16169-22-5Relevant articles and documents
β-Cyclodextrin-glycerol dimers: Synthesis and NMR conformational analysis
Legros, Vanessa,Vanhaverbeke, Cecile,Souard, Florence,Len, Christophe,Desire, Jerome
, p. 2583 - 2590 (2013)
The synthesis of new β-cyclodextrin dimers linked through their primary faces by different glycerol-like moieties by click chemistry is described. The unusual behaviour of these cyclodextrin-glycerol dimers in aqueous solution has been studied by NMR spec
Pillar[5]arene-Based Polycationic Glyco[2]rotaxanes Designed as Pseudomonas aeruginosa Antibiofilm Agents
Coenye, Tom,De Winter, Julien,Diaconu, Andrei,Fransolet, Maude,Gillon, Emilie,Imberty, Anne,Jimmidi, Ravikumar,Michiels, Carine,Mohy El Dine, Tharwat,Vincent, Stéphane P.
supporting information, p. 14728 - 14744 (2021/10/12)
Pseudomonas aeruginosa (P.A.) is a human pathogen belonging to the top priorities for the discovery of new therapeutic solutions. Its propensity to generate biofilms strongly complicates the treatments required to cure P.A. infections. Herein, we describe the synthesis of a series of novel rotaxanes composed of a central galactosylated pillar[5]arene, a tetrafucosylated dendron, and a tetraguanidinium subunit. Besides the high affinity of the final glycorotaxanes for the two P.A. lectins LecA and LecB, potent inhibition levels of biofilm growth were evidenced, showing that their three subunits work synergistically. An antibiofilm assay using a double δlecAδlecB mutant compared to the wild type demonstrated that the antibiofilm activity of the best glycorotaxane is lectin-mediated. Such antibiofilm potency had rarely been reached in the literature. Importantly, none of the final rotaxanes was bactericidal, showing that their antibiofilm activity does not depend on bacteria killing, which is a rare feature for antibiofilm agents.
Synthesis and anticancer activity of dimeric podophyllotoxin derivatives
Zi, Cheng-Ting,Yang, Liu,Xu, Feng-Qing,Dong, Fa-Wu,Yang, Dan,Li, Yan,Zhou, Jun,Hu, Jiang-Miao,Ding, Zhong-Tao,Jiang, Zi-Hua
, p. 3393 - 3406 (2019/04/26)
Background: Podophyllotoxin is a potent cytotoxic agent and serves as a useful lead compound for the development of antitumor drugs. Several podophyllotoxin-derived antitumor agents, including etoposide, are currently in clinical use; however, their therapeutic efficacy is often limited due to side effects and the development of resistance by cancer cells. Previous studies have shown that 4Β-1,2,3-triazole derivatives of podophyllotoxin exhibit more potent anticancer activity and better binding to topoisomerase-II than etoposide. The effect of dimerization of such derivatives on the anticancer activity has not been studied. Methods: Two moieties of podophyllotoxin were linked at the C-4 position via 1,2,3-triazole rings to give a series of novel dimeric podophyllotoxin derivatives. 4Β-Azido-substituted podophyllotoxin derivatives (23 and 24) were coupled with various dipropargyl functionalized linkers by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction to provide dimeric products in very good yield. The in vitro anticancer activity of the synthesized compounds was evaluated by MTT assay against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480). The normal BEAS-2B (lung) cell line was also included for study in order to evaluate the cancer selectivity of the most active compound as compared with normal cells. Results: A group of 16 dimeric podophyllotoxin derivatives with different linkers were synthesized and structurally characterized. Most compounds do not show significant cytotoxicity (IC50 > 40 mM) against all five cancer cell lines. However, one compound (29) which bears a perbutyrylated glucose residue on the glycerol linker is highly potent against all five cancer cell lines tested, with IC50 values ranging from 0.43 to 3.50 μM. This compound (29) also shows good selectivity towards cancer cell lines as compared with the normal BEAS-2B (lung) cell line, showing selectivity indexes from 4.4 to 35.7. Conclusion: The anticancer activity of dimeric podophyllotoxin derivatives is generally speaking not improved as compared to their monomeric counterparts, and the potency of these dimeric derivatives can be largely affected by the nature of the linker between the two moieties. Among the synthesized derivatives, compound 29 is significantly more cytotoxic and selective towards cancer cells than etoposide and cisplatin, which are currently in clinical use. Compound 29 is a promising anticancer drug and needs further studies.
Spatially well-defined carbohydrate nanoplatforms: Synthesis, characterization and lectin interaction study
Timmer,Flos, M. Abellán,J?rgensen, L. M?nster,Proverbio,Altun,Ramstr?m,Aastrup,Vincent
supporting information, p. 12326 - 12329 (2016/10/22)
Two novel dodecasubstituted carbohydrate nanoplatforms based on molecular Borromean rings and dodecaamine cages have been prepared for use in evaluating the importance of the spatial distribution of carbohydrates in their interaction with lectins. The binding affinities of the glyconanoplatforms were characterized using quartz crystal microbalance technology and compared with a monovalent reference and dodecaglycosylated fullerenes.
