Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

Article

Galante, E., Geraci, Corrada, Sciuto, Sebastiano, Campo, Vanessa L., Carvalho, Ivone, Sesti-Costa, Renata, Guedes, Paulo M.M., Silva, João S., Hill, Lionel, Nepogodiev, Sergey A. and Field, Robert A. 2011. Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity. Tetrahedron. 67 (33), pp. 5902-5912. https://doi.org/10.1016/j.tet.2011.06.065
AuthorsGalante, E., Geraci, Corrada, Sciuto, Sebastiano, Campo, Vanessa L., Carvalho, Ivone, Sesti-Costa, Renata, Guedes, Paulo M.M., Silva, João S., Hill, Lionel, Nepogodiev, Sergey A. and Field, Robert A.
Abstract

A new series of water-soluble tetravalent glycoclusters incorporating β-lactosyl residues attached to a central calix[4]arene core was synthesised using azide–alkyne Cu(I)-catalysed cycloaddition (‘click chemistry’). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14–21 atom spacer arms. The glycoclusters with a C4-symmetrical arrangement of β-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays.

JournalTetrahedron
Journal citation67 (33), pp. 5902-5912
ISSN00404020
Year2011
PublisherElsevier
Digital Object Identifier (DOI)https://doi.org/10.1016/j.tet.2011.06.065
Web address (URL)https://doi.org/10.1016/j.tet.2011.06.065
Publication dates
Print19 Aug 2011
Publication process dates
Deposited18 Aug 2017
Accepted20 Jun 2011
Copyright information© Elsevier 2011
Permalink -

https://repository.uel.ac.uk/item/8607y

Log in to edit

  • 139
    total views
  • 0
    total downloads
  • 1
    views this month
  • 0
    downloads this month

Export as

Related outputs

Simple and effective method for the extraction of silymarin from Silybum marianum (L.) gaertner seeds
Gilabadi, S., Stanyon, H., Brandao De Ceita, D., Pendry, B. A. and Galante, E. 2023. Simple and effective method for the extraction of silymarin from Silybum marianum (L.) gaertner seeds. Journal of Herbal Medicine. 37 (Art.100619). https://doi.org/10.1016/j.hermed.2022.100619
Cranberry (Vaccinium macrocarpon) as a prophylaxis for urinary tract infections in women: A systematic review with meta-analysis
Valente, J., Pendry, B. and Galante, E. 2022. Cranberry (Vaccinium macrocarpon) as a prophylaxis for urinary tract infections in women: A systematic review with meta-analysis. Journal of Herbal Medicine. 36 (Art. 100602). https://doi.org/10.1016/j.hermed.2022.100602
Novel nucleotide–calixarene conjugates via phosphoester linkage
Consoli, Grazia M.L., Granata, Giuseppe, Galante, E., Cunsolo, Francesca and Geraci, Corrada 2006. Novel nucleotide–calixarene conjugates via phosphoester linkage. Tetrahedron Letters. 47 (19), pp. 3245-3249. https://doi.org/10.1016/j.tetlet.2006.03.043
Hydroxycinnamic acid clustered by a calixarene platform: radical scavenging and antioxidant activity
Consoli, Grazia M.L., Galante, E., Daquino, Carmelo, Granata, Giuseppe, Cunsolo, Francesca and Geraci, Corrada 2006. Hydroxycinnamic acid clustered by a calixarene platform: radical scavenging and antioxidant activity. Tetrahedron Letters. 47 (37), pp. 6611-6614. https://doi.org/10.1016/j.tetlet.2006.07.021
Synthesis of water-soluble nucleotide-calixarene conjugates and preliminary investigation of their in vitro DNA replication inhibitory activity
Consoli, Grazia M.L., Granata, Giuseppe, Galante, E., Di Silvestro, Isabella, Salafia, Laura and Geraci, Corrada 2007. Synthesis of water-soluble nucleotide-calixarene conjugates and preliminary investigation of their in vitro DNA replication inhibitory activity. Tetrahedron. 63 (44), pp. 10758-10763. https://doi.org/10.1016/j.tet.2007.06.123
Calix[4]arene Decorated with Four Tn Antigen Glycomimetic Units and P3CS Immunoadjuvant: Synthesis, Characterization, and Anticancer Immunological Evaluation
Geraci, Corrada, Consoli, Grazia M. L., Galante, E., Bousquet, Ennio, Pappalardo, Maria and Spadaro, Angelo 2008. Calix[4]arene Decorated with Four Tn Antigen Glycomimetic Units and P3CS Immunoadjuvant: Synthesis, Characterization, and Anticancer Immunological Evaluation. Bioconjugate Chemistry. 19 (3), pp. 751-758. https://doi.org/10.1021/bc700411w
A sinapic acid–calix[4]arene hybrid selectively binds Pb2+ over Hg2+ and Cd2+
Sgarlata, Carmelo, Zito, Valeria, Arena, Giuseppe, Consoli, Grazia Maria Letizia, Galante, E. and Geraci, Corrada 2009. A sinapic acid–calix[4]arene hybrid selectively binds Pb2+ over Hg2+ and Cd2+. Polyhedron. 28 (2), pp. 343-348. https://doi.org/10.1016/j.poly.2008.10.068
A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of125I-Labeled Molecular Probes
Yan, Ran, Sander, Kerstin, Galante, E., Rajkumar, Vineeth, Badar, Adam, Robson, Mathew, El-Emir, Ethaar, Lythgoe, Mark F., Pedley, R. Barbara and Årstad, Erik 2012. A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of125I-Labeled Molecular Probes. Journal of the American Chemical Society. 135 (2), pp. 703-709. https://doi.org/10.1021/ja307926g
First Self-Adjuvant Multicomponent Potential Vaccine Candidates by Tethering of Four or Eight MUC1 Antigenic Immunodominant PDTRP Units on a Calixarene Platform: Synthesis and Biological Evaluation
Geraci, Corrada, Consoli, Grazia M. L., Granata, Giuseppe, Galante, E., Palmigiano, Angelo, Pappalardo, Maria, Di Puma, Salvatore D. and Spadaro, Angelo 2013. First Self-Adjuvant Multicomponent Potential Vaccine Candidates by Tethering of Four or Eight MUC1 Antigenic Immunodominant PDTRP Units on a Calixarene Platform: Synthesis and Biological Evaluation. Bioconjugate Chemistry. 24 (10), pp. 1710-1720. https://doi.org/10.1021/bc400242y
Development of Purine-Derived18F-Labeled Pro-drug Tracers for Imaging of MRP1 Activity with PET
Galante, E., Okamura, Toshimitsu, Sande, Kerstin, Kikuchi, Tatsuya, Okada, Maki, Zhang, Ming-Rong, Robson, Mathew, Badar, Adam, Lythgoe, Mark, Koepp, Matthias and Årstad, Erik 2014. Development of Purine-Derived18F-Labeled Pro-drug Tracers for Imaging of MRP1 Activity with PET. Journal of Medicinal Chemistry. 57 (3), pp. 1023-1032. https://doi.org/10.1021/jm401764a
Silymarin content in Silybum marianum extracts as a biomarker for the quality of commercial tinctures
Pendry, B., Kemp, Virginia, Hughes, Michael J., Freeman, Julia, Nuhu, Hanny K., Sanchez-Medina, Alberto, Corcoran, O. and Galante, E. 2017. Silymarin content in Silybum marianum extracts as a biomarker for the quality of commercial tinctures. Journal of Herbal Medicine. 10, pp. 31-36. https://doi.org/10.1016/j.hermed.2017.07.001
Preferential Targeting of Disseminated Liver Tumors Using a Recombinant Adeno-Associated Viral Vector
Della Peruta, Marco, Badar, Adam, Rosales, Cecilia, Chokshi, Shilpa, Kia, Azadeh, Nathwani, Devhrut, Galante, E., Yan, Ran, Arstad, Erik, Davidoff, Andrew M., Williams, Roger, Lythgoe, Mark F. and Nathwani, Amit C. 2015. Preferential Targeting of Disseminated Liver Tumors Using a Recombinant Adeno-Associated Viral Vector. Human Gene Therapy. 26 (2), pp. 94-103. https://doi.org/10.1089/hum.2014.052
Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography
Sander, K., Galante, E., Gendron, T., Yiannaki, E., Patel, N., Kalber, T. L., Badar, A., Robson, M., Johnson, S. P., Bauer, F., Mairinger, S., Stanek, J., Wanek, T., Kuntner, C., Kottke, T., Weizel, L., Dickens, D., Erlandsson, K., Hutton, B. F., Lythgoe, M. F., Stark, H., Langer, O., Koepp, M. and Årstad, E. 2015. Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography. Journal of Medicinal Chemistry. 58 (15), pp. 6058-6080. https://doi.org/10.1021/acs.jmedchem.5b00652
Chelator-Accelerated One-Pot ‘Click’ Labeling of Small Molecule Tracers with 2-[18F]Fluoroethyl Azide
Galante, E., Schoultz, Bent, Koepp, Matthias and Årstad, Erik 2013. Chelator-Accelerated One-Pot ‘Click’ Labeling of Small Molecule Tracers with 2-[18F]Fluoroethyl Azide. Molecules. 18 (5), pp. 5335-5347. https://doi.org/10.3390/molecules18055335