Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro

Ahmed, Sajida; Davoust, Eric; Savoie, H.; Boa, Andrew N; Boyle, Ross W

doi:10.1016/j.tetlet.2004.06.021

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.

PET/PDT theranostics: Synthesis and biological evaluation of a peptide-targeted gallium porphyrin (2015)
Journal Article
Bryden, F., Savoie, H., Rosca, E. V., & Boyle, R. W. (2015). PET/PDT theranostics: Synthesis and biological evaluation of a peptide-targeted gallium porphyrin. Dalton Transactions : an international journal of inorganic chemistry, 44(11), 4925-4932. https://doi.org/10.1039/c4dt02949f

The development of novel theranostic agents is an important step in the pathway towards personalised medicine, with the combination of diagnostic and therapeutic modalities into a single treatment agent naturally lending itself to the optimisation an... Read More about PET/PDT theranostics: Synthesis and biological evaluation of a peptide-targeted gallium porphyrin.

Conjugatable water-soluble Pt(ii) and Pd(ii) porphyrin complexes: Novel nano- and molecular probes for optical oxygen tension measurement in tissue engineering (2014)
Journal Article
Giuntini, F., Chauhan, V. M., Aylott, J. W., Rosser, G. A., Athanasiadis, A., Beeby, A., …Boyle, R. W. (2014). Conjugatable water-soluble Pt(ii) and Pd(ii) porphyrin complexes: Novel nano- and molecular probes for optical oxygen tension measurement in tissue engineering. Photochemical & photobiological sciences : an international journal, 13(7), 1039-1051. https://doi.org/10.1039/c4pp00026a

Measurement of oxygen tension in compressed collagen sheets was performed using matrix-embedded optical oxygen sensors based on platinum(II) and palladium(II) porphyrins supported on polyacrylamide nanoparticles. Bespoke, fully water-soluble, mono-fu... Read More about Conjugatable water-soluble Pt(ii) and Pd(ii) porphyrin complexes: Novel nano- and molecular probes for optical oxygen tension measurement in tissue engineering.

Regioselective and stoichiometrically controlled conjugation of photodynamic sensitizers to a HER2 targeting antibody fragment (2014)
Journal Article
Bryden, F., Maruani, A., Savoie, H., Chudasama, V., Smith, M. E. B., Caddick, S., & Boyle, R. W. (2014). Regioselective and stoichiometrically controlled conjugation of photodynamic sensitizers to a HER2 targeting antibody fragment. Bioconjugate chemistry, 25(3), 611-617. https://doi.org/10.1021/bc5000324

The rapidly increasing interest in the synthesis of antibody–drug conjugates as powerful targeted anticancer agents demonstrates the growing appreciation of the power of antibodies and antibody fragments as highly selective targeting moieties. This t... Read More about Regioselective and stoichiometrically controlled conjugation of photodynamic sensitizers to a HER2 targeting antibody fragment.

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.

A novel Bodipy-Dipyrrin fluorescent probe: Synthesis and recognition behaviour towards Fe (II) and Zn (II) (2012)
Journal Article
Kursunlu, A. N., Guler, E., Ucan, H. I., & Boyle, R. W. (2012). A novel Bodipy-Dipyrrin fluorescent probe: Synthesis and recognition behaviour towards Fe (II) and Zn (II). Dyes and pigments : an international journal, 94(3), 496-502. https://doi.org/10.1016/j.dyepig.2012.02.006

We present the design, synthesis, characterization and spectral studies for a new Zn (II) and Fe (II) selective fluorescent probe, 4,4-Difluoro-8-{3-[(4-phenoxy-dipyrromethene)propoxy]}-4-bora-3a,4a-diazaindacene (DPYBODPY). DPBODPY consists of a ter... Read More about A novel Bodipy-Dipyrrin fluorescent probe: Synthesis and recognition behaviour towards Fe (II) and Zn (II).

Orthogonally bifunctionalised polyacrylamide nanoparticles: a support for the assembly of multifunctional nanodevices (2012)
Journal Article
Giuntini, F., Dumoulin, F., Daly, R., Ahsen, V., Scanlan, E. M., Lavado, A. S. P., …Boyle, R. W. (2012). Orthogonally bifunctionalised polyacrylamide nanoparticles: a support for the assembly of multifunctional nanodevices. Nanoscale, 4(6), 2034-2045. https://doi.org/10.1039/c2nr11947a

Polyacrylamide nanoparticles bearing two orthogonal reactive functionalities were prepared by reverse microemulsion polymerisation. Water-soluble photosensitisers and peptide or carbohydrate moieties were sequentially attached to the new nanospecies... Read More about Orthogonally bifunctionalised polyacrylamide nanoparticles: a support for the assembly of multifunctional nanodevices.

Helimeric porphyrinoids: Stereostructure and chiral resolution of meso -tetraarylmorpholinochlorins (2011)
Journal Article
Brückner, C., Götz, D. C. G., Fox, S. P., Ryppa, C., McCarthy, J. R., Bruhn, T., …Bringmann, G. (2011). Helimeric porphyrinoids: Stereostructure and chiral resolution of meso -tetraarylmorpholinochlorins. Journal of the American Chemical Society, 133(22), 8740-8752. https://doi.org/10.1021/ja202451t

The synthesis and chiral resolution of free-base and Ni(II) complexes of a number of derivatives of meso-tetraphenylmorpholinochlorins, with and without direct β-carbon-to-o-phenyl linkages to the flanking phenyl groups, is described. The morpholinoc... Read More about Helimeric porphyrinoids: Stereostructure and chiral resolution of meso -tetraarylmorpholinochlorins.

Addressing fluorescence and liquid crystal behaviour in multi-mesogenic BODIPY materials (2011)
Journal Article
Benstead, M., Rosser, G. A., Beeby, A., Mehl, G. H., & Boyle, R. W. (2011). Addressing fluorescence and liquid crystal behaviour in multi-mesogenic BODIPY materials. New journal of chemistry = Nouveau journal de chimie, 35(7), 1410-1417. https://doi.org/10.1039/c0nj00990c

Two series of BODIPYs (4,4'-difluoro-3a, 4a-diaza-s-indacene) bearing mesogenic substituents have been synthesised and their fluorescent and self-assembly behaviour has been observed and characterised. In order to induce a strong preference for liqui... Read More about Addressing fluorescence and liquid crystal behaviour in multi-mesogenic BODIPY materials.

4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials (2011)
Journal Article
Benstead, M., Mehl, G. H., & Boyle, R. W. (2011). 4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials. Tetrahedron, 67(20), 3573-3601. https://doi.org/10.1016/j.tet.2011.03.028

Applications of BODIPY fluorophores as components of light active materials are reviewed.

Polyacrylamide nanoparticles as a delivery system in photodynamic therapy (2011)
Journal Article
Kuruppuarachchi, M., Lowry, A., Savoie, H., Alonso, C., & Boyle, R. W. (2011). Polyacrylamide nanoparticles as a delivery system in photodynamic therapy. Molecular pharmaceutics, 8(3), 920-931. https://doi.org/10.1021/mp200023y

Nanoparticles can be targeted towards, and accumulate in, tumor tissue by the enhanced permeability and retention effect, if sequestration by the reticuloendothelial system (RES) is avoided. The application of nanoparticles in the field of drug deliv... Read More about Polyacrylamide nanoparticles as a delivery system in photodynamic therapy.

A chemically modified antibody mediates complete eradication of tumours by selective disruption of tumour blood vessels (2011)
Journal Article
Palumbo, A., Hauler, F., Dziunycz, P., Schwager, K., Soltermann, A., Pretto, F., …Neri, D. (2011). A chemically modified antibody mediates complete eradication of tumours by selective disruption of tumour blood vessels. The British Journal of Cancer, 104(7), 1106-1115. https://doi.org/10.1038/bjc.2011.78

Background:The possibility of eradicating cancer by selective destruction of tumour blood vessels may represent an attractive therapeutic avenue, but most pharmaceutical agents investigated so far did not achieve complete cures and are not completely... Read More about A chemically modified antibody mediates complete eradication of tumours by selective disruption of tumour blood vessels.

Mesogenic BODIPYs: An investigation of the correlation between liquid crystalline behaviour and fluorescence intensity (2011)
Journal Article
Benstead, M., Beeby, A., Rosser, G. A., Mehl, G. H., & Boyle, R. W. (2011). Mesogenic BODIPYs: An investigation of the correlation between liquid crystalline behaviour and fluorescence intensity. Photochemical & photobiological sciences : an international journal, 10(6), 992-999. https://doi.org/10.1039/c0pp00388c

A series of mesogenic molecules based on the 4,4¢-di?uoro-3a,4a-diaza-s-indacene (BODIPY) ?uorophore have been synthesised and characterised. Each compound consists of one mesogenic unit, based on a cyanobiphenyl core, and one ?uorophore, of varying... Read More about Mesogenic BODIPYs: An investigation of the correlation between liquid crystalline behaviour and fluorescence intensity.

A set of highly water-soluble tetraethyleneglycol-substituted Zn(ii) phthalocyanines: synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity (2010)
Journal Article
Tuncel, S., Dumoulin, F., Gailer, J., Sooriyaarachchi, M., Atilla, D., Durmuş, M., …Ahsen, V. (2011). A set of highly water-soluble tetraethyleneglycol-substituted Zn(ii) phthalocyanines: synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity. Dalton Transactions : an international journal of inorganic chemistry, 40(16), 4067-4079. https://doi.org/10.1039/c0dt01260b

Three Zn(II) phthalocyanines substituted by hydroxyl-terminated tetraethylene glycol chains have been synthesized. In order to evaluate the potential of these highly water-soluble phthalocyanines as type II-photosensitisers for photodynamic therapy,... Read More about A set of highly water-soluble tetraethyleneglycol-substituted Zn(ii) phthalocyanines: synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity.

Porphyrin-nanosensor conjugates. New tools for the measurement of intracellular response to reactive oxygen species (2010)
Journal Article
Josefsen, L. B., Aylott, J. W., Beeby, A., Warburton, P., Boyle, J. P., Peers, C., & Boyle, R. W. (2010). Porphyrin-nanosensor conjugates. New tools for the measurement of intracellular response to reactive oxygen species. Photochemical & photobiological sciences : an international journal, 9(6), 801-811. https://doi.org/10.1039/c0pp00004c

Reactive oxygen species (ROS) have for some time been implicated in the onset and progression of medical conditions including cancer, ageing, heart disease and Alzheimer's disease. Recently, it has been postulated that ROS play a much more subtle rol... Read More about Porphyrin-nanosensor conjugates. New tools for the measurement of intracellular response to reactive oxygen species.

Site-specific and stoichiometric conjugation of cationic porphyrins to antiangiogenic monoclonal antibodies (2010)
Journal Article
Alonso, C. M. A., Palumbo, A., Bullous, A. J., Pretto, F., Neri, D., & Boyle, R. W. (2010). Site-specific and stoichiometric conjugation of cationic porphyrins to antiangiogenic monoclonal antibodies. Bioconjugate chemistry, 21(2), 302-313. https://doi.org/10.1021/bc9003537

Synthesis of three new cationic thiol-reactive maleimide-porphyrin derivatives and their use in site-specific conjugation to monoclonal antibodies is reported. The selective reactivity toward thiols is demonstrated using competition experiments, wher... Read More about Site-specific and stoichiometric conjugation of cationic porphyrins to antiangiogenic monoclonal antibodies.

Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity (2009)
Journal Article
Zorlu, Y., Ermeydan, M. A., Dumoulin, F., Ahsen, V., Savoie, H., & Boyle, R. W. (2009). Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity. Photochemical & photobiological sciences : an international journal, 8(3), 312-318. https://doi.org/10.1039/b817348f

Three novel water soluble, non-ionic, zinc phthalocyanines (Pcs) have been synthesized and their spectroscopic and photodynamic properties investigated in aqueous media. One of the three compounds was shown to be significantly less aggregated, when c... Read More about Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity.

Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins (2009)
Journal Article
Welch, C., Archibald, S. J., & Boyle, R. (2009). Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins. SYNTHESIS, 2009(4), 551-556. https://doi.org/10.1055/s-0028-1083335

Formylation followed by reductive amination of 5,10,15,20-tetraphenyl porphyrin (TPP) is shown to be a versatile synthetic procedure for monosubstitution of the porphyrin core re-giospecifically at one β-position. A diverse range of substituents can... Read More about Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins.

Mesogenic dipyrrins - building blocks for the fabrication of fluorescent and metal-containing materials (2008)
Journal Article
Wilson, C. J., James, L., Mehl, G. H., & Boyle, R. W. (2008). Mesogenic dipyrrins - building blocks for the fabrication of fluorescent and metal-containing materials. Chemical communications : Chem comm / the Royal Society of Chemistry, 4582-4584. https://doi.org/10.1039/b806672h

A new class of mesogenic dipyrrins is reported and their use in the fabrication of fluorescent and metal-containing self assembling materials is demonstrated.

Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro (2004)
Journal Article
Ahmed, S., Davoust, E., Savoie, H., Boa, A. N., & Boyle, R. W. (2004). Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 45(31), 6045-6047. https://doi.org/10.1016/j.tetlet.2004.06.021

A convenient and flexible synthesis of meso-tetraaryl porphyrins substituted with three thioglycosyl units, and also bearing one pyridyl substituent is reported. Quaternisation of the pyridine nitrogen with alkyl iodides gives access to a range of wa... Read More about Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro.

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