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Synthesis, radiolabeling and biological distribution of a new dioxime derivative as a potential tumor imaging agent

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Abstract

A novel dioxime derivative (2E,2′E,3E,3′E)-3,3′-(pyrimidine-4,5-diylbis(azanylylidene))bis(butan-2-one)dioxime was synthesized with a yield of 65%. IR, elemental analysis, mass spectroscopy and 1H-NMR were used to characterize the structure of the synthesized compound. 99mTc-dioxime was radio-synthesized with a high radiochemical yield of 97.8 ± 0.5% and in vitro stability of 6 h under the optimum conditions. The preclinical evaluation of 99mTc-dioxime in solid tumor-bearing mice showed high accumulation in solid tumor cells with a high Target/Non-Target ratio of 5.14 at 30 min post-injection. This study suggests that 99mTc-dioxime derivative is a promising candidate as a new 99mTc-based tumor-imaging agent after further preclinical studies.

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References

  1. Gavhane YN, Shete AS, Bhagat AK, Shinde VR, Bhong KK, Khairnar GA, Yadav AV (2011) Int J Pharma Sci Res 2:1–12

    Google Scholar 

  2. Mohan H (2002) Text book of pathology, 4th edn. Jaypee Publications, New Delhi

    Google Scholar 

  3. Faulkner S, Long N (2011) Dalton Trans 23:6057

    Google Scholar 

  4. Sakr TM, Essa BM, El-Essawy FA, El-Mohty AA (2014) Radiochemistry 56:76–80

    Article  CAS  Google Scholar 

  5. Reichert DE, Lewis JS, Anderson CJ (1999) Coord Chem Rev 184:3–66

    Article  CAS  Google Scholar 

  6. Méndez-Rojas MA, Kharisov BI, Tsivadze AY (2006) J Coord Chem 59:1–63

    Article  Google Scholar 

  7. Essa BM, Sakr TM, Khedr AM, El-Essawy FA, El-Mohty AA (2015) Eur J Pharm Sci 76:102–109

    Article  CAS  Google Scholar 

  8. Abrantes AM, Serra ME, Gonçalves AC, Rio J, Oliveiros B, Laranjo M, Rocha-Gonsalves AM, Sarmento-Ribeiro AB, Botelho MF (2010) Nucl Med Biol 37:125–132

    Article  CAS  Google Scholar 

  9. Sun X, Chu T, Wang X (2010) Nucl Med Biol 37:117–123

    Article  CAS  Google Scholar 

  10. Engelhardt EL, Schneider RF, Seeholzer SH, Stobbe CC, Chapman JD (2002) J Nucl Med 43:835–850

    Google Scholar 

  11. Riché F, d’Hardemare AD, Sèpe S, Riou L, Fagret D, Vidal M (2001) Bioorg Med Chem Lett 11:71–74

    Article  Google Scholar 

  12. Wan W, Yang M, Pan S, Yu C, Wu N (2008) Drug Dev Res 69:520–525

    Article  CAS  Google Scholar 

  13. Wang J, Yang J, Yan Z, Duan X, Tan C, Shen Y, Wu W (2011) J Radioanal Nucl Chem 287:465–469

    Article  CAS  Google Scholar 

  14. Mallia MB, Subramanian S, Mathur A, Sarma HD, Venkatesh M, Banerjee S (2010) J Label Compd Radiopharm 53:535–542

    Article  CAS  Google Scholar 

  15. Ballinger JR, Kee JWM, Rauth AM (1996) J Nucl Med 37:1023–1031

    CAS  Google Scholar 

  16. Huang H, Zhou H, Li Z, Wang X, Chu T (2012) Bioorg Med Chem Lett 22:172–177

    Article  CAS  Google Scholar 

  17. Hsia CC, Huang FL, Hung GU, Shen LH, Chen CL, Wang HE (2011) Appl Radiat Isot 69:649–655

    Article  CAS  Google Scholar 

  18. Satpati D, Korde A, Venkatesh M, Banerjee S (2009) Appl Radiat Isot 67:1644–1649

    Article  CAS  Google Scholar 

  19. Sakr TM, El-Safoury DM, Awad GAS, Motaleb MA (2013) J Label Compd Radiopharm 56:392–395

    Article  CAS  Google Scholar 

  20. Kaur N, Aggarwal AK, Sharma N, Choudhary B (2012) Int J Pharm Sci Drug Res 4:199–204

    CAS  Google Scholar 

  21. Goudgaon NM, Reddy RV (2014) Int J Pharm Chem Biol Sci 4:64–68

    Google Scholar 

  22. David VB, Babu VH, Reddy VM (2014) Int J Pharm Chem Res 3:2278–8700

    Google Scholar 

  23. Goudar V, Rashmi P, Shantharam U, Hazra K, Nargund LG (2012) J Chem Pharm Res 4:3100–3106

    CAS  Google Scholar 

  24. Siddiqui AB, Trivedi AR, Kataria VB, Shah VH (2014) Bioorg Med Chem Lett 15:1493–1495

    Article  Google Scholar 

  25. Himaja M, Rout PK, Karigar AA, Poppy D, Munirajashekhar D (2012) Univ J Pharm 01:72–77

    Google Scholar 

  26. Ishak CY, Metwally NH, Wahbi HI (2013) Int J Pharm Phytopharmacol 2:407–411

    Google Scholar 

  27. Tichy M, Pohl R, Xu HY, Chen Y, Yokokawa F, Shi P et al (2012) Bioorg Med Chem 20:6123–6133

    Article  CAS  Google Scholar 

  28. Shakya N, Vedi S, Liang C, Yang F, Agrawal B, Kumar R et al (2014) Bioorg Med Chem Lett 24:1407–1409

    Article  CAS  Google Scholar 

  29. Guo D, Zhang X, Wang R, Zhou Y, Li Z, Xu J et al (2012) Bioorg Med Chem Lett 22:7114–7118

    Article  CAS  Google Scholar 

  30. Mizuhara T, Oishi S, Ohno H, Shimura K, Matsuoka M, Fujii N (2012) Bioorg Med Chem 20:6434–6441

    Article  CAS  Google Scholar 

  31. Rai SU, Isloor AM, Shetty P, Pal KS, Fun HK (2014) Arabian J Chem 8:317–3121

    Google Scholar 

  32. Verma AK, Kumari R, Sing AK, Sharma BB, Martin A, Kant R (2014) Int Res J Pharm 5:922

    Article  CAS  Google Scholar 

  33. Fathalla OA, Zeid F, Haiba ME, Soliman M, Abd-Elmoez HI, El-Serwy WS (2009) World J Chem 4:127–132

    CAS  Google Scholar 

  34. Mane UR, Li H, Huang J, Gupta RC, Nadkarni SS, Giridha R et al (2012) Bioorg Med Chem Lett 20:6296–6304

    Article  CAS  Google Scholar 

  35. Morgan J, Haritakul R, Keller PA (2008) Lett Drug Des Discov 5:277–280

    Article  CAS  Google Scholar 

  36. Qin W, Sang C, Zhang L, Wei W, Tian H, Liu H et al (2015) Eur J Med Chem 95:174–184

    Article  CAS  Google Scholar 

  37. Motaleb MA, Sakr TM (2011) J Label Compd Radiopharm 54:597–601

    Article  CAS  Google Scholar 

  38. Motaleb MA (2007) J Radioanal Nucl Chem 272:95–99

    Article  CAS  Google Scholar 

  39. Hall AV, Solanki KK, Vinjamuri S, Britton KE, Das SS (1998) J Clin Pathol 51:215–219

    Article  CAS  Google Scholar 

  40. Rhodes BA (1974) Semin Nucl Med 4:281–293

    Article  CAS  Google Scholar 

  41. Gracheva MA, Ilyushchenko ON, Kodina GE, Levin VI (1982) J Label Comp Radiopharm 19:1535

    Google Scholar 

  42. Owunwanne A, Marinsky J, Blau M (1977) J Nucl Med 18:1099–1105

    CAS  Google Scholar 

  43. Motaleb MA, Adli ASA, El-Tawoosy M, Sanad MH, AbdAllah M (2016) J. Label Compd Radiopharm 59:157–163

    Article  CAS  Google Scholar 

  44. Ding R, He Y, Xu J, Liu H, Wang X, Feng M, Qi C, Zhang J, Peng C (2012) Med Chem Res 21:523–530

    Article  CAS  Google Scholar 

  45. Zhang J, Yu Q, Huo J, Pang Y, Yang S, He Y, Tang T, Yang C, Wang X (2010) J Radioanal Nucl Chem 283:481–485

    Article  CAS  Google Scholar 

  46. Ibrahim AB, Sakr TM, Khoweysa OMA, MotalebMA Abd El-BaryA, El-Kolaly MT (2014) J Radioanal Nucl Chem 302:179–186

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Labeled Compounds Department, Hot Laboratories Center, Atomic Energy Authority, P.O. Box 13759, Cairo, Egypt

    M. A. Motaleb, Adli A. Selim, M. El-Tawoosy & M. H. Sanad

  2. Chemistry Department, Faculty of Science, Ain Shams University, Abassia, Cairo, Egypt

    M. A. El-Hashash

Authors
  1. M. A. Motaleb
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  2. Adli A. Selim
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  3. M. El-Tawoosy
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  4. M. H. Sanad
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  5. M. A. El-Hashash
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Correspondence to M. A. Motaleb.

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Motaleb, M.A., Selim, A.A., El-Tawoosy, M. et al. Synthesis, radiolabeling and biological distribution of a new dioxime derivative as a potential tumor imaging agent. J Radioanal Nucl Chem 314, 1517–1522 (2017). https://doi.org/10.1007/s10967-017-5310-2

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  • DOI: https://doi.org/10.1007/s10967-017-5310-2

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