Development of Purine-Derived18F-Labeled Pro-drug Tracers for Imaging of MRP1 Activity with PET

Article

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
AuthorsGalante, E., Okamura, Toshimitsu, Sande, Kerstin, Kikuchi, Tatsuya, Okada, Maki, Zhang, Ming-Rong, Robson, Mathew, Badar, Adam, Lythgoe, Mark, Koepp, Matthias and Årstad, Erik
Abstract

Multidrug resistance-associated protein 1 (MRP1) is a drug efflux transporter that has been implicated in the pathology of several neurological diseases and is associated with development of multidrug resistance. To enable measurement of MRP1 function in the living brain, a series of 6-halopurines decorated with fluorinated side chains have been synthesized and evaluated as putative pro-drug tracers. The tracers were designed to undergo conjugation with glutathione within the brain and hence form the corresponding MRP1 substrate tracers in situ.
6-Bromo-7-(2-[18F]fluoroethyl)purine showed good brain uptake and rapid metabolic conversion. Dynamic PET imaging demonstrated a marked difference in brain clearance rates between wild-type and mrp1 knockout mice, suggesting that the tracer can allow noninvasive assessment of MRP1 activity in vivo.

JournalJournal of Medicinal Chemistry
Journal citation57 (3), pp. 1023-1032
ISSN0022-2623
Year2014
PublisherAmerican Chemical Society (ACS)
Digital Object Identifier (DOI)https://doi.org/10.1021/jm401764a
Web address (URL)https://doi.org/10.1021/jm401764a
Publication dates
Print23 Jan 2014
Publication process dates
Deposited18 Aug 2017
Accepted01 Jan 2014
Copyright information© 2014 American Chemical Society
Permalink -

https://repository.uel.ac.uk/item/85qx3

Log in to edit

  • 165
    total views
  • 0
    total downloads
  • 4
    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
Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity
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
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
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