- Synthesis and characterization of novel dendritic compounds bearing a porphyrin core and cholic acid units using "click chemistry"
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Four novel dendritic molecules bearing a porphyrin core and peripheral cholic acid units (TPPh(Zn) Tetra-CA, TPPh(2H) Tetra-CA, TPPh(Zn) Octa-CA and TPPh(2H) Octa-CA) have been synthesized by the "click chemistry" approach, using azide-alkyne couplings. These compounds are fully characterized by 1H and 13C NMR spectroscopy and MALDI-TOF. The optical properties of the dendronized porphyrins are studied by absorption and fluorescence spectroscopy in different solvents, in order to study the amphiphilic properties of the cholic acid units in combination with the optical response of the porphyrin unit. After complexation with Zn, the metallated porphyrins (TPPh(Zn) tetra-CA and TPPh(Zn) octa-CA) tend to form J-aggregates in solvents of different polarity, whereas the free base porphyrins TPPh(2H) tetra-CA and TPPh(2H) octa-CA behaved differently. The aggregation phenomenon has been investigated by varying the polarity of the environment, temperature and metallation.
- Aguilar-Ortíz, Edgar,Lévaray, Nicolas,Vonlanthen, Mireille,Morales-Espinoza, Eric G.,Rojas-Aguirre, Yareli,Zhu, Xiao Xia,Rivera, Ernesto
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- Synthesis of boronated meso-arylporphyrins via copper-catalyzed 1,3-dipolar cycloaddition reaction and their binding ability towards albumin and low density lipoproteins
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A series of novel meso- triazoloporphyrin-carborane conjugates was prepared in good yields via the copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of Zn(II) or Pd(II) 5,10,15,20-tetrakis[4-(2-propargyloxy)-2,3,5,6-tetrafluorophenyl]porphyri
- Egorov, Anton E.,Klimovich, Mikhail A.,Kononova, Elena G.,Koroleva, Olga A.,Kostyukov, Alexey A.,Kuzmin, Vladimir A.,Makarenkov, Anton V.,Markova, Alina A.,Ol'shevskaya, Valentina A.,Zaitsev, Andrei V.
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- Complexation-induced transition of nanorod to network aggregates: Alternate porphyrin and cyclodextrin arrays
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Tetrakis(permethyl-β-cyclodextrin)-modified zinc(II) porphyrin (1) and tetra(β-cyclodextrin)-modified zinc(II) porphyrin (2) were synthesized via quot;click chemistry". Intermolecular inclusion complexation of these structurally similar 1 and 2 with tetrasodium tetraphenylporphyrintetrasulfonate (3) led to formation of two distinctly different nanoarchitectures with alternate porphyrin and cyclodextrin arrays, which were proven to be network and nanorod aggregates, respectively, by using transmission electron microscopy, atomic force microscopy, and scanning electron microscopy. From the results of comparative studies in different solutions, we elucidated the mechanisms that result in nanorod to network aggregates transition, concluding that the complexation strength of porphyrin with cyclodextrin is a crucial factor to activate the potential binding sites of a molecular building block.
- Liu, Yu,Ke, Chen-Feng,Zhang, Heng-Yi,Cui, Jie,Ding, Fei
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- Topological effects and binding modes operating with multivalent iminosugar-based glycoclusters and mannosidases
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Multivalent iminosugars have been recently explored for glycosidase inhibition. Affinity enhancements due to multivalency have been reported for specific targets, which are particularly appealing when a gain in enzyme selectivity is achieved but raise the question of the binding mode operating with this new class of inhibitors. Here we describe the development of a set of tetra- and octavalent iminosugar probes with specific topologies and an assessment of their binding affinities toward a panel of glycosidases including the Jack Bean α-mannosidase (JBαMan) and the biologically relevant class II α-mannosidases from Drosophila melanogaster belonging to glycohydrolase family 38, namely Golgi α-mannosidase ManIIb (GM) and lysosomal α-mannosidase LManII (LM). Very different inhibitory profiles were observed for compounds with identical valencies, indicating that the spatial distribution of the iminosugars is critical to fine-tune the enzymatic inhibitory activity. Compared to the monovalent reference, the best multivalent compound showed a dramatic 800-fold improvement in the inhibitory potency for JBαMan, which is outstanding for just a tetravalent ligand. The compound was also shown to increase both the inhibitory activity and the selectivity for GM over LM. This suggests that multivalency could be an alternative strategy in developing therapeutic GM inhibitors not affecting the lysosomal mannosidases. Dynamic light scattering experiments and atomic force microscopy performed with coincubated solutions of the compounds with JBαMan shed light on the multivalent binding mode. The multivalent compounds were shown to promote the formation of JBαMan aggregates with different sizes and shapes. The dimeric nature of the JBαMan allows such intermolecular cross-linking mechanisms to occur.
- Brissonnet, Yoan,Ortiz Mellet, Carmen,Morandat, Sandrine,Garcia Moreno, M. Isabel,Deniaud, David,Matthews, Susan E.,Vidal, Sébastien,?esták, Sergej,El Kirat, Karim,Gouin, Sébastien G.
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- Use of 'click chemistry' for the synthesis of carbohydrate-porphyrin dendrimers and their multivalent approach toward lectin sensing
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Multivalent carbohydrate dendrimers having 12 and 36 α-d-mannose units on the periphery of a porphyrin-cored dendritic scaffold have been synthesized using 'click chemistry'. Synthesized dendrimers were characterized by 1H and 13C NM
- Das, Rituparna,Mukhopadhyay, Balaram
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- Enhanced photodynamic therapy through supramolecular photosensitizers with an adamantyl-functionalized porphyrin and a cyclodextrin dimer
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A supramolecular photosensitizer was constructed using a tetra-adamantane-functionalized porphyrin and a dimer of permethyl-β-cyclodextrin through host-guest interaction and self-assembly. The porphyrin/cyclodextrin alternating structure of supramolecular
- Xia, Lei,Wu, Jian,Huang, Baoxuan,Gao, Yun,Tian, Jia,Zhang, Weian
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- Carbon-1 versus Carbon-3 Linkage of d -Galactose to Porphyrins: Synthesis, Uptake, and Photodynamic Efficiency
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The use of glycosylated compounds is actively pursued as a therapeutic strategy for cancer due to the overexpression of various types of sugar receptors and transporters on most cancer cells. Conjugation of saccharides to photosensitizers such as porphyri
- Pereira, Patrícia M. R.,Rizvi, Waqar,Bhupathiraju, N.V.S. Dinesh K.,Berisha, Naxhije,Fernandes, Rosa,Tomé, Jo?o P.C.,Drain, Charles Michael
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- Selectivity among two lectins: Probing the effect of topology, multivalency and flexibility of "clicked" multivalent glycoclusters
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The design of multivalent glycoconjugates has been developed over the past decades to obtain high-affinity ligands for lectin receptors. While multivalency frequently increases the affinity of a ligand for its lectin through the so-called "glycoside clust
- Cecioni, Samy,Faure, Sophie,Darbost, Ulrich,Bonnamour, Isabelle,Parrot-Lopez, Helene,Roy, Olivier,Taillefumier, Claude,Wimmerova, Michaela,Praly, Jean-Pierre,Imberty, Anne,Vidal, Sebastien
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- Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate
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Although a large number of natural and non-natural metalloporphyrins are known, examples with fluorescence and fat-soluble properties are rare. We have achieved the synthesis of a fluorescent and fat-soluble zinc porphyrin incorporating four units of hydr
- Prakash Rao, H. Surya,Kamalraj,Prabakaran
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p. 4499 - 4506
(2019/02/26)
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- Synthesis, photophysical properties and anticancer activity of micro-environment sensitive amphiphilic bile acid dendrimers
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Porphyrin-cored bile acid dendrimers containing deoxymethyl cholate and methyl cholate units at the periphery, have been synthesized by convergent methodology using a click chemistry approach and characterized by 1H and 13C NMR and M
- Anandkumar, Devaraj,Raja, Rathinam,Rajakumar, Perumal
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p. 25808 - 25818
(2016/03/25)
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- Click chemistry inspired synthesis of glycoporphyrin dendrimers
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A series of porphyrin-cored glycodendrimers containing 8, 12, 16, and 24 β-d-glucopyranose units at the periphery, have been synthesized by convergent methodology using click chemistry. The structure of developed dendrimers is established by 1H
- Kushwaha, Divya,Tiwari, Vinod K.
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p. 8184 - 8190
(2013/09/12)
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