868159-50-6Relevant academic research and scientific papers
A toolbox for controlling the properties and functionalisation of hydrazone-based supramolecular hydrogels
Poolman, Jos M.,Maity, Chandan,Boekhoven, Job,Van Der Mee, Lars,Le Sage, Vincent A.A.,Groenewold, G.J. Mirjam,Van Kasteren, Sander I.,Versluis, Frank,Van Esch, Jan H.,Eelkema, Rienk
supporting information, p. 852 - 858 (2016/02/05)
In recent years, we have developed a low molecular weight hydrogelator system that is formed in situ under ambient conditions through catalysed hydrazone formation between two individually non-gelating components. In this contribution, we describe a molecular toolbox based on this system which allows us to (1) investigate the limits of gel formation and fine-tuning of their bulk properties, (2) introduce multicolour fluorescent probes in an easy fashion to enable high-resolution imaging, and (3) chemically modify the supramolecular gel fibres through click and non-covalent chemistry, to expand the functionality of the resultant materials. In this paper we show preliminary applications of this toolbox, enabling covalent and non-covalent functionalisation of the gel network with proteins and multicolour imaging of hydrogel networks with embedded mammalian cells and their substructures. Overall, the results show that the toolbox allows for on demand gel network visualisation and functionalisation, enabling a wealth of applications in the areas of chemical biology and smart materials.
Synthesis of hydrophilic conjugated porphyrin dimers for one-photon and two-photon photodynamic therapy at NIR wavelengths
Balaz, Milan,Collins, Hazel A.,Dahlstedt, Emma,Anderson, Harry L.
experimental part, p. 874 - 888 (2009/05/30)
We report the synthesis of a series of hydrophilic butadiyne-linked conjugated zinc porphyrin dimers (1-7), designed as photodynamic therapy (PDT) agents. These porphyrin dimers exhibit exceptionally high two-photon absorption cross sections (δmax≈ 8,000-17,000 GM) and red-shifted linear absorption spectra (λmax≈ 700-800 nm) making them ideal candidates for one-photon and two-photon excited photodynamic therapy. Four polar triethyleneglycol substituents are positioned along the sides of each dimer, but, on their own, these TEG chains do not confer sufficient solubility in aqueous physiological media for reproducible delivery into live cells. Charged cationic (methylpyridinium and trimethylammonium) and anionic (sulfonate and carboxylate) substituents have been appended to the meso-positions of porphyrin dimers using three synthetic strategies: 1) Suzuki coupling, 2) Sonogashira coupling, and 3) nucleophilic Senge arylation. Approaches 1 and 3 both allow attachment of aromatic substituents directly to the meso-positions of porphyrins. Approach 2 provides a route to hydrophilic porphyrin dimers with an ethyne link between the porphyrin and the polar aromatic substituent. The palladium-catalysed approaches 1 and 2 allow the synthesis of a broader range of meso-capped porphyrins, as many aryl halides are available. However the synthesis of the intermediate required for these routes necessitates a statistical reaction step, which decreases the overall yield. On the other hand, Senge-arylation provides highly regioselective nucleophilic aromatic substitution, and offers higher overall yield than the other routes. All these charged dimers exhibit good solubility in polar solvents (e.g. methanol) and aqueous solvent mixtures (aqueous DMSO or DMF).
PORPHYRIN COMPOUNDS
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Page/Page column 17-18; 24; 25; 29; 31; 33, (2008/12/04)
The present invention relates to porphyrin compounds of formula (I), to processes for preparing said compounds, to pharmaceutical compositions comprising said compounds and their use in photodynamic therapy. The porphyrin compounds exhibit high two photon absorption cross section values, are soluble and are readily absorbed by cells making them suitable for use in two photon photodynamic therapy.
Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation
McFarland, Jesse M.,Francis, Matthew B.
, p. 13490 - 13491 (2007/10/03)
An efficient transition metal catalyzed procedure for the reductive alkylation of proteins has been developed. Imines formed from the condensation of aldehydes (1 mM) with lysine residues and the N-terminus can be reduced efficiently by a [Cp*Ir(4,4′-dime
