Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH

Scholarly Works

• Rivero-Barbarroja, G.; Fernández-Clavero, C.; García-Iriepa, C.; Marcelo, G.; Padilla-Pérez, M. C.; Neva, T.; Benito, J. M.; Maisonneuve, S.; Ortiz Mellet, C.; Xie, J.; García Fernández, J. M.; Mendicuti, F. Reversible Light-Induced Dimerization of Secondary Face Azobenzene-Functionalized β-Cyclodextrin Derivatives. The Journal of organic chemistry 2023, 88, 8674–8689. doi:10.1021/acs.joc.3c00564
• Wang, Z.; Maisonneuve, S.; Xie, J. One-Pot Synthesis of Water-Soluble Glycosyl Azobenzenes and Their Photoswitching Properties in Water. The Journal of organic chemistry 2022, 87, 16165–16174. doi:10.1021/acs.joc.2c01511
• Volarić, J.; Buter, J.; Schulte, A. M.; van den Berg, K.-O.; Santamaría-Aranda, E.; Szymanski, W.; Feringa, B. L. Design and Synthesis of Visible-Light-Responsive Azobenzene Building Blocks for Chemical Biology. The Journal of organic chemistry 2022, 87, 14319–14333. doi:10.1021/acs.joc.2c01777
• Das, K.; Singh, V.; Gardas, R. L. Cationic Amphiphilic Molecules as Bactericidal Agents. Alternatives to Antibiotics; Springer Nature Singapore, 2022; pp 277–302. doi:10.1007/978-981-19-1854-4_11
• Despras, G.; Poonthiyil, V.; Lindhorst, T. K. doi:10.1002/9783527827626.ch41
• Osswald, U.; Boneberg, J.; Wittmann, V. Photoswitching Affinity and Mechanism of Multivalent Lectin Ligands. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202200267. doi:10.1002/chem.202200267
• Volarić, J.; Szymanski, W.; Simeth, N. A.; Feringa, B. L. Molecular photoswitches in aqueous environments. Chemical Society reviews 2021, 50, 12377–12449. doi:10.1039/d0cs00547a
• Cheng, H. B.; Zhang, S.; Qi, J.; Liang, X.-J.; Yoon, J. Advances in Application of Azobenzene as a Trigger in Biomedicine: Molecular Design and Spontaneous Assembly. Advanced materials (Deerfield Beach, Fla.) 2021, 33, 2007290. doi:10.1002/adma.202007290
• Léonard, E.; Fayeulle, A. Azo-Dyes-Grafted Oligosaccharides-From Synthesis to Applications. Molecules (Basel, Switzerland) 2021, 26, 3063. doi:10.3390/molecules26113063
• Damalanka, V. C.; Maddirala, A. R.; Janetka, J. W. Novel approaches to glycomimetic design: development of small molecular weight lectin antagonists. Expert opinion on drug discovery 2021, 16, 513–536. doi:10.1080/17460441.2021.1857721
• Despras, G.; Möckl, L.; Heitmann, A.; Stamer, I.; Bräuchle, C.; Lindhorst, T. K. A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand Orientation in Bacterial Adhesion. Chembiochem : a European journal of chemical biology 2019, 20, 2373–2382. doi:10.1002/cbic.201900269
• Kolbe, K.; Veleti, S. K.; Reiling, N.; Lindhorst, T. K. Lectins of Mycobacterium tuberculosis - rarely studied proteins. Beilstein journal of organic chemistry 2019, 15, 1–15. doi:10.3762/bjoc.15.1
• Hüll, K.; Morstein, J.; Trauner, D. In Vivo Photopharmacology. Chemical reviews 2018, 118, 10710–10747. doi:10.1021/acs.chemrev.8b00037
• Harvey, D. Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2013–2014. Mass spectrometry reviews 2018, 37, 353–491. doi:10.1002/mas.21530
• Salta, J.; Benhamou, R. I.; Herzog, I. M.; Fridman, M. Tuning the Effects of Bacterial Membrane Permeability through Photo‐Isomerization of Antimicrobial Cationic Amphiphiles. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 12724–12728. doi:10.1002/chem.201703010
• Mydock-McGrane, L.; Hannan, T. J.; Janetka, J. W. Rational design strategies for FimH antagonists: new drugs on the horizon for urinary tract infection and Crohn’s disease. Expert opinion on drug discovery 2017, 12, 711–731. doi:10.1080/17460441.2017.1331216
• Müller, C.; Despras, G.; Lindhorst, T. K. Organizing multivalency in carbohydrate recognition. Chemical Society reviews 2016, 45, 3275–3302. doi:10.1039/c6cs00165c
• Müller, A.; Kobarg, H.; Chandrasekaran, V.; Gronow, J.; Sönnichsen, F. D.; Lindhorst, T. K. Synthesis of Bifunctional Azobenzene Glycoconjugates for Cysteine‐Based Photosensitive Cross‐Linking with Bioactive Peptides. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 13723–13731. doi:10.1002/chem.201501571
• Hain, J.; Chandrasekaran, V.; Lindhorst, T. K. Joining Hydroxyazobenzene and Mannose under Mitsunobu Conditions. Israel Journal of Chemistry 2015, 55, 383–386. doi:10.1002/ijch.201400211
• Hu, Y.; Tabor, R. F.; Wilkinson, B. L. Sweetness and light: design and applications of photo-responsive glycoconjugates. Organic & biomolecular chemistry 2015, 13, 2216–2225. doi:10.1039/c4ob02296c

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