Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: towards mild strategies for the labelling of glycans

Giuntini, Francesca; Bryden, Francesca; Daly, Robin M.; Scanlan, Eoin M.; Boyle, Ross W.

doi:10.1039/c3ob42306a

Cited by 27 publications

(33 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…None of the glycoporphyrins showed PDT efficacy under these experimental conditions. Similar results for triazole linked glycoporphyrins have been reported [251,324] , while no biological data are available for related cationic bioconjugates [347] . However, the D 2 -symmetric 5α,10β,15α,20β-tetrakis(1,2:3,4-di-Oisopropylidene-α-D-galactopyranose-6yl)porphyrin localized in lysosomes and caused cell death by apoptosis via caspasedependent apoptotic pathways [348] .…”

Section: Meso-substituted Porphyrinssupporting

confidence: 69%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

View full text Add to dashboard Cite

Abstract:This review presents an in-depth overview of the modification of porphyrins with bioconjugates and their applications in medicine today. Porphyrin bioconjugates ranging from nucleotides to steroids are under active scrutiny. However, carbohydrates have been at the forefront of such research in recent years and offer significant potential. This is attributed to their own selectivity to lectins on the surface of cancer cells and their influence on the amphiphilicity of the porphyrin macrocycle. These characteristics and the tendency of porphyrin photosensitizers to accumulate in tumor tissues make glycoporphyrins promising candidates for use as photosensitizers. Thus, a detailed overview of the synthesis and biological evaluation of glycoporphyrins is given with a particular focus on their applications in photodynamic therapy and their future prospects as drug candidates have been reported.

show abstract

Section: Meso-substituted Porphyrinssupporting

confidence: 69%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

View full text Add to dashboard Cite

show abstract

“…These porphyrins have previously been shown to exhibit potent cytotoxic action even when metallated with zinc, 18 and also undergo click reactions rapidly without the need for reaction intensification 17 , important for the rapid click conjugation of a thermally-sensitive peptide following radiolabelling. These porphyrins have previously been shown to exhibit potent cytotoxic action even when metallated with zinc, 18 and also undergo click reactions rapidly without the need for reaction intensification 17 , important for the rapid click conjugation of a thermally-sensitive peptide following radiolabelling.…”

Section: Synthesis Of 69/71 Ga Porphyrinsmentioning

confidence: 99%

“…It was therefore envisaged that the development of novel targeted theranostic agents could be achieved through the combination of the demonstrated radiolabelling potential of porphyrins with our current interest in the mild bio-orthogonal conjugation of porphyrin photosensitisers to targeting moieties [16][17][18] through use of the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC) reaction. This reaction is mild and generally high yielding 19,20 and has been shown to be highly compatible with both porphyrin bioconjugation and radiochemistry, being largely insensitive to steric hindrance and operating well in aqueous conditions without the need for high temperatures or long reaction times.…”

Section: Introductionmentioning

confidence: 99%

PET/PDT theranostics: synthesis and biological evaluation of a peptide-targeted gallium porphyrin

et al. 2015

Self Cite

View full text Add to dashboard Cite

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 and personalisation of treatment. In pursuit of the goal of a molecular theranostic suitable for use as a PET radiotracer and a photosensitiser for PDT, a novel radiolabelled peptide-porphyrin conjugate targeting the α6β1-integrin has been developed. (69/71)Ga and (68)Ga labelling of an azide-functionalised porphyrin has been carried out in excellent yields, with subsequent bioconjugation to an alkyne-functionalised peptide demonstrated. α6β1-integrin expression of two cell lines has been evaluated by flow cytometry, and therapeutic potential of the conjugate demonstrated. Evaluation of the phototoxicity of the porphyrin-peptide theranostic conjugate in comparison to an untargeted control porphyrin in vitro, demonstrated significantly enhanced activity for a cell line with higher α6β1-integrin expression when compared with a cell line exhibiting lower α6β1-integrin expression.

show abstract

“…In this report iron azido porphyrin 85 (Figure 36) [138] with a monosaccharide, a disaccharide and a trisaccharide.…”

Section: Mono Substituted Azido-phenyl Porphyrinsmentioning

confidence: 95%

“Click”-reaction: An alternative tool for new architectures of porphyrin based derivatives

Ladomenou

Nikolaou

Charalambidis

et al. 2016

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: towards mild strategies for the labelling of glycans

Cited by 27 publications

References 42 publications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

PET/PDT theranostics: synthesis and biological evaluation of a peptide-targeted gallium porphyrin

“Click”-reaction: An alternative tool for new architectures of porphyrin based derivatives

Contact Info

Product

Resources

About