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BioMed Research International
Volume 2015, Article ID 284354, 12 pages
http://dx.doi.org/10.1155/2015/284354
Research Article

Synthesis, 68Ga-Radiolabeling, and Preliminary In Vivo Assessment of a Depsipeptide-Derived Compound as a Potential PET/CT Infection Imaging Agent

1Department of Nuclear Medicine, University of Pretoria & Steve Biko Academic Hospital, Corner Malherbe and Steve Biko Road, Pretoria 0001, South Africa
2School of Chemistry and Physics, Westville Campus, University Road, Westville, Durban 3630, South Africa
3School of Health Sciences, Catalysis and Peptide Research Unit, E-Block 6th Floor, Westville Campus, University Road, Westville, Durban 3630, South Africa
4Department of Virology, University of KwaZulu-Natal, National Health Laboratory Service, P.O. Box 1900, Westville, Durban 3630, South Africa
5Division of PET Imaging & Radiochemistry, Molecular Imaging Research Centre, INMAS, Brig S. K. Mazumdar Marg, Timarpur, Delhi 110054, India
6Radiochemistry Section Necsa, Building P1600, Pelindaba, Brits, North West Province, South Africa
7Department of Science and Technology, Preclinical Drug Development Platform, North West University, 11 Hoffman Street, Potchefstroom 2520, South Africa

Received 7 June 2014; Revised 28 July 2014; Accepted 5 August 2014

Academic Editor: Alberto Signore

Copyright © 2015 Botshelo B. Mokaleng et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. G. Malviya and A. Sinore, “Infection and inflammation imaging,” Nuclear Medicine and Biology, vol. 41, no. 6, p. 488, 2014. View at Google Scholar
  2. A. Signore, C. Lauri, and F. Galli, “Radiolabelled probes targeting infection and inflammation for personalized medicine,” Current Pharmaceutical Design, vol. 20, no. 14, pp. 2338–2345, 2014. View at Google Scholar
  3. M. M. Welling, S. Mongera, A. Lupetti et al., “Radiochemical and biological characteristics of 99mTc-UBI 29-41 for imaging of bacterial infections,” Nuclear Medicine and Biology, vol. 29, no. 4, pp. 413–422, 2002. View at Publisher · View at Google Scholar · View at Scopus
  4. G. Ferro-Flores, F. D. M. Ramírez, L. Meléndez-Alafort, C. A. D. Murphy, and M. Pedraza-López, “Molecular recognition and stability of 99mTc-UBI 29-41 based on experimental and semiempirical results,” Applied Radiation and Isotopes, vol. 61, no. 6, pp. 1261–1268, 2004. View at Publisher · View at Google Scholar · View at Scopus
  5. T. Ebenhan, J. R. Zeevaart, J. D. Venter et al., “Preclinical evaluation of 68Ga-labeled 1, 4, 7-triazacyclononane-1, 4, 7-triacetic acid-ubiquicidin as a radioligand for PET infection imaging,” Journal of Nuclear Medicine, vol. 55, no. 2, pp. 308–314, 2014. View at Publisher · View at Google Scholar
  6. J. S. Davies, “The cyclization of peptides and depsipeptides,” Journal of Peptide Science, vol. 9, no. 8, pp. 471–501, 2003. View at Publisher · View at Google Scholar · View at Scopus
  7. V. K. Narayanaswamy, F. Albericio, Y. M. Coovadia et al., “Total synthesis of a depsidomycin analogue by convergent solid-phase peptide synthesis and macrolactonization strategy for antitubercular activity,” Journal of Peptide Science, vol. 17, no. 10, pp. 683–689, 2011. View at Publisher · View at Google Scholar · View at Scopus
  8. H. Li, B. Li, H. Song, L. Breydo, I. V. Baskakov, and L.-X. Wang, “Chemoenzymatic synthesis of HIV-1 V3 glycopeptides carrying two N-glycans and effects of glycosylation on the peptide domain,” The Journal of Organic Chemistry, vol. 70, no. 24, pp. 9990–9996, 2005. View at Publisher · View at Google Scholar · View at Scopus
  9. B. Behnam Azad, V. A. Rota, D. Breadner, S. Dhanvantari, and L. G. Luyt, “Design, synthesis and in vitro characterization of Glucagon-Like Peptide-1 derivatives for pancreatic beta cell imaging by SPECT,” Bioorganic and Medicinal Chemistry, vol. 18, no. 3, pp. 1265–1272, 2010. View at Publisher · View at Google Scholar · View at Scopus
  10. S. M. Mandal, L. Migliolo, and O. L. Franco, “The use of MALDI-TOF-MS and in Silico studies for determination of antimicrobial peptides' affinity to bacterial cells,” Journal of the American Society for Mass Spectrometry, vol. 23, no. 11, pp. 1939–1948, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. D. A. Scudiero, R. H. Shoemaker, K. D. Paull et al., “Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines,” Cancer Research, vol. 48, no. 17, pp. 4827–4833, 1988. View at Google Scholar · View at Scopus
  12. W. A. P. Breeman, M. de Jong, E. de Blois, B. F. Bernard, M. Konijnenberg, and E. P. Krenning, “Radiolabelling DOTA-peptides with 68Ga,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 32, no. 4, pp. 478–485, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. D. D. Rossouw and W. A. P. Breeman, “Scaled-up radiolabelling of DOTATATE with68Ga eluted from a SnO2-based68Ge/68Ga generator,” Applied Radiation and Isotopes, vol. 70, no. 1, pp. 171–175, 2012. View at Publisher · View at Google Scholar · View at Scopus
  14. M. Ocak, M. Antretter, R. Knopp et al., “Full automation of 68Ga labelling of DOTA-peptides including cation exchange prepurification,” Applied Radiation and Isotopes, vol. 68, no. 2, pp. 297–302, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. D. Billot-Klein, D. Shlaes, D. Bryant et al., “Presence of UDP-N-Acetylmuramyl-Hexapeptides and -Heptapeptides in enterococci and staphylococci after treatment with ramoplanin, tunicamycin, or vancomycin,” Journal of Bacteriology, vol. 179, no. 15, pp. 4684–4688, 1997. View at Google Scholar · View at Scopus
  16. I. L. Karle, D. Ranganathan, M. G. Kumar, and R. Nagaraj, “Design, synthesis, conformational and membrane ion transport studies of proline-adamantane hybrid cyclic depsipeptides,” Biopolymers, vol. 89, no. 5, pp. 471–478, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. L. Zhang, A. Rozek, and R. E. W. Hancock, “Interaction of cationic antimicrobial peptides with model membrane,” The Journal of Biological Chemistry, vol. 276, no. 21, pp. 35714–35722, 2001. View at Google Scholar · View at Scopus
  18. L. M. de León-Rodriguez, Z. Kovacs, G. R. Dieckmann, and A. D. Sherry, “Solid-phase synthesis of DOTA-peptides,” Chemistry, vol. 10, no. 5, pp. 1149–1155, 2004. View at Publisher · View at Google Scholar · View at Scopus
  19. M. S. Akhtar, M. B. Imran, M. A. Nadeem, and A. Shahid, “Antimicrobial peptides as infection imaging agents: better than radiolabeled antibiotics,” International Journal of Peptides, vol. 2012, Article ID 965238, 19 pages, 2012. View at Publisher · View at Google Scholar · View at Scopus
  20. T. Ujula, S. Salomäki, P. Virsu et al., “Synthesis, 68Ga labeling and preliminary evaluation of DOTA peptide binding vascular adhesion protein-1: a potential PET imaging agent for diagnosing osteomyelitis,” Nuclear Medicine and Biology, vol. 36, no. 6, pp. 631–641, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. L. Yang, T. M. Weiss, R. I. Lehrer, and H. W. Huang, “Crystallization of antimicrobial pores in membranes: magainin and protegrin,” Biophysical Journal, vol. 79, no. 4, pp. 2002–2009, 2000. View at Publisher · View at Google Scholar · View at Scopus
  22. H. W. Huang, “Action of antimicrobial peptides: two-state model,” Biochemistry, vol. 39, no. 29, pp. 8347–8352, 2000. View at Publisher · View at Google Scholar · View at Scopus
  23. E. de Blois, H. S. Chan, C. Naidoo, D. Prince, E. P. Krenning, and W. A. P. Breeman, “Characteristics of SnO2-based 68Ge/68Ga generator and aspects of radiolabelling DOTA-peptides,” Applied Radiation and Isotopes, vol. 69, no. 2, pp. 308–315, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. T. Ebenhan, N. Chadwick, M. M. Sathekge et al., “Peptide synthesis, characterization and 68Ga-radiolabeling of NOTA-conjugated ubiquicidin fragments for prospective infection imaging with PET/CT,” Nuclear Medicine and Biology, vol. 41, no. 5, pp. 390–400, 2014. View at Publisher · View at Google Scholar
  25. D. Mueller, I. Klette, R. P. Baum, M. Gottschaldt, M. K. Schultz, and W. A. P. Breeman, “Simplified NaCl based 68Ga concentration and labeling procedure for rapid synthesis of 68Ga radiopharmaceuticals in high radiochemical purity,” Bioconjugate Chemistry, vol. 23, no. 8, pp. 1712–1717, 2012. View at Publisher · View at Google Scholar · View at Scopus
  26. R. Lesche, G. Kettschau, A. V. Gromov et al., “Preclinical evaluation of BAY 1075553, a novel 18F-labelled inhibitor of prostate-specific membrane antigen for PET imaging of prostate cancer,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 41, no. 1, pp. 89–101, 2014. View at Publisher · View at Google Scholar · View at Scopus
  27. A. R. Jalilian, H. Yousefnia, K. Shafaii, A. Novinrouz, and A. A. Rajamand, “Preparation and biodistribution studies of a radiogallium-acetylacetonate bis (thiosemicarbazone) complex in tumor-bearing rodents,” Iranian Journal of Pharmaceutical Research, vol. 11, no. 2, pp. 523–531, 2012. View at Google Scholar · View at Scopus
  28. B. Y. Yang, J. M. Jeong, Y. J. Kim et al., “Formulation of 68Ga BAPEN kit for myocardial positron emission tomography imaging and biodistribution study,” Nuclear Medicine and Biology, vol. 37, no. 2, pp. 149–155, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. A. Fontes, M. I. M. Prata, C. F. Geraldes, and J. P. André, “Ga(III) chelates of amphiphilic DOTA-based ligands: synthetic route and in vitro and in vivo studies,” Nuclear Medicine and Biology, vol. 38, no. 3, pp. 363–370, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. T. Ebenhan, O. Gheysens, G. E. M. Maguire et al., “[68Ga]NOTA-UBI-PET: a host-independent targeted method to non-invasively imaging of bacterial infection-preclinical evaluation in small animal models,” (WFNMB accepted abstract publication), 2014.
  31. M. S. Akhtar, J. Iqbal, M. A. Khan et al., “99mTc-labeled antimicrobial peptide ubiquicidin (29–41) accumulates less in Escherichia coli infection than in Staphlococcus aureus infection,” Journal of Nuclear Medicine, vol. 45, no. 5, pp. 849–856, 2004. View at Google Scholar · View at Scopus
  32. J. Silvola, A. Autio, P. Luoto, S. Jalkanen, and A. Roivainen, “Preliminary evaluation of novel 68Ga-DOTAVAP-PEG-P2 peptide targeting vascular adhesion protein-1,” Clinical Physiology and Functional Imaging, vol. 30, no. 1, pp. 75–78, 2010. View at Publisher · View at Google Scholar · View at Scopus
  33. L. Hoigebazar, J. M. Jeong, M. K. Hong et al., “Synthesis of 68Ga-labeled DOTA-nitroimidazole derivatives and their feasibilities as hypoxia imaging PET tracers,” Bioorganic & Medicinal Chemistry, vol. 19, no. 7, pp. 2176–2181, 2011. View at Publisher · View at Google Scholar · View at Scopus
  34. C. Cocito, M. Di Giambattista, E. Nyssen, and P. Vannuffel, “Inhibition of protein synthesis by streptogramins and related antibiotics,” The Journal of Antimicrobial Chemotherapy, vol. 39, supplement 1, pp. 7–13, 1997. View at Publisher · View at Google Scholar · View at Scopus
  35. J.-L. Thomassin, J. R. Brannon, J. Kaiser, S. Gruenheid, and H. le Moual, “Enterohemorrhagic and enteropathogenic Escherichia coli evolved different strategies to resist antimicrobial peptides,” Gut Microbes, vol. 3, no. 6, pp. 556–561, 2012. View at Publisher · View at Google Scholar · View at Scopus
  36. J.-L. Thomassin, J. R. Brannon, B. F. Gibbs, S. Gruenheid, and H. Le Moual, “OmpT outer membrane proteases of enterohemorrhagic and enteropathogenic Escherichia coli contribute differently to the degradation of human LL-37,” Infection and Immunity, vol. 80, no. 2, pp. 483–492, 2012. View at Publisher · View at Google Scholar · View at Scopus
  37. B. Sperandio, B. Regnault, J. Guo et al., “Virulent Shigella flexneri subverts the host innate immune response through manipulation of antimicrobial peptide gene expression,” The Journal of Experimental Medicine, vol. 205, no. 5, pp. 1121–1132, 2008. View at Publisher · View at Google Scholar · View at Scopus
  38. D. Islam, L. Bandholtz, J. Nilsson et al., “Downregulation of bactericidal peptides in enteric infections: a novel immune escape mechanism with bacterial DNA as a potential regulator,” Nature Medicine, vol. 7, no. 2, pp. 180–185, 2001. View at Publisher · View at Google Scholar · View at Scopus
  39. H. Le Moual, J.-L. Thomassin, and J. R. Brannon, “Antimicrobial peptidesas an alternative approach to treat bacterial infections,” Journal of Clinical & Cellular Immunology, vol. S13, article 004, 2013. View at Publisher · View at Google Scholar