181425-91-2Relevant articles and documents
Fluorescence quenching and size selective heterodimerization of a porphyrin adsorbed to gold and embedded in rigid membrane gaps
Fudickar, Werner,Zimmermann, J?rg,Ruhlmann, Laurent,Schneider, Johannes,R?der, Beate,Siggel, Ulrich,Fuhrhop, Jürgen-Hinrich
, p. 9539 - 9545 (1999)
Octaanionic meso-tetra(3,5-dicarboxylatophenyl) porphyrin 1 was adsorbed to gold electrodes at pH 12 and stayed there after repeated washing with 10- 2 M KOH. The fluorescence on sputtered gold surfaces amounted to 10% of the intensi
Anionic hexadeca-carboxylate tetrapyrazinoporphyrazine: Synthesis and in vitro photodynamic studies of a water-soluble, non-aggregating photosensitizer
MacHacek, Miloslav,Kollár, Jan,Miletin, Miroslav,Ku?era, Radim,Kubát, Pavel,Simunek, Tomas,Novakova, Veronika,Zimcik, Petr
, p. 10064 - 10077 (2016/02/05)
A sodium salt of zinc tetrapyrazinoporphyrazine bearing eight 3,5-dicarboxylatophenyl substituents (1) was synthesized. The presence of sixteen negative charges in a rigid arrangement on the periphery of the macrocycle inhibited its aggregation in water or buffers at pH > 5.8. Strong aggregation was, however, observed in buffers at pH 50 = 5.7 ± 1.1 μM) was found to be influenced by both pH and interactions with serum proteins. This was demonstrated with a detailed in vitro study based on the inhibition of vacuolar H+-ATPase using bafilomycin A1, which increased the intracellular fluorescence of 1. Compound 1 also formed interactions with serum proteins that partially quenched its excited states; however, they also protected the compound from self-aggregation at low pH.
Viologen-based benzylic dendrimers: selective synthesis of 3,5-bis(hydroxymethyl)benzylbromide and conformational analysis of the corresponding viologen dendrimer subunit
Kathiresan, Murugavel,Walder, Lorenz,Ye, Fei,Reuter, Hans
supporting information; experimental part, p. 2188 - 2192 (2010/06/19)
Convergent and divergent strategies for the synthesis of viologen dendrimers with 1,3,5-tri-methylene-branching units are discussed. The title compound is easily transformed into 1-[3,5-bis(hydroxymethyl)benzyl]-4-(pyridin-4-yl)pyridinium hexafluorophosphate, which is used in sequential growth and activation steps as a CB2 compound in the cascade-type dendrimer synthesis (B = -OH, activation = -OH → Br). Analysis of the dendrimer structure reveals that three torsional angles, that is, τ1 between the two pyridinium units, τ2 between the methylene and pyridinium and τ3 between the methylene and phenyl, determine the conformational space of the dendrimers. We report here the crystal structure of 1-[3,5-bis(hydroxymethyl)benzyl]-4-(pyridin-4-yl)pyridinium as PF6- salt which represents the smallest subunit of the dendrimer that shows the same three torsional angles. The crystal structure together with the results from PM3 calculations opens an avenue to judge the structure of benzylic viologen-based dendrimers.
Synthesis and supramolecular properties of a novel octaphosphonate porphyrin
Bhosale, Sheshanath V.,Kalyankar, Mohan B.,Langibrd, Steven J.,Bhosale, Sidhanath V.,Oliver, Ruth F.
experimental part, p. 4128 - 4134 (2009/12/26)
Two complementary routes were developed for preparing novel octaphosphonate porphyrins. The use of protected/deprotected phosphonate-substituted precursors in the rational synthesis gave an overall yield 16%. A more streamlined synthetic path gave 21 % overall yield, of the target molecule. Octaphosphonate porphyrin possesses promising properties in supramolecular aggregate formation with cyclam. Cofacial reversible self-assembly of a meso-substituted octaphosphonate porphyrin with cyclam yields micrometer-long nanowires with a height of about 1-1.5 nm. The resulting wires were characterized by UV/Vis absorption, emission and atomic force microscopy and transmission electron microscopy. ( Wiley-VCH Verlag GmbH & Co. KGaA.
Potent and selective isophthalamide S2 hydroxyethylamine inhibitors of BACE1
Kortum, Steven W.,Benson, Timothy E.,Bienkowski, Michael J.,Emmons, Thomas L.,Prince, D. Bryan,Paddock, Donna J.,Tomasselli, Alfredo G.,Moon, Joseph B.,LaBorde, Alice,TenBrink, Ruth E.
, p. 3378 - 3383 (2008/02/09)
The design and synthesis of a novel series of potent BACE1 hydroxyethylamine inhibitors. These inhibitors feature hydrogen bonding substituents at the C-5 position of the isophthalamide ring with improved selectivity over cathepsin D.
Efficient charge injection from the S2 photoexcited state of special-pair mimic porphyrin assemblies anchored on a titanium-modified ITO anode
Morisue, Mitsuhiko,Haruta, Noriko,Kalita, Dipak,Kobuke, Yoshiaki
, p. 8123 - 8135 (2007/10/03)
A novel surface fabrication methodology has been accomplished, aimed at efficient anodic photocurrent generation by a photoexcited porphyrin on an ITO (indium-tin oxide) electrode. The ITO electrode was submitted to a surface sol-gel process with titanium
Synthesis, structural, EPR and magnetic analysis of nitronyl-nitroxide labelled isophthalic acid
Felix, Olivier,Hosseini, Mir Wais,De Cian, Andre,Fischer, Jean,Catala, Laure,Turek, Philippe
, p. 2943 - 2946 (2007/10/03)
The high yield synthesis of an isophthalic acid derivative bearing a nitronyl-nitroxide moiety at the 5-position was achieved. The structural analysis in the crystalline phase by X-ray diffraction on single crystals revealed the formation of a 3-D network through strong H-bonds between the acid groups and the nitronyl-nitroxide moieties. The spin label obtained was also analysed by EPR spectroscopy which showed a five line pattern with a(N)=7.51 G and a g-factor of 2.0066. Magnetic measurements revealed that at low temperature, the systeme showed a Curie-Weiss like behaviour with weak ferromagnetic intermolecular interactions.
Isophthalate ester-terminated dendrimers: Versatile nanoscopic building blocks with readily modifiable surface functionalities
Leon, Jeffrey W.,Kawa, Manabu,Fréchet, Jean M. J.
, p. 8847 - 8859 (2007/10/03)
The preparation and modification of highly functionalized polyether dendrimers containing a versatile diethyl isophthalate terminal group is presented. The convergent synthesis consists of the construction of diester-terminated dendrons containing benzylic bromide functions at the focal point and their subsequent attachment to 4,4'-biphenol cores. Dendrons up to the third generation can be prepared using recrystallization alone as the primary means of purification, allowing the synthesis to be performed on the scale of tens to hundreds of grams. The third and fourth generation bidendron dendrimers (with 32 and 64 terminal ester functionalities, respectively) have been subjected to a variety of surface modification reactions including hydrolysis, ester interchange, and amide-ester interchange, many of which proceed with complete conversion of the functional groups and in high isolated yield. The addition of alcohols such as benzyl alcohol or a first generation 3,5-di(benzyloxy)benzyl alcohol dendron to the dendrimer surface serves to increase the generation number of the dendrimers by one or two in what amounts to a 'double convergent growth' approach. The analysis of these structurally precise dendrimers by matrix-assisted laser desorption ionization time of flight is described.
