Porphyrin–bile acid conjugates: from saccharide recognition in the solution to the selective cancer cell fluorescence detection

Králová, Jarmila; Koivukorpi, Juha; Kejík, Zdeněk; Poučková, P; Sievänen, Elina; Kolehmainen, Erkki; Král, Vladimír

doi:10.1039/b717528k

Cited by 50 publications

(29 citation statements)

References 33 publications

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“…44 On the basis of the results from previous work by Král and coworkers, the Kalenius group used bile acid-a steroid derivative-as the porphyrin appendage with the goal of effecting saccharide-specific molecular recognition. 48 The attachment of two bile acid arms to a porphyrin core creates a host, 17-a system expected to be capable of not only hydrogen bonding but also stabilizing hydrophobic and hydrophilic interactions ( Figure 17). MS analyses revealed 1 : 1 complexation between 17 and Glc 4 and provided support for this particular receptor being selective for oligosaccharides comprising at least three glucose residues.…”

Section: Saccharidesmentioning

confidence: 99%

Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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This chapter summarizes recent efforts to use porphyrins and expanded porphyrins as receptors. These unique macrocycles bear resemblance to naturally occurring tetrapyrrolic pigments and have been studied extensively as building blocks for a variety of functional molecular receptors. The introduction discusses the inherent characteristics of porphyrins and their analogs from the perspective of receptor design and is designed to highlight key features. These features include ease of synthesis and functionalization, the hydrogen‐bonding ability of the constituent pyrrolic NH protons, and the fact that the systems in question are often highly colored. This latter feature has afforded an extremely useful means of analyzing host–guest interactions. Because of space limitations, not all of the literature on this topic could be covered in a comprehensive manner. The definition of “receptor” is also limited to species that are thought to be operated via strictly noncovalent‐ or supramolecular‐type interactions. However, this definition is expanded in a few special cases. The goal of this article is not to cite every published article on this topic, but to highlight interesting examples of porphyrin and expanded porphyrins and their utility as receptors. An effort has also been made to describe the analytical techniques used to characterize the resulting host–guest ensembles. This chapter is organized according to the type of guest. One section covers the relatively new area of supramolecular π–π interactions involving porphyrins and nanomaterials, such as fullerenes and nanotubes. Another section discusses porphyrins as receptors for biological entities, including saccharides, peptides, and proteins, as well as DNA. The next section covers porphyrins and expanded porphyrins as anion receptors. This latter treatment includes a discussion of supramolecular electron‐transfer dyads. The use of porphyrins in sensing applications is also presented in summary form. Finally, a perspective on this rapidly growing field of supramolecular chemistry is included in the final remarks. It is hoped that the combination of cited references and listed further readings will allow the interested reader to learn more about this fast‐evolving and fascinating topic.

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Section: Saccharidesmentioning

confidence: 99%

Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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“…91 They showed good PDT activity in in vitro studies with A431NS, HeLaS3, 4T1 and FHC cell lines and ablated tumors in BALB/c mice which were subcutaneously transplanted with 4T1 mammary carcinoma cells. 92 Binding studies showed that these compounds have the potential to recognize various oligosaccharides under physiological conditions and can be used for selective fluorescence detection of transformed cells expressing glycosylated markers.…”

Section: Porphyrin-bile Acid Conjugatesmentioning

confidence: 99%

Current Developments in Using MESO-(TETRA) Substituted Porphyrins for PDT

Shaker¹,

Sweed²,

Moylan³

et al. 2016

Handbook of Photodynamic Therapy

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“…Picket fence type αααα-TPP's containing urea, carbamate, or amide groups provided carbohydrate recognition through hydrogen-bonding and CH-π interactions [127,128] . Several studies have been carried out using bile acid conjugate porphyrins for carbohydrate recognition [129][130][131] , one particular example exhibits the potential of such derivatives for direct targeting of bile acid porphyrins to sugar moieties which are expressed on malignant tumors. Both in vivo and in vitro studies displayed significant potential for PDT [129] .…”

Section: Porphyrin Carbohydrate Interactionsmentioning

confidence: 99%

“…Several studies have been carried out using bile acid conjugate porphyrins for carbohydrate recognition [129][130][131] , one particular example exhibits the potential of such derivatives for direct targeting of bile acid porphyrins to sugar moieties which are expressed on malignant tumors. Both in vivo and in vitro studies displayed significant potential for PDT [129] . Likewise, positively charged amphiphilic cyclodextrins were investigated as supramolecular aggregates for the delivery of PSs to bacterial cells for antimicrobial PDT.…”

Section: Porphyrin Carbohydrate Interactionsmentioning

confidence: 99%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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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.

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Porphyrin–bile acid conjugates: from saccharide recognition in the solution to the selective cancer cell fluorescence detection

Cited by 50 publications

References 33 publications

Porphyrins and Expanded Porphyrins as Receptors

Porphyrins and Expanded Porphyrins as Receptors

Current Developments in Using MESO-(TETRA) Substituted Porphyrins for PDT

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

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