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Radiochemistry

, Volume 60, Issue 6, pp 638–643 | Cite as

Preclinical Evaluation of Radioiodinated Quinoxaline Derivative as a Possible Brain Imaging Agent

  • I. T. Ibrahim
  • H. M. Talaat
  • R. A. Ayad
  • K. Farah
Article

Abstract

4-{(4-Methylphenyl)glycyl}-3,4-dihydroquinoxalin-2(1H)-one (QIN) was prepared from 4-(2-chloroacetyl)- 3,4-dihydroquinoxalin-1(1H)-one). 125I-QIN was prepared by electrophilic substitution using Chloramine- T as an oxidizing agent. The highest labeling yield, 94%, was obtained under the following conditions: pH 7, 15 min, 100 μg of QIN, 50 μg of Chloramine-T, and carrier-free Na125I. The labeled compound was stable for up to 12 h post labeling. A biodistribution study of 125I-QIN in mice showed that its brain uptake was about 5.1% at 30 min post injection and remained on this level up to 1 h. As compared to commercially used radiopharmaceuticals for brain imaging, 125I-QIN is more stable and shows higher brain uptake.

Keywords

quinoxaline derivatives iodine-125 radiochemical yield imaging brain 

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References

  1. 1.
    Determination of Organic Structures by Physical Methods, Braude, E.A., and Nachod, F.C., Eds., New York: Academic, 1955.Google Scholar
  2. 2.
    Wu, X.-H. Liu, G., et al., Mol. Diver., 2004, vol. 8, no. 2, pp. 165–147.CrossRefGoogle Scholar
  3. 3.
    Renault, J., Baron, M., Mailliet, P., et al., Eur. J. Med. Chem., 1981, vol. 16, no. 6, pp. 545–550.Google Scholar
  4. 4.
    Wu, X.-H., Gorden, A.E.V., et al., J. Org. Chem., 2007, vol. 72, no. 23, pp. 8691–8699.CrossRefGoogle Scholar
  5. 5.
    Heravi, M.M., Bakhtiari, K., Tehrani, M.H., et al., Arkivoc, 2006, vol. 2006, no. 16, pp. 16–22.CrossRefGoogle Scholar
  6. 6.
    Chen, B., Su, B., and Chen, S., Biochem. Pharmacol., 2009, vol. 77, no. 12, pp. 1787–1794.CrossRefGoogle Scholar
  7. 7.
    Greenhough, A., Smartt, H.J.M., Moore, A.E., et al., Carcinogenesis, 2009, vol. 30, no. 3, pp. 377–386.CrossRefGoogle Scholar
  8. 8.
    Ameen, A.A.-H., Am. J. Org. Chem., 2015, vol. 5, no. 1, pp. 14–56.Google Scholar
  9. 9.
    Wally, M.A., El-Gogray, S.R., and El-Sepelgy, O.Z., Synth. Commun., 2010, vol. 40, pp. 1–5.Google Scholar
  10. 10.
    Ganapathy, S., Ramalingam, P. and Babu Rao, C.H., Indian J. Heterocycl. Chem., 2007, vol. 16, pp. 283–286.Google Scholar
  11. 11.
    Husain, A., Rashid, M., Akhter, A., and Mishra, R., J. Pharm. Res., 2011, vol. 4, no. 3, pp. 888–890.Google Scholar
  12. 12.
    Abu-Hashem, A.A., Gouda, M.A., and Badria, F.A., Eur. J. Med. Chem., 2010, vol. 45, pp. 1976–1981.CrossRefGoogle Scholar
  13. 13.
    Carta, A., Corona, P. and Loriga, M., Curr. Med. Chem., 2005, vol. 12, pp. 2259–2272.CrossRefGoogle Scholar
  14. 14.
    Gali-Muhtasib, H.U., Haddadin, M.J., Rahhal, D.N. and Younes, I.H., Oncol. Rep., 2001, vol. 8, pp. 679–684.Google Scholar
  15. 15.
    Al-Mutairi, F.M., Abdel-Daim, M.M., Ibrahim, I.T., et al., Int. J. Pharm. Res. Allied Sci., 2016, vol. 5, no. 1, pp. 203–218.Google Scholar
  16. 16.
    Burguete, A., Pontiki, E., Hadjipavlou-Litina, D., et al., Bioorg. Med. Chem. Lett., 2007, vol. 17, pp. 6439–6443.CrossRefGoogle Scholar
  17. 17.
    Brown, J.M. and Koong, A.J., J. Nat. Cancer Inst., 1999, vol. 83, pp. 178–185.CrossRefGoogle Scholar
  18. 18.
    Ibrahim, I.T. and Wally, M.A., J. Radioanal. Nucl. Chem., 2009, vol. 285, pp. 169–175.CrossRefGoogle Scholar
  19. 19.
    Habib, S.A., Ibrahim, I.T., Abd-Eldaye, M.A., et al., Nat. Sci., 2012, vol. 4, no. 12, pp. 1074–1084.Google Scholar
  20. 20.
    Sreekanth, N., Rao, C. and Mukkanti, K., Int. J. Pharm. Pharm. Sci., 2009, vol. 1, no. 1, pp. 186–192.Google Scholar
  21. 21.
    William, W., Orrison, J., Lewine, J., et al., Functional Brain Imaging, Salt Lake City, 1995, pp. 187–212.Google Scholar
  22. 22.
    Kónya, J. and Nagy, N., Nuclear and Radiochemistry, London: Elsevier, 2012, pp. 177–231.Google Scholar
  23. 23.
    Mohammad, A.K. and Abolfazl, H., Iran J. Org. Chem., 2009, vol. 4, pp. 268–270.Google Scholar
  24. 24.
    Abolfazl, H., Mohammad, A.K., Masoumeh, H., and Mahmoud, T.A., Monatsh. Chem., 2012, vol. 143, pp. 619–623.CrossRefGoogle Scholar
  25. 25.
    Moerlein, S.M., Beer, W., and Stocklin, G., J. Chem. Soc., Perkin Trans. 1, 1988, pp. 779–786.Google Scholar
  26. 26.
    Ibrahim, M.-K., Abd-Elrahman, A.A., Ayyad, R.R.A., et al., Bull. Faculty Pharm., Cairo Univ., 2013, vol. 51, pp. 101–111.CrossRefGoogle Scholar
  27. 27.
    Wilbur, D.S., Bioconjug. Chem., 1992, vol. 3, pp. 433–470.CrossRefGoogle Scholar
  28. 28.
    Amartey, J.K., Esguerra, C., Al-Otaibi, B., et al., Appl. Radiat. Isot., 2005, vol. 62, no. 1, pp. 39–47.CrossRefGoogle Scholar
  29. 29.
    Bapat, K., Chintalwar, G., Pandey, U., et al., Appl. Radiat. Isot., 2005, vol. 62, no. 3, pp. 389–393.CrossRefGoogle Scholar
  30. 30.
    Sadri, K., Gandomkar, M., Babaei, M.H., et al., J. Label. Compd. Radiopharm., 2009, vol. 52, pp. 289–294.CrossRefGoogle Scholar
  31. 31.
    Amin, A.M., Soliman, S.E., and El-Aziz, H.A., J. Label. Compd. Radiopharm., 2010, vol. 53, pp. 1–5.Google Scholar
  32. 32.
    Abdel-Bary, H.M., Moustafa, K.A., Abdel-Ghaney, I.Y., et al., J. Radioanal. Nucl. Chem., 2013, vol. 298, pp. 9–18.CrossRefGoogle Scholar
  33. 33.
    Jackson, P.F., Davenport, T.W., Resch, J.F., et al., Bioorg. Med. Chem. Lett., 1991, vol. 1, pp. 751–756.CrossRefGoogle Scholar
  34. 34.
    Wagle, S., Adhikari, A.V., and Kumari, N.S., Eur. J. Med. Chem., 2009, vol. 44, pp. 1135–1143.CrossRefGoogle Scholar
  35. 35.
    Motaleb, M.A., Ibrahim, I.T., Ayoub, V.R., and Geneidi, A.S., J. Label. Compd. Radiopharm., 2016, vol. 59, pp. 147–152.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2018

Authors and Affiliations

  • I. T. Ibrahim
    • 1
    • 2
  • H. M. Talaat
    • 1
  • R. A. Ayad
    • 3
    • 4
  • K. Farah
    • 1
  1. 1.Labeled Compounds Department, Hot Laboratories CenterAtomic Energy AuthorityCairoEgypt
  2. 2.Faculty of PharmacyAlbayan UniversityBaghdadIraq
  3. 3.Department of Pharmaceutical Chemistry, Faculty of PharmacyEl Azhar UniversityCairoEgypt
  4. 4.Department of Pharmaceutical Chemistry, Faculty of PharmacyDelta University for Science and TechnologyMansouraEgypt

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