Synthesis and investigation of a galactopyranosyl-cholesteryloxy substituted porphyrin

Hombrecher, Hermann K.; Schell, Christian; Thiem, Joachim

doi:10.1016/0960-894x(96)00201-6

Cited by 28 publications

(13 citation statements)

References 12 publications

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“…[15] These porphyrinic vesicles were characterized by strong exciton splitting of the Soret absorption band. [15] We therefore tried to stimulate a self-assembling process for the newly synthesized compounds 11 a ± g. The porphyrinic compounds 11 a ± g were added to a micellar solution of CHAPS in phosphate-buffered saline solution (PBS) at pH 7 and incubated for 24 hours. Then the surfactant was removed by dialysis and the dialysed solution was treated with ultrasound to promote the formation of self-assembling structures.…”

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confidence: 99%

Synthesis, Self-Assembling Properties and Incorporation of Carbohydrate-Substituted Porphyrins into Cell Membrane Models

Schell

Hombrecher

1999

Chem. Eur. J.

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A general and very efficient synthesis of new carbohydrate-substituted porphyrins is described. Reaction of porphyrin 6 with different glycosyl imidates 7 a ± g leads to the formation of carbohydrate-substituted porphyrins 9 a ± g in good yield. Subsequent demetallation and removal of the carbohydrate protection groups leads to the metal-free compounds 11 a ± g. In aqueous solution, compounds 11 a ± g tend to form defined water-soluble aggregates in a self-assembling process. In methanol/water mixtures the aggregation process depends upon the configuration of the anomeric carbon in the carbohydrate moiety. The porphyrinic aggregates are characterized by strong exciton splitting in the Soret absorption spectrum and a red shift for all absorption bands. Interaction of the porphyrinic aggregates with phosphatidylethanolamine and DMPC liposomes leads to very efficient incorporation of mainly monomeric porphyrins 11 a ± g into the liposomes, as was indicated by very large binding constants. At low liposome concentrations noncovalent porphyrin dimers were detected.

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confidence: 99%

Synthesis, Self-Assembling Properties and Incorporation of Carbohydrate-Substituted Porphyrins into Cell Membrane Models

Schell

Hombrecher

1999

Chem. Eur. J.

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“…A galactopyranosyl-cholesteryl substituted porphyrin (62) was synthesized by coupling a carbohydrate substituted dipyrrylmethane (60) and cholesteryloxy substituted dipyrrylmethane (61) via an aminomethylation procedure, oxidation with K 3 [Fe(CN 6 )] and deprotection of the carbohydrate moiety with CF 3 COOH/H 2 O [54]. Due to its amphiphilic character it was possible to incorporate up to 5% of conjugate 62 into phosphatidyl ethanolamine vesicles, which are often used as a model system for cell membrane vesicles.…”

Section: Cholesterol-porphyrin Conjugatesmentioning

confidence: 99%

Steroid-photosensitizer conjugates: Syntheses and applications

Osati

Ali

Guérin

et al. 2017

J. Porphyrins Phthalocyanines

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This review focuses on progress in the development of different approaches to the design of steroid ([Formula: see text] estrogens, androgens, cholesterol) conjugates with coordination assemblies of metalloporphyrins, phthalocyanines and related complexes. Porphyrins and phthalocyanines have received considerable attention due to their novel composition, intriguing spectroscopic, photophysical, and redox properties, and potential application in light-harvesting and optoelectronic devices. With the development of more efficient imaging and therapeutic applications, these bio-conjugates are evaluated as multimodality agents (PET, fluorescence imaging) to monitor the mechanism of action of biologically active components in living systems and as agents for molecular recognition, oxygen atom transfer and catalysis. The tetrapyrrole components, which can be coupled via covalent and various non-covalent linkages, may exhibit strong interactions through efficient photo-induced electron and/or energy transfer processes.

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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%

“…A classic example is Hombrecher's work to increase the degree of amphiphilicity in the target systems through preparation of a porphyrin with both a galactopyranosyl and a cholesterin unit. 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] .…”

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 a galactopyranosyl-cholesteryloxy substituted porphyrin

Cited by 28 publications

References 12 publications

Synthesis, Self-Assembling Properties and Incorporation of Carbohydrate-Substituted Porphyrins into Cell Membrane Models

Synthesis, Self-Assembling Properties and Incorporation of Carbohydrate-Substituted Porphyrins into Cell Membrane Models

Steroid-photosensitizer conjugates: Syntheses and applications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

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