivity in Organometallic Ruthenium(II) Diamine Complexes.

Selective radiolabelling with 68Ga under mild conditions: a route towards a porphyrin PET/PDT theranostic agent (2018)
Journal Article
Yap, S. Y., Price, T. W., Savoie, H., Boyle, R. W., & Stasiuk, G. J. (2018). Selective radiolabelling with 68Ga under mild conditions: a route towards a porphyrin PET/PDT theranostic agent. Chemical communications : Chem comm / the Royal Society of Chemistry, 54(57), 7952-7954. https://doi.org/10.1039/c8cc03897j

A theranostic conjugate for use as a positron emission tomography (PET) radiotracer and as a photosensitiser for photodynamic therapy (PDT) has been synthesised. A water-soluble porphyrin was coupled with the bifunctional chelate, H4Dpaa.ga. This con... Read More about Selective radiolabelling with 68Ga under mild conditions: a route towards a porphyrin PET/PDT theranostic agent.

Photo-induced anticancer activity and singlet oxygen production of prodigiosenes (2018)
Journal Article
Savoie, H., Figliola, C., Marchal, E., Crabbe, B. W., Hallett-Tapley, G. L., Boyle, R. W., & Thompson, A. (2018). Photo-induced anticancer activity and singlet oxygen production of prodigiosenes. Photochemical & photobiological sciences : an international journal, 17(5), 599-606. https://doi.org/10.1039/c8pp00060c

© 2018 The Royal Society of Chemistry and Owner Societies. The photo-induced cytotoxicity of prodigiosenes is reported. One prodigiosene represents a synthetic analogue of the natural product prodigiosin, and two are conjugated to molecules that targ... Read More about Photo-induced anticancer activity and singlet oxygen production of prodigiosenes.

Synthesis and Characterization of Temperature-Sensitive and Chemically Cross-Linked Poly(N-isopropylacrylamide)/Photosensitizer Hydrogels for Applications in Photodynamic Therapy (2018)
Journal Article
Belali, S., Savoie, H., O’Brien, J. M., Cafolla, A. A., O’Connell, B., Karimi, A. R., …Senge, M. O. (2018). Synthesis and Characterization of Temperature-Sensitive and Chemically Cross-Linked Poly(N-isopropylacrylamide)/Photosensitizer Hydrogels for Applications in Photodynamic Therapy. Biomacromolecules, 19(5), 1592-1601. https://doi.org/10.1021/acs.biomac.8b00293

Copyright © 2018 American Chemical Society. A novel poly(N-isopropylacrylamide) (PNIPAM) hydrogel containing different photosensitizers (protoporphyrin IX (PpIX), pheophorbide a (Pba), and protoporphyrin IX dimethyl ester (PpIX-DME)) has been synthes... Read More about Synthesis and Characterization of Temperature-Sensitive and Chemically Cross-Linked Poly(N-isopropylacrylamide)/Photosensitizer Hydrogels for Applications in Photodynamic Therapy.

pH-dependent modulation of reactivity in Ruthenium(II) organometallics (2018)
Journal Article
Prior, T. J., Savoie, H., Boyle, R. W., & Murray, B. S. (2018). pH-dependent modulation of reactivity in Ruthenium(II) organometallics. Organometallics, 37(3), 294-297. https://doi.org/10.1021/acs.organomet.7b00868

The pH-dependent intramolecular chelation of a tethered sulfonamide ligand in ruthenium(II) arene complexes is demonstrated, a process shown to modulate metal-centered reactivity toward the model ligand guanosine 5′-monophosphate within the physiolog... Read More about pH-dependent modulation of reactivity in Ruthenium(II) organometallics.

Synthesis of a novel HER2 targeted aza-BODIPY–antibody conjugate: synthesis, photophysical characterisation and in vitro evaluation (2018)
Journal Article
Cheng, M. H. Y., Cheng, M. H., Maruani, A., Savoie, H., Chudasama, V., & Boyle, R. W. (2018). Synthesis of a novel HER2 targeted aza-BODIPY–antibody conjugate: synthesis, photophysical characterisation and in vitro evaluation. Organic & biomolecular chemistry, 16(7), 1144-1149. https://doi.org/10.1039/c7ob02957h

We herein report the synthesis and analysis of a novel aza-BODIPY–antibody conjugate, formed by controlled and regioselective bioconjugation methodology. Employing the clinically relevant antibody, which targets HER2 positive cancers, represents the... Read More about Synthesis of a novel HER2 targeted aza-BODIPY–antibody conjugate: synthesis, photophysical characterisation and in vitro evaluation.

Assembly of high-potency photosensitizer-antibody conjugates through application of dendron multiplier technology (2017)
Journal Article
Rodrigues, J. M., Cheng, M. H., Bryden, F., Maruani, A., Rodrigues, J. M. M., Cheng, M. H. Y., …Boyle, R. W. (2018). Assembly of high-potency photosensitizer-antibody conjugates through application of dendron multiplier technology. Bioconjugate chemistry, 29(1), 176-181. https://doi.org/10.1021/acs.bioconjchem.7b00678

© 2017 American Chemical Society. Exploitation of photosensitizers as payloads for antibody-based anticancer therapeutics offers a novel alternative to the small pool of commonly utilized cytotoxins. However, existing bioconjugation methodologies are... Read More about Assembly of high-potency photosensitizer-antibody conjugates through application of dendron multiplier technology.

Generation of triplet excited states via photoinduced electron transfer in meso-anthra-BODIPY: fluorogenic response toward singlet oxygen in solution and in vitro (2017)
Journal Article
Filatov, M. A., Karuthedath, S., Polestshuk, P. M., Savoie, H., Flanagan, K. J., Sy, C., …Senge, M. O. (2017). Generation of triplet excited states via photoinduced electron transfer in meso-anthra-BODIPY: fluorogenic response toward singlet oxygen in solution and in vitro. Journal of the American Chemical Society, 139(18), 6282-6285. https://doi.org/10.1021/jacs.7b00551

© 2017 American Chemical Society. Heavy atom-free BODIPY-anthracene dyads (BADs) generate locally excited triplet states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequ... Read More about Generation of triplet excited states via photoinduced electron transfer in meso-anthra-BODIPY: fluorogenic response toward singlet oxygen in solution and in vitro.

NanoSOSG : a nanostructured fluorescent probe for detection of intracellular singlet oxygen (2017)
Journal Article
Ruiz-González, R., Gulías, Ò., Ruiz-González, R., Bresolí-Obach, R., Gulías, Ò., Agut, M., …Giuntini, F. (2017). NanoSOSG : a nanostructured fluorescent probe for detection of intracellular singlet oxygen. Angewandte Chemie, 56(11), 2885-2888. https://doi.org/10.1002/anie.201609050

A biocompatible fluorescent nanoprobe for singlet oxygen (¹O₂) detection in biological systems was designed, synthesized, and characterized, that circumvents many of the limitations of the molecular probe Singlet Oxygen Sensor Green® (SOSG). This wid... Read More about NanoSOSG : a nanostructured fluorescent probe for detection of intracellular singlet oxygen.

Synthesis, characterization and biological evaluation of a new photoactive hydrogel against Gram-positive and Gram-negative bacteria (2016)
Journal Article
Spagnul, C., Greenman, J., Wainwright, M., Kamil, Z., & Boyle, R. W. (2016). Synthesis, characterization and biological evaluation of a new photoactive hydrogel against Gram-positive and Gram-negative bacteria. Journal of Materials Chemistry B, 4(8), 1499-1509. https://doi.org/10.1039/c5tb02569a

© 2016 The Royal Society of Chemistry. In 2013, the World Health Organization reported that 884 million people lack access to clean potable water. Photodynamic antimicrobial chemotherapy (PACT) is a very promising alternative to conventional antibiot... Read More about Synthesis, characterization and biological evaluation of a new photoactive hydrogel against Gram-positive and Gram-negative bacteria.

Mechanisms of growth inhibition of primary prostate epithelial cells following gamma irradiation or photodynamic therapy including senscence, necrosis, and autophagy, but not apoptosis (2015)
Journal Article
Frame, F. M., Savoie, H., Bryden, F., Giuntini, F., Mann, V. M., Simms, M. S., …Maitland, N. J. (2016). Mechanisms of growth inhibition of primary prostate epithelial cells following gamma irradiation or photodynamic therapy including senscence, necrosis, and autophagy, but not apoptosis. Cancer medicine, 5(1), 61-73. https://doi.org/10.1002/cam4.553

In comparison to more differentiated cells, prostate cancer stem-like cells are radioresistant, which could explain radio-recurrent prostate cancer. Improvement of radiotherapeutic efficacy may therefore require combination therapy. We have investiga... Read More about Mechanisms of growth inhibition of primary prostate epithelial cells following gamma irradiation or photodynamic therapy including senscence, necrosis, and autophagy, but not apoptosis.

Development of PDT/PET theranostics: synthesis and biological evaluation of an ¹⁸F-radiolabeled water soluble porphyrin (2015)
Journal Article
Entract, G. M., Bryden, F., Domarkas, J., Savoie, H., Allott, L., Archibald, S. J., …Boyle, R. W. (2015). Development of PDT/PET theranostics: synthesis and biological evaluation of an ¹⁸F-radiolabeled water soluble porphyrin. Molecular pharmaceutics, 12(12), 4414-4423. https://doi.org/10.1021/acs.molpharmaceut.5b00606

Synthesis of the first water-soluble porphyrin radiolabeled with fluorine-18 is described: a new molecular theranostic agent which integrates the therapeutic selectivity of photodynamic therapy (PDT) with the imaging efficacy of positron emission tom... Read More about Development of PDT/PET theranostics: synthesis and biological evaluation of an ¹⁸F-radiolabeled water soluble porphyrin.

Site-selective multi-porphyrin attachment enables the formation of a next-generation antibody-based photodynamic therapeutic (2015)
Journal Article
Maruani, A., Savoie, H., Bryden, F., Caddick, S., Boyle, R., & Chudasama, V. (2015). Site-selective multi-porphyrin attachment enables the formation of a next-generation antibody-based photodynamic therapeutic. Chemical communications : Chem comm / the Royal Society of Chemistry, 51(83), 15304-15307. https://doi.org/10.1039/c5cc06985h

Herein we present a significant step towards next-generation antibody-based photodynamic therapeutics. Site-selective modification of a clinically relevant monoclonal antibody, with a serum-stable linker bearing a strained alkyne, allows for the cont... Read More about Site-selective multi-porphyrin attachment enables the formation of a next-generation antibody-based photodynamic therapeutic.

Controlled intracellular generation of reactive oxygen species in human mesenchymal stem cells using porphyrin conjugated nanoparticles (2015)
Journal Article
Lavado, A. S., Chauhan, V. M., Zen, A. A., Giuntini, F., Jones, D. R. E., Boyle, R. W., …Aylott, J. W. (2015). Controlled intracellular generation of reactive oxygen species in human mesenchymal stem cells using porphyrin conjugated nanoparticles. Nanoscale, 7(34), 14525-14531. https://doi.org/10.1039/c5nr00795j

Nanoparticles capable of generating controlled amounts of intracellular reactive oxygen species (ROS), that advance the study of oxidative stress and cellular communication, were synthesized by functionalizing polyacrylamide nanoparticles with zinc(I... Read More about Controlled intracellular generation of reactive oxygen species in human mesenchymal stem cells using porphyrin conjugated nanoparticles.

Immobilized photosensitizers for antimicrobial applications (2015)
Journal Article
Spagnul, C., Turner, L. C., & Boyle, R. W. (2015). Immobilized photosensitizers for antimicrobial applications. Journal of photochemistry and photobiology. B, Biology, 150(September), 11-30. https://doi.org/10.1016/j.jphotobiol.2015.04.021

Photodynamic antimicrobial chemotherapy (PACT) is a very promising alternative to conventional antibiotics for the efficient inactivation of pathogenic microorganisms; this is due to the fact that it is virtually impossible for resistant strains to d... Read More about Immobilized photosensitizers for antimicrobial applications.

Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: Towards mild strategies for the labelling of glycans (2014)
Journal Article
Giuntini, F., Bryden, F., Daly, R., Scanlan, E. M., & Boyle, R. W. (2014). Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: Towards mild strategies for the labelling of glycans. Organic & biomolecular chemistry, 12(8), 1203-1206. https://doi.org/10.1039/c3ob42306a

Fully deprotected alkynyl-functionalised mono- and oligosaccharides undergo CuAAC-based conjugation with water-soluble porphyrin azides in aqueous environments. The mild reaction conditions are fully compatible with the presence of labile glycosidic... Read More about Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: Towards mild strategies for the labelling of glycans.