Carbohydrate substituted porphyrins. synthesis, characterization and lipoprotein binding properties

Hombrecher, Hermann K.; Schell, Christian

doi:10.1016/s0144-8617(97)87339-0

Cited by 3 publications

(2 citation statements)

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“…Liposomes and nanoparticles are a means to circumvent solubility problems, and many new compounds under investigation are amphipathic or hydrophobic, but selectivity remains an issue (17). A cadre of glycosylated porphyrins has been reported in recent years (18)(19)(20)(21)(22)(23) because of the advantages of appending cellular recognition elements to a drug, yet hydrolysis of the sugars from the O-glycosidic porphyrin derivatives remains problematicsboth in vivo and during synthesis/purification (24). Drugs bearing saccharides appended via O-glycoside linkages generally have short half-lives because this bond is readily hydrolyzed by a variety of enzymatic and nonenzymatic acid/base reactions.…”

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confidence: 99%

Efficient Synthesis and Photodynamic Activity of Porphyrin-Saccharide Conjugates: Targeting and Incapacitating Cancer Cells

et al. 2004

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Since the role of saccharides in cell recognition, metabolism, and cell labeling is well-established, the conjugation of saccharides to drugs is an active area of research. Thus, one goal in the use of saccharide-drug conjugates is to impart a greater specificity toward a given cell type or other targets. Although widely used to treat some cancers and age related macular degeneration, the drugs used in photodynamic therapy (PDT) display poor chemical selectivity toward the intended targets, and uptake by cells most likely arises from passive, diffusional processes. Instead, the specific irradiation of the target tissues, and the formation of the toxic species in situ, are the primary factors that modulate the selectivity in the present mode of PDT. We report herein a two-step method to make nonhydrolyzable saccharide-porphyrin conjugates in high yields using a tetra(pentafluorophenyl)porphyrin and the thio derivative of the sugar. As a demonstration of their properties, the selective uptake (and/or binding) of these compounds to several cancer cell types was examined, followed by an investigation of their photodynamic properties. As expected, different malignant cell types take up one type of saccharide-porphyrin conjugate preferentially over others; for example, human breast cancer cells (MDA-MB-231) absorb a tetraglucose-porphyrin conjugate over the corresponding galactose derivative. Doseametric studies reveal that these saccharide-porphyrin conjugates exhibit varying PDT responses depending on drug concentration and irradiation energy. (1) Using 20 microM conjugate and greater irradiation energy induces cell death by necrosis. (2) When 10-20 microM conjugate and less irradiation energy are used, both necrosis and apoptosis are observed. (3) Using 10 microM and the least irradiation energy, a significant reduction in cell migration is observed, which indicates a reduction in aggressiveness of the cancer cells.

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confidence: 99%

Efficient Synthesis and Photodynamic Activity of Porphyrin-Saccharide Conjugates: Targeting and Incapacitating Cancer Cells

et al. 2004

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“…PSs have been shown to bind to several plasma proteins depending on their amphiphilicity [377] . The more hydrophobic PSs bind to lipoproteins [378] while hydrophilic PSs bind to albumin [379] .…”

Section: Membrane and Protein 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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