Synthesis and investigation of glycosylated mono- and diarylporphyrins for photodynamic therapy

Schell, Christian; Hombrecher, Hermann K.

doi:10.1016/s0968-0896(99)00133-9

Cited by 12 publications

(9 citation statements)

References 28 publications

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“…Traditional approaches to achieve water solubility of porphyrins have largely relied on uroporphyrin (1)(2)(3)(4)(5), meso-tetrakis [4-(N-methyl)-pyridinium]porphyrin (6), and meso-tetrakis(4-sulfophenyl)-porphyrin (6) (Chart 1). More recent approaches have entailed attachment of the following motifs to the porphyrin via a meso-aryl group: oligo(ethylene glycol) (OEG) chains (7,8), OEG dendrimers (9), glycosyl units (10), alkyl polyamine chains (11), branched polycarboxy units (12), or malonate groups (13). Solubilizing groups that do not incorporate an aryl group include 1,2-dihydroxyethyl at the porphyrin meso position (14) and a variety of substituents attached to the β-position of a sapphyrin (15).…”

Section: Introductionmentioning

confidence: 99%

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

et al. 2006

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A broad range of applications requires access to water-soluble, bioconjugatable porphyrins. Branched alkyl groups attached at the branching site to the porphyrin meso position are known to impart high organic solubility. Such "swallowtail" motifs bearing a polar group (hydroxy, dihydroxyphosphoryl, dihydroxyphosphoryloxy) at the terminus of each branch have now been incorporated at a meso site in trans-AB-porphyrins. The incorporation of the swallowtail motif relies on rational synthetic methods whereby a 1,9-bis(N-propylimino)dipyrromethane (bearing a bioconjugatable tether at the 5-position) is condensed with a dipyrromethane (bearing a protected 1,5-dihydroxypent-3-yl unit at the 5-position). The two hydroxy groups in the swallowtail motif of each of the resulting zinc porphyrins can be transformed to the corresponding diphosphate or diphosphonate product. A 4-(carboxymethyloxy)phenyl group provides the bioconjugatable tether. The six such porphyrins reported here are highly water-soluble (≥20 mM at room temperature in water at pH 7) as determined by visual inspection, UV-vis absorption spectroscopy, or 1 H NMR spectroscopy. Covalent attachment was carried out in aqueous solution with the unprotected porphyrin diphosphonate and a monoclonal antibody against the T-cell receptor CD3ε. The resulting conjugate performed comparably to a commercially available fluorescein isothiocyanatelabeled antibody with Jurkat cells in flow cytometry and fluorescence microscopy assays. Taken together, this work enables preparation of useful quantities of water-soluble, bioconjugatable porphyrins in a compact architecture for applications in the life sciences.

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Section: Introductionmentioning

confidence: 99%

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

et al. 2006

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“…This low yield is explained by parallel reactions leading to the corresponding undesired monoporphyrin, 2,8,13,17-tetraethyl-3,7,12,18-tetramethylporphyrin. 49 Several attempts were made to increase the yield but without success. The complexation of zinc(II) proceeds quantitatively using zinc(II) acetate, and the corresponding biszinc(II) complex (5) is obtained.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Photophysical Properties of a Free Base and a Biszinc(II) Complex of 1,3-Bisporphyrincalix[4]arene: Evidence for “Tunable Intramolecular Open and Closed Conformations”

et al. 2005

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The bismacrocycle 5,17-bis[5-(2,8,13,17-tetraethyl-3,7,12,18-tetramethylporphyrinyl)]-25,26,27,28-tetrapropoxycalix[4]arene (4) was synthesized in three steps from the corresponding bisaldehyde 5,17-diformyl-25,26,27,28-tetrapropoxycalix[4]arene. The biszinc(II) complex (5) was prepared as well, and the photophysical properties were measured using 2-MeTHF as solvent at 298 and 77 K. While computer modeling for 5 predicts that both pinched cone conformers, closed (porphyrins near each other) and open (porphyrins away from each other), may exist in the "gas phase", the experimental data indicate clearly that no zinc porphyrin...zinc porphyrin interactions are present in solution at 298 K, favoring the open conformer, where the two macrocycles are placed away from each other. On the other hand, clear evidence for a closed conformer is observed at 77 K. Variable-temperature (1)H NMR experiments show that 5 is fluxional between 298 and 183 K, while 4 keeps the open conformation for the whole temperature range. This behavior is unprecedented for calix[4]areneporphyrin compounds, and the relative porphyrin ring rigidity is postulated to explain this difference.

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“…Such vesicles have been observed under electron microscopes to be 100-150 nm in diameter [62] . Initial work on porphyrin conjugates focused on steroids [68,69] . For example, the first investigation was aimed at studying the effect of steroid hormones such as estrone and progesterone for targeting an excess of receptors in breast cancer cells [70] .…”

Section: Porphyrin Bioconjugatesmentioning

confidence: 99%

“…The porphyrin 402 was prepared in 5 % yield using a mixed 2+2 condensation of a sugar-and steroid dipyrromethane [68] . The porphyrin was easily incorporated into phosphatidyl ethanolamine vesicles and formed vesicles or aggregates in water [69] . The first ever porphyrin-carbohydrate bioconjugate synthesized for a specific medicinal application remains to date one of the most complex and elaborate systems.…”

Section: Dual Modality Systemsmentioning

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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Synthesis and investigation of glycosylated mono- and diarylporphyrins for photodynamic therapy

Cited by 12 publications

References 28 publications

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

Synthesis, Characterization, and Photophysical Properties of a Free Base and a Biszinc(II) Complex of 1,3-Bisporphyrincalix[4]arene: Evidence for “Tunable Intramolecular Open and Closed Conformations”

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

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