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Articles de revues sur le sujet « Foldamère »

Auteur : Grafiati

Publié le 4 juin 2021

Mis à jour le 11 janvier 2025

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1

Suhonen, Aku, Heikki Laakkonen, and Maija Nissinen. "Structural effects of hinge length variation in a versatile foldamer backbone." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C1719. http://dx.doi.org/10.1107/s2053273314082801.

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Foldamers are complex molecular scaffolds that mimic the form and function of biological molecules and are composed of simple repeating units.[1] Their potential applications include stereoselective and efficient organic catalysis mimicking the properties of enzymes, as well as bioreceptor mimics for new foldamer-protein interactions which could provide interesting possibilities for the medical industry.[2] In our previous studies we have investigated the folding properties of two oligoamides.[3] As the next step we prepared a series of aromatic oligoamide foldamers with several folding units

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2

Abramyan, Ara, Zhiwei Liu, and Vojislava Pophristic. "An ab-initio study of pyrrole and imidazole arylamides." Journal of the Serbian Chemical Society 78, no. 11 (2013): 1789–95. http://dx.doi.org/10.2298/jsc130929104a.

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Arylamide foldamers have been shown to have a number of biological and medicinal applications. For example, a class of pyrrole-imidazole polyamide foldamers is capable of binding specific DNA sequences and preventing development of various gene disorders, most importantly cancer. Molecular dynamics (MD) simulations can provide crucial details in understanding the atomic level events related to foldamer/DNA binding. An important first step in the accurate simulation of these foldamer/DNA systems is the reparametrization of force field parameters for torsion around the aryl-amide bonds. Here we

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3

Seither, Katelyn M., Heather A. McMahon, Nikita Singh та ін. "Specific aromatic foldamers potently inhibit spontaneous and seeded Aβ42 and Aβ43 fibril assembly". Biochemical Journal 464, № 1 (2014): 85–98. http://dx.doi.org/10.1042/bj20131609.

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We report specific aromatic foldamers that inhibit fibrillization by amyloid-β (Aβ) peptides connected with Alzheimer's disease. One foldamer inhibits formation of toxic Aβ-species as well as the self-templating activity of Aβ fibrils, properties that could have therapeutic utility.

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4

Tsuchiya, Keisuke, Takashi Kurohara, Kiyoshi Fukuhara, Takashi Misawa, and Yosuke Demizu. "Helical Foldamers and Stapled Peptides as New Modalities in Drug Discovery: Modulators of Protein-Protein Interactions." Processes 10, no. 5 (2022): 924. http://dx.doi.org/10.3390/pr10050924.

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A “foldamer” is an artificial oligomeric molecule with a regular secondary or tertiary structure consisting of various building blocks. A “stapled peptide” is a peptide with stabilized secondary structures, in particular, helical structures by intramolecular covalent side-chain cross-linking. Helical foldamers and stapled peptides are potential drug candidates that can target protein-protein interactions because they enable multipoint molecular recognition, which is difficult to achieve with low-molecular-weight compounds. This mini-review describes a variety of peptide-based foldamers and sta

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5

Choi, Sungwook, Andre Isaacs, Dylan Clements, et al. "De novo design and in vivo activity of conformationally restrained antimicrobial arylamide foldamers." Proceedings of the National Academy of Sciences 106, no. 17 (2009): 6968–73. http://dx.doi.org/10.1073/pnas.0811818106.

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The emergence of drug-resistant bacteria has compromised the use of many conventional antibiotics, leading to heightened interest in a variety of antimicrobial peptides. Although these peptides have attractive potential as antibiotics, their size, stability, tissue distribution, and toxicity have hampered attempts to harness these capabilities. To address such issues, we have developed small (molecular mass <1,000 Da) arylamide foldamers that mimic antimicrobial peptides. Hydrogen-bonded restraints in the arylamide template rigidify the conformation via hydrogen bond formation and increase

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6

Bartus, Éva, Gábor Olajos, Ildikó Schuster, et al. "Structural Optimization of Foldamer-Dendrimer Conjugates as Multivalent Agents against the Toxic Effects of Amyloid Beta Oligomers." Molecules 23, no. 10 (2018): 2523. http://dx.doi.org/10.3390/molecules23102523.

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Alzheimer’s disease is one of the most common chronic neurodegenerative disorders. Despite several in vivo and clinical studies, the cause of the disease is poorly understood. Currently, amyloid β (Aβ) peptide and its tendency to assemble into soluble oligomers are known as a main pathogenic event leading to the interruption of synapses and brain degeneration. Targeting neurotoxic Aβ oligomers can help recognize the disease at an early stage or it can be a potential therapeutic approach. Unnatural β-peptidic foldamers are successfully used against many different protein targets due to their fa

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7

Tallet, Lorène, Emilie Frisch, Mégane Bornerie, et al. "Design of Oligourea-Based Foldamers with Antibacterial and Antifungal Activities." Molecules 27, no. 5 (2022): 1749. http://dx.doi.org/10.3390/molecules27051749.

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There is an urgent need to develop new therapeutic strategies to fight the emergence of multidrug resistant bacteria. Many antimicrobial peptides (AMPs) have been identified and characterized, but clinical translation has been limited partly due to their structural instability and degradability in physiological environments. The use of unnatural backbones leading to foldamers can generate peptidomimetics with improved properties and conformational stability. We recently reported the successful design of urea-based eukaryotic cell-penetrating foldamers (CPFs). Since cell-penetrating peptides an

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8

Legrand, Baptiste, Julie Aguesseau-Kondrotas, Matthieu Simon, and Ludovic Maillard. "Catalytic Foldamers: When the Structure Guides the Function." Catalysts 10, no. 6 (2020): 700. http://dx.doi.org/10.3390/catal10060700.

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Enzymes are predominantly proteins able to effectively and selectively catalyze highly complex biochemical reactions in mild reaction conditions. Nevertheless, they are limited to the arsenal of reactions that have emerged during natural evolution in compliance with their intrinsic nature, three-dimensional structures and dynamics. They optimally work in physiological conditions for a limited range of reactions, and thus exhibit a low tolerance for solvent and temperature conditions. The de novo design of synthetic highly stable enzymes able to catalyze a broad range of chemical reactions in v

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9

Nowak-Król, Agnieszka, Benjamin Fimmel, Minjung Son, Dongho Kim, and Frank Würthner. "Photoinduced electron transfer (PET) versus excimer formation in supramolecular p/n-heterojunctions of perylene bisimide dyes and implications for organic photovoltaics." Faraday Discussions 185 (2015): 507–27. http://dx.doi.org/10.1039/c5fd00052a.

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Foldamer systems comprised of two perylene bisimide (PBI) dyes attached to the conjugated backbones of 1,2-bis(phenylethynyl)benzene and phenylethynyl-bis(phenylene)indane, respectively, were synthesized and investigated with regard to their solvent-dependent properties. UV/Vis absorption and steady-state fluorescence spectra show that both foldamers exist predominantly in a folded H-aggregated state consisting of π–π-stacked PBIs in THF and in more random conformations with weaker excitonic coupling between the PBIs in chloroform. Time-resolved fluorescence spectroscopy and transient absorpti

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10

Giuffrida, Simone Giuseppe, Weronika Forysiak, Pawel Cwynar, and Roza Szweda. "Shaping Macromolecules for Sensing Applications—From Polymer Hydrogels to Foldamers." Polymers 14, no. 3 (2022): 580. http://dx.doi.org/10.3390/polym14030580.

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Sensors are tools for detecting, recognizing, and recording signals from the surrounding environment. They provide measurable information on chemical or physical changes, and thus are widely used in diagnosis, environment monitoring, food quality checks, or process control. Polymers are versatile materials that find a broad range of applications in sensory devices for the biomedical sector and beyond. Sensory materials are expected to exhibit a measurable change of properties in the presence of an analyte or a stimulus, characterized by high sensitivity and selectivity of the signal. Signal pa

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11

Tomasini, Claudia, Ivan Huc, David J. Aitken, and Ferenc Fülöp. "Foldamers." European Journal of Organic Chemistry 2013, no. 17 (2013): 3408–9. http://dx.doi.org/10.1002/ejoc.201300676.

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12

Alex, Jimi M., Valentina Corvaglia, Xiaobo Hu, Sylvain Engilberge, Ivan Huc, and Peter B. Crowley. "Crystal structure of a protein–aromatic foldamer composite: macromolecular chiral resolution." Chemical Communications 55, no. 74 (2019): 11087–90. http://dx.doi.org/10.1039/c9cc05330a.

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13

Rinaldi, Samuele. "The Diverse World of Foldamers: Endless Possibilities of Self-Assembly." Molecules 25, no. 14 (2020): 3276. http://dx.doi.org/10.3390/molecules25143276.

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Different classes of foldamers, which are synthetic oligomers that adopt well-defined conformations in solution, have been the subject of extensive studies devoted to the elucidation of the forces driving their secondary structures and their potential as bioactive molecules. Regardless of the backbone type (peptidic or abiotic), the most important features of foldamers are the high stability, easy predictability and tunability of their folding, as well as the possibility to endow them with enhanced biological functions, with respect to their natural counterparts, by the correct choice of monom

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14

Xu, Lina, Guoyong Fang, and Shuhua Li. "Supramolecular catalysis in the methylation of meta-phenylene ethynylene foldamer containing N,N-dimethylaminopyridine." RSC Advances 7, no. 23 (2017): 14046–52. http://dx.doi.org/10.1039/c7ra00710h.

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DFT investigations show that the methylation reaction of N,N-dimethylaminopyridine (DMAP)-modified meta-phenylene ethynylene foldamer can be catalyzed by the noncovalent interactions between the foldamer and the methyl sulfonate esters.

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15

Guichard, Gilles, and Ivan Huc. "Synthetic foldamers." Chemical Communications 47, no. 21 (2011): 5933. http://dx.doi.org/10.1039/c1cc11137j.

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16

Prabhakaran, Panchami, Gowri Priya, and Gangadhar J. Sanjayan. "Foldamere: Anwendungen jenseits der Biomedizin." Angewandte Chemie 124, no. 17 (2012): 4079–81. http://dx.doi.org/10.1002/ange.201107521.

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17

Kudo, Mayumi, Victor Maurizot, Hyuma Masu, Aya Tanatani, and Ivan Huc. "Structural elucidation of foldamers with no long range conformational order." Chem. Commun. 50, no. 70 (2014): 10090–93. http://dx.doi.org/10.1039/c4cc03822c.

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18

Saito, Ami. "Foldamer Catalysts." Journal of Synthetic Organic Chemistry, Japan 79, no. 9 (2021): 871–72. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.871.

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19

Girvin, Zebediah C., and Samuel H. Gellman. "Foldamer Catalysis." Journal of the American Chemical Society 142, no. 41 (2020): 17211–23. http://dx.doi.org/10.1021/jacs.0c07347.

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20

Faour, Lara, Catherine Adam, Christelle Gautier, et al. "Redox-controlled hybridization of helical foldamers." Chemical Communications 55, no. 40 (2019): 5743–46. http://dx.doi.org/10.1039/c9cc02498k.

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21

Gellman, Samuel H. "Foldamers: A Manifesto." Accounts of Chemical Research 31, no. 4 (1998): 173–80. http://dx.doi.org/10.1021/ar960298r.

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22

Juwarker, Hemraj, and Kyu-Sung Jeong. "Anion-controlled foldamers." Chemical Society Reviews 39, no. 10 (2010): 3664. http://dx.doi.org/10.1039/b926162c.

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23

Huc, Ivan. "Aromatic Oligoamide Foldamers." European Journal of Organic Chemistry 2004, no. 1 (2004): 17–29. http://dx.doi.org/10.1002/ejoc.200300495.

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24

Adam, Catherine, Lara Faour, Valérie Bonnin, et al. "Supramolecular chemistry of helical foldamers at the solid–liquid interface: self-assembled monolayers and anion recognition." Chemical Communications 55, no. 58 (2019): 8426–29. http://dx.doi.org/10.1039/c9cc03851e.

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25

Farkas, Viktor, Adrienn Nagy, Dóra K. Menyhárd, and András Perczel. "Assignment of Vibrational Circular Dichroism Cross‐Referenced Electronic Circular Dichroism Spectra of Flexible Foldamer Building Blocks: Towards Assigning Pure Chiroptical Properties of Foldamers." Chemistry – A European Journal 25, no. 65 (2019): 14890–900. http://dx.doi.org/10.1002/chem.201903023.

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26

Kirinda, Viraj C., and C. Scott Hartley. "Folding-controlled assembly of ortho-phenylene-based macrocycles." Chemical Science 12, no. 20 (2021): 6992–7002. http://dx.doi.org/10.1039/d1sc01270c.

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27

Martín-Lasanta, Ana, Luis Álvarez de Cienfuegos, Alice Johnson, et al. "Novel ortho-OPE metallofoldamers: binding-induced folding promoted by nucleating Ag(i)–alkyne interactions." Chem. Sci. 5, no. 12 (2014): 4582–91. http://dx.doi.org/10.1039/c4sc01988a.

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28

Zheng, Dan, Shengzhu Guo, Lu Zheng, Qi Xu, Ying Wang, and Hua Jiang. "Red circularly polarized luminescence from intramolecular excimers restricted by chiral aromatic foldamers." Chemical Communications 57, no. 90 (2021): 12016–19. http://dx.doi.org/10.1039/d1cc05163f.

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29

Kim, Jee Seon, Hae-Geun Jeon, and Kyu-Sung Jeong. "Modulation of helix stability of indolocarbazole–pyridine hybrid foldamers." Chemical Communications 52, no. 16 (2016): 3406–9. http://dx.doi.org/10.1039/c6cc00045b.

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30

Liu, Rui, Shuang Cheng, Erin S. Baker, Richard D. Smith, Xiao Cheng Zeng, and Bing Gong. "Surprising impact of remote groups on the folding–unfolding and dimer-chain equilibria of bifunctional H-bonding unimers." Chemical Communications 52, no. 19 (2016): 3773–76. http://dx.doi.org/10.1039/c6cc00224b.

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31

Pérez de Carvasal, Kévan, Nesrine Aissaoui, Gérard Vergoten, et al. "Folding of phosphodiester-linked donor–acceptor oligomers into supramolecular nanotubes in water." Chemical Communications 57, no. 34 (2021): 4130–33. http://dx.doi.org/10.1039/d1cc01064f.

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32

Méndez-Ardoy, Alejandro, Nagula Markandeya, Xuesong Li, et al. "Multi-dimensional charge transport in supramolecular helical foldamer assemblies." Chemical Science 8, no. 10 (2017): 7251–57. http://dx.doi.org/10.1039/c7sc03341a.

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33

Shang, Jie, Wei Zhao, Xichen Li, Ying Wang, and Hua Jiang. "Aryl-triazole foldamers incorporating a pyridinium motif for halide anion binding in aqueous media." Chemical Communications 52, no. 24 (2016): 4505–8. http://dx.doi.org/10.1039/c5cc10422j.

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34

Tsiamantas, Christos, Sunbum Kwon, Céline Douat, Ivan Huc, and Hiroaki Suga. "Optimizing aromatic oligoamide foldamer side-chains for ribosomal translation initiation." Chemical Communications 55, no. 51 (2019): 7366–69. http://dx.doi.org/10.1039/c9cc03547h.

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35

Cai, Jiajia, and Jonathan L. Sessler. "Neutral CH and cationic CH donor groups as anion receptors." Chem. Soc. Rev. 43, no. 17 (2014): 6198–213. http://dx.doi.org/10.1039/c4cs00115j.

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36

Le Bailly, Bryden A. F., and Jonathan Clayden. "Dynamic foldamer chemistry." Chemical Communications 52, no. 27 (2016): 4852–63. http://dx.doi.org/10.1039/c6cc00788k.

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37

Ikkanda, B. A., and B. L. Iverson. "Exploiting the interactions of aromatic units for folding and assembly in aqueous environments." Chemical Communications 52, no. 50 (2016): 7752–59. http://dx.doi.org/10.1039/c6cc01861k.

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38

Ingole, Tukaram S., Sangram S. Kale, Sukumaran Santhosh Babu, and Gangadhar J. Sanjayan. "Self-assembled vesicles of urea-tethered foldamers as hydrophobic drug carriers." Chemical Communications 52, no. 71 (2016): 10771–74. http://dx.doi.org/10.1039/c6cc05079d.

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39

Kann, Nina, Johan R. Johansson, and Tamás Beke-Somfai. "Conformational properties of 1,4- and 1,5-substituted 1,2,3-triazole amino acids – building units for peptidic foldamers." Organic & Biomolecular Chemistry 13, no. 9 (2015): 2776–85. http://dx.doi.org/10.1039/c4ob02359e.

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40

Kale, Sangram S., Shrikant M. Kunjir, Rupesh L. Gawade, Vedavati G. Puranik, P. R. Rajamohanan та Gangadhar J. Sanjayan. "Conformational modulation of peptide secondary structures using β-aminobenzenesulfonic acid". Chem. Commun. 50, № 22 (2014): 2886–88. http://dx.doi.org/10.1039/c3cc48850k.

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41

Chandramouli, Nagula, Mohammed Farrag El-Behairy, Guillaume Lautrette, Yann Ferrand, and Ivan Huc. "Polar solvent effects on tartaric acid binding by aromatic oligoamide foldamer capsules." Organic & Biomolecular Chemistry 14, no. 8 (2016): 2466–72. http://dx.doi.org/10.1039/c5ob02641e.

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42

Helttunen, Kaisa, Riia Annala, Aku Suhonen, Elisa Nauha, Juha Linnanto, and Maija Nissinen. "Supramolecular chirality and symmetry breaking of fluoride complexes of achiral foldamers." CrystEngComm 19, no. 35 (2017): 5184–87. http://dx.doi.org/10.1039/c7ce01109a.

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43

Lee, Chaeeun, Hyemi Lee, Seungwon Lee, Hae-Geun Jeon, and Kyu-Sung Jeong. "Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers." Organic Chemistry Frontiers 6, no. 3 (2019): 299–303. http://dx.doi.org/10.1039/c8qo01307a.

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44

Collie, G. W., K. Pulka-Ziach, and G. Guichard. "Surfactant-facilitated crystallisation of water-soluble foldamers." Chemical Science 7, no. 5 (2016): 3377–83. http://dx.doi.org/10.1039/c6sc00090h.

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45

Koppireddi, Satish, Chuan-Zhi Liu, Hui Wang, Dan-Wei Zhang, and Zhan-Ting Li. "Halogen and hydrogen bonding-driven self-assembly of supramolecular macrocycles and double helices from hydrogen-bonded arylamide foldamers." CrystEngComm 21, no. 16 (2019): 2626–30. http://dx.doi.org/10.1039/c8ce02187b.

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46

Toya, Michihisa, Hideto Ito, and Kenichiro Itami. "Synthesis and properties of helically-folded poly(arylenediethynylene)s." Polymer Chemistry 12, no. 22 (2021): 3290–98. http://dx.doi.org/10.1039/d1py00144b.

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47

Kudo, Mayumi, and Aya Tanatani. "Conformational properties of aromatic multi-layered and helical oligoureas and oligoguanidines." New Journal of Chemistry 39, no. 5 (2015): 3190–96. http://dx.doi.org/10.1039/c4nj01885k.

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48

Diemer, Vincent, Julien Maury, Bryden A. F. Le Bailly, Simon J. Webb, and Jonathan Clayden. "Dibenzazepinyl ureas as dual NMR and CD probes of helical screw-sense preference in conformationally equilibrating dynamic foldamers." Chemical Communications 53, no. 78 (2017): 10768–71. http://dx.doi.org/10.1039/c7cc06427f.

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49

Liu, Ya-Zhou, Xiao Mu, Cheih-Kai Chan, Koen Robeyns, Cheng-Chung Wang, and Michael L. Singleton. "Water binding stabilizes stacked conformations of ferrocene containing sheet-like aromatic oligoamides." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5521–24. http://dx.doi.org/10.1039/d1ob00580d.

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50

Yuan, Dafei, Mohammad A. Awais, Valerii Sharapov, et al. "Foldable semi-ladder polymers: novel aggregation behavior and high-performance solution-processed organic light-emitting transistors." Chemical Science 11, no. 41 (2020): 11315–21. http://dx.doi.org/10.1039/d0sc04068a.

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