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Journal of Radioanalytical and Nuclear Chemistry

, Volume 303, Issue 1, pp 399–406 | Cite as

Synthesis, radioiodination and in vivo evaluation of ethyl 1,4-dihydro-7-iodo-4-oxoquinoline-3-carboxylate as a potential pulmonary perfusion scintigraphic radiopharmaceutical

  • T. M. Sakr
  • M. A. Motaleb
  • W. A. Zaghary
Article

Abstract

The goal of this study was to biologically evaluate a newly synthesized radioiodinated ethyl 1,4-dihydro-7-iodo-4-oxoquinoline-3-carboxylate (EIOQC) as a potential lung scintigraphic agent. EIOQC was synthesized, characterized then radioiodinated via direct electrophilic substitution reaction. Factors affecting the radiochemical purity were studied in details and the biological distribution of the radioiodinated compound was evaluated in normal male Albino mice. EIOQC was successfully synthesized and radioiodinated with high radiochemical purity (96 ± 1.21 %) and in vitro stability up to 48 h. The biological evaluation of radioiodinated EIOQC showed high lung affinity of 21.36 ± 1.73 % injected dose/g organ (% ID/g) at 15 min. This study introduces radioiodinated EIOQC as a novel potential radiopharmaceutical for lung perfusion scintigraphy.

Keywords

Oxoquinoline radioiodination 125Lung Chloramine-T Scintigraphy 

Notes

Acknowledgments

The authors are grateful to Prof. Dr. Detlef Geffken for his help in the organic synthesis of EIOQC.

References

  1. 1.
    Soler X, Kerr KM, Marsh JJ, Renner JW, Hoh CK, Test VJ, Morris TA (2012) Respirology 17(1):180–184CrossRefGoogle Scholar
  2. 2.
    Bajc M, Neilly JB, Miniati M, Schuemichen C, Meignan M, Jonson B (2009) Eur J Nucl Med Mol Imaging 36(8):1356–1370CrossRefGoogle Scholar
  3. 3.
    Parker JA, Coleman RE, Grady E, Royal HD, Siegel BA, Stabin MG, Sostman HD, Hilson AJ (2012) J Nucl Med Technol 40(1):57–65CrossRefGoogle Scholar
  4. 4.
    Akkas BE, Gokcora N, Atasever T, Yetkin I (2011) Nucl Med Commun 32(12):1179–1184CrossRefGoogle Scholar
  5. 5.
    Yang G, Wang X, Wang Z, Jiang Y, Fu J (2011) Clin Nucl Med 36(11):1029–1030CrossRefGoogle Scholar
  6. 6.
    Gu T, Shi H, Xiu Y, Gu Y (2011) Clin Nucl Med 36(12):e209–e212CrossRefGoogle Scholar
  7. 7.
    Fazio F, Wollmer P (1981) Clin Physiol 1(4):323–337CrossRefGoogle Scholar
  8. 8.
    Mathews JJ, Maurer AH, Steiner RM, Marchetti N, Criner G, Gaughan JP, Coxson HO (2008) J Nucl Med 49(5):771–775CrossRefGoogle Scholar
  9. 9.
    Mariano-Goulart D, Barbotte E, Basurko C, Comte F, Rossi M (2006) Eur J Nucl Med Mol Imaging 33(9):1048–1054CrossRefGoogle Scholar
  10. 10.
    Ariizumi M, Tominaga S (1997) Kaku Igaku 34(9):779–787Google Scholar
  11. 11.
    Nimmo MJ, Merrick MV, Millar AM (1985) Br J Radiol 58(691):635–636CrossRefGoogle Scholar
  12. 12.
    Rowe IF, Sleight PJ, Gaunt JI, Croft DN (1984) Eur J Nucl Med 9(4):154–156CrossRefGoogle Scholar
  13. 13.
    Stavngaard T, Søgaard LV, Mortensen J, Hanson LG, Schmiedeskamp J, Berthelsen AK, Dirksen A (2005) Eur J Nucl Med Mol Imaging 32(4):448–457CrossRefGoogle Scholar
  14. 14.
    Wu Y, Kotzer CJ, Makrogiannis S, Logan GA, Haley H, Barnette MS, Sarkar SK (2011) Mol Imaging Biol 13(5):923–929CrossRefGoogle Scholar
  15. 15.
    Ogi S, Gotoh E, Uchiyama M, Fukuda K, Urashima M, Fukumitsu N (2009) Jpn J Radiol 27(1):20–24CrossRefGoogle Scholar
  16. 16.
    Kathleen PD (1998) Mosby’s diagnostic and laboratory test reference. Mosby Inc, St. LouisGoogle Scholar
  17. 17.
    Xu JH, Qin J, Chen WZ, Jiao J, Wang P, Li JF, Zhang Y, Cheng MH (2012) Clin Nucl Med 37(4):377–379CrossRefGoogle Scholar
  18. 18.
    Bartalena T, Oboldi D, Guidalotti PL, Rinaldi MF, Bertaccini P, Napoli G, Gavelli G (2008) Invest Radiol 43(6):368–373CrossRefGoogle Scholar
  19. 19.
    Klaus Z, Claudia BS, Jörg P, Joachim K (2009) Annals Nucl Med 23(1):1–16CrossRefGoogle Scholar
  20. 20.
    Vijayvergiya R, Mittal BR, Grover A, Hariram V, Bhattacharya A, Singh B (2009) Int J Cardiol 133(1):122–125CrossRefGoogle Scholar
  21. 21.
    Miroslavov AE, Gorshkov NI, Lumpov AL, Yalfimov AN, Suglobov DN, Ellis BL, Braddock R, Smith AM, Prescott MC, Lawson RS, Sharma HL (2009) Nucl Med Biol 36(1):73–79CrossRefGoogle Scholar
  22. 22.
    Lobov SA, King DW, Knox KJ, Senden TJ, Stephens RW (2013) Biomaterials 34:1732–1738CrossRefGoogle Scholar
  23. 23.
  24. 24.
    Hunt P, Frier M, Johnson AR, Berezenko S, Perkins AC (2006) Eur J Pharm Biopharm 62:26–31CrossRefGoogle Scholar
  25. 25.
    Liu FY, Shiau YC, Kao A, Hsu WH, Wang JJ, Tsai CH (2003) Nucl Med Commun 24(12):1243–1246CrossRefGoogle Scholar
  26. 26.
    Hofman MS, Beauregard JM, Barber TW, Neels OC, Eu P, Hicks RJ (2011) J Nucl Med 52(10):1513–1519CrossRefGoogle Scholar
  27. 27.
    De K, Chandra S, Sarkar B, Ganguly S, Misra M (2010) J Radioanal Nucl Chem 283:621–628CrossRefGoogle Scholar
  28. 28.
    Motaleb MA, El Kolaly MT, Rashed HM, Abd El Bary A (2012) J Radioanal Nucl Chem 292:629–635CrossRefGoogle Scholar
  29. 29.
    Sakr TM (2014) Radiochemistry 56:200–206CrossRefGoogle Scholar
  30. 30.
    Narra VR, Howell RW, Harapanhalli RS, Sastry KS, Rao DV (1992) J Nucl Med 33(12):2196–2201Google Scholar
  31. 31.
    Wang DM, Kuo JW, Kuo WT, Hsu CF, Wang MH, Chang Y, Lin WJ, Wang JT (2014) J Label Compd Radiopharm 57(3):132–135CrossRefGoogle Scholar
  32. 32.
    Ugolini C, Elisei R, Proietti A, Lupi C, Borrelli N, Viola D, Leocata P, Vitti P, Miccoli P, Toniolo A, Basolo F (2014) Thyroid 24(2):339–346CrossRefGoogle Scholar
  33. 33.
    Zhou Y, Xu X, Sun Y, Wang H, Sun H, You Q (2013) Bioorg Med Chem Lett 23(10):2974–2978CrossRefGoogle Scholar
  34. 34.
    Mitscher LA (2005) Chem Rev 105(2):559–592CrossRefGoogle Scholar
  35. 35.
    Fisher LM, Pan XS (2008) Methods Mol Med 142:11–23CrossRefGoogle Scholar
  36. 36.
  37. 37.
    De D, Byers LD, Krogstad DJ (1997) J Heterocyclic Chem 34:315–320CrossRefGoogle Scholar
  38. 38.
    De Mague D, Byers JT, Krogstad DJ (1995) Tetrahedron Lett 36:205–208CrossRefGoogle Scholar
  39. 39.
    De D, Krogstad FM, Byers LD, Krogstad DJ (1998) J Med Chem 41:4918–4926CrossRefGoogle Scholar
  40. 40.
    Greenwood N, Earnshaw A (1997) Chemistry of the elements, 2nd edn. Butterworth Heinemann, OxfordGoogle Scholar
  41. 41.
    Rhodes BA (1974) J Nucl Med 4:281Google Scholar
  42. 42.
    Mostafa M, Motaleb MA, Sakr TM (2010) Appl Radiat Isot 68:1959–1963CrossRefGoogle Scholar
  43. 43.
    Motaleb MA, Sakr TM (2011) J Label Compd Radiopharm 54:597–601CrossRefGoogle Scholar
  44. 44.
    Sakr TM, Motaleb MA, Ibrahim IT (2012) J Radioanal Nucl Chem 292:705–710CrossRefGoogle Scholar
  45. 45.
    El Azony KM (2010) J Radioanal Nucl Chem 285:315–320CrossRefGoogle Scholar
  46. 46.
    Tolmachev V, Bruskin A, Sivaev I, Lundqvist H, Sjöberg S (2002) Radiochem Acta 90:229–235CrossRefGoogle Scholar
  47. 47.
    Puttaswamy, Sukhdev A, Shubha JP (2009) J Mol Catal A Chem 310:24–33CrossRefGoogle Scholar
  48. 48.
    Puttaswamy, Vaz N (2003) Trans Met Chem 28(4):409–417CrossRefGoogle Scholar
  49. 49.
    Ramalingaiah, Jagadeesh RV, Puttaswamy (2007) J Mol Catal A Chem 265:70–79CrossRefGoogle Scholar
  50. 50.
    Motaleb MA, Moustapha ME, Ibrahim IT (2011) J Radioanal Nucl Chem 289:239–245CrossRefGoogle Scholar
  51. 51.
    Wheldon TE, O’Donoghue JA, Barrett A, Michalowski AS (1991) Radiother Oncol 21(2):91–99CrossRefGoogle Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2014

Authors and Affiliations

  1. 1.Radioactive Isotopes and Generator Department, Hot Labs CenterAtomic Energy AuthorityCairoEgypt
  2. 2.Labeled Compounds Department, Hot Labs CenterAtomic Energy AuthorityCairoEgypt
  3. 3.Pharmaceutical Chemistry Department, Faculty of PharmacyHelwan UniversityCairoEgypt

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