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Radiolabeled novel peptide for imaging somatostatin-receptor expressing tumor: synthesis and radiobiological evaluation

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Abstract

The aim of this study was to synthesis, a radiolabeled (99mTc) new somatostatin-analogue 6-hydrazinopyridine-3-carboxylic-acid (HYNIC)-Asn3-octreotate (99mTc-HYNIC-AATE), and to evaluate as a candidate for imaging somatostatin-receptor (SSTR)-positive tumors and also compare it with 99mTc-HYNIC-Tyr3-octreotide (99mTc-HYNIC-TOC). Synthesis was performed by Fmoc-solid-phase strategy and 99mTc labeled by SnCl2. Biodistribution and imaging properties of new radiopeptide were also studied in C6 tumor bearing rat. Radiolabeling was performed at high specific activities and it showed high binding-affinity for SSTR2. In biodistribution, radiopeptides have showed high and receptor-specific uptake in the SSTR2 positive organs, tumor with rapid renal excretion from non-target tissues. These results demonstrated that 99mTc-HYNIC-AATE is a new specific radioligand for scintigraphy of somatostatin-receptor-positive tumors.

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References

  1. Lamberts SW, Krenning EP, Reubi JC (1991) Endocr Rev 12:450–482

    Article  CAS  Google Scholar 

  2. Arnold R, Simon B, Wied M (2000) Digestion 62:84–91

    Article  CAS  Google Scholar 

  3. Liu S, Edwards DS (1999) Chem Rev 99:2235–2268

    Article  CAS  Google Scholar 

  4. Susini C, Buscail L (2006) Ann Oncol 17:1733–1742

    Article  CAS  Google Scholar 

  5. Kwekkeboom DJ, Krenning EP (2002) Semin Nucl Med 32:84–89

    Article  Google Scholar 

  6. Koenig JA, Edwardson JM, Humphrey PPA (1997) Br J Pharmacol 120:45–51

    CAS  Google Scholar 

  7. Breeman WAP, Jong M, Kwekkeboom DJ, Valkema R, Bakker WH, Kooij PPM, Visser TJ, Krenning EP (2001) Eur J Nucl Med 28:1421–1429

    Article  CAS  Google Scholar 

  8. Gandomkar M, Naijafi R, Shafiei M, Mazidi M, Ebrahimi SES (2007) Nucl Med Biol 34:651–657

    Article  CAS  Google Scholar 

  9. Akizawa H, Arano Y, Mifune M, Iwado A, Saito Y, Mukai T, Uehara T, Ono M, Fujioka Y, Ogawa K, Kiso Y, Saji H (2001) Nucl Med Biol 28:761–768

    Article  CAS  Google Scholar 

  10. Reubi JC, Schai JC, Waser B, Wenger S, Heppeler A, Schmit JS (2000) Eur J Nucl Med 27:273–282

    Article  CAS  Google Scholar 

  11. Kopecky M, Semecky V, Trejtnar F, Laznicek M, Laznickova A, Nachtigal P (2004) Nucl Med Biol 31:231–239

    Article  CAS  Google Scholar 

  12. Babich JW, Fischman AJ (1995) Nucl Med Biol 22:25–30

    Article  CAS  Google Scholar 

  13. Decristoforo C, Melendez-Alafort L, Sosabowski JK, Mather SJ (2000) J Nucl Med 41:1114–1119

    CAS  Google Scholar 

  14. Okarvi SM (2004) Med Res Rev 24:357–397

    Article  CAS  Google Scholar 

  15. Van Den Bossche B, Van de Wiele C (2004) J Clin Oncol 22:3593–3607

    Article  Google Scholar 

  16. Vaidyanathan G, Friedman HS, Affleck DJ, Schottelius M, Wester H, Zalutsky MR (2003) Clin Cancer Res 9:1868–1876

    CAS  Google Scholar 

  17. Lee TW, Chang SR, Chen ST, Tsai ZT (1998) Appl Radiat Isot 49:1581–1586

    Article  CAS  Google Scholar 

  18. Storch D, Behe M, Walter MA, Chen J, Powell P, Mikolajczak R, Mäcke RH (2005) J Nucl Med 46:1561–1569

    CAS  Google Scholar 

  19. Guggenberg EV, Penz B, Kemmler G, Virgolini I, Decristoforo C (2006) Appl Radiat Isot 64:194–200

    Article  Google Scholar 

  20. Behera A, De K, Chandra S (2011) J Radioanal Nucl Chem 290:123–129

    Article  CAS  Google Scholar 

  21. Hanaoka H, Tominaga H, Yamada K, Paudyal P, Iida Y, Watanabe S, Paudyal B, Higuchi T, Oriuchi N, Endo K (2009) Ann Nucl Med 23:559–567

    Article  CAS  Google Scholar 

  22. De K, Chandra S, Sarkar B, Ganguly S, Misra M (2010) J Radioanal Nucl Chem 283:621–628

    Article  CAS  Google Scholar 

  23. Nikolopoulou A, Maina T, Sotiriou P, Cordopatis P, Nock AB (2006) J Pept Sci 12:124–131

    Article  CAS  Google Scholar 

  24. Maina T, Nock AB, Cordopatis P, Bernard FB, Breeman PAW, Gameren AV, Van den Berg RVD, Reubi CJ, Krenning EP, de Jong M (2006) Eur J Nucl Med Mol Imaging 33:831–840

    Article  Google Scholar 

  25. Lamszus K, Meverhof W, Westpha M (1997) J Neurooncol 35:353–364

    Article  CAS  Google Scholar 

  26. Parsa AT, Chakrabarti I, Hurley PT, Chi JH, Hall JS, Kaiser MG, Bruce JN (2000) Neurosurgery 47:993–999

    Article  CAS  Google Scholar 

  27. Guevara P, Sotelo J (1999) J Neurooncol 44:91–92

    Article  CAS  Google Scholar 

  28. Li WP, Lewis JS, Kim J, Bugaj JE, Johnson MA, Erion JL, Anderson CJ (2002) Bioconjug Chem 13:721–728

    Article  CAS  Google Scholar 

  29. Decristoforo C, Mather JS (1999) Bioconjug Chem 19:431–438

    Article  Google Scholar 

  30. Held-Feindt J, Krisch B, Forstreuter F, Mentlein R (2000) J Physiol Paris 2000(94):251–258

    Article  Google Scholar 

  31. Zhang H, Moroz AM, Serganova I, Ku T, Huang R, Vider J, Helmut R, Maecke HR, Larson SM, Blasberg R, Smith-Jones MP (2011) J Nucl Med 52:123–131

    Article  CAS  Google Scholar 

  32. de Jong M, Bakker WH, Breeman PAW, Bernard FB, Hofland JL, Srinivasan JT, Schmidt M, Behe M, Maecke H, Krenning PE (1998) Int J Cancer 75:406–411

    Article  Google Scholar 

  33. Lewis SJ, Lewis RM, Srinivasan A, Schmidt AM, Wang J, Anderson JC (1999) J Med Chem 42:1341–1347

    Article  CAS  Google Scholar 

  34. Nikolopoulou A, Nock B, Mania AT (2006) Anticancer Res 26:363–366

    CAS  Google Scholar 

  35. Bangard M, Behe M, Guhlke S, Otte SR, Bender H, Maecke RH, Biersack JH (2000) Eur J Nucl Med 27:628–637

    Article  CAS  Google Scholar 

  36. Weiner RE, Thakur ML (2002) Appl Radiat Isot 57:749–763

    Article  CAS  Google Scholar 

  37. Laznickova A, Laznicek M, Trejtnar F, Melicharova L, Suzuki KH, Akizawa H, Arano Y, Yokoyama A (2002) Eur J Drug Metab Pharmacokin 27:37–43

    Article  CAS  Google Scholar 

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Acknowledgments

Financial support in the form of Research Associateship (Dr. Kakali De) from the Indian Council of Medical Research (ICMR), New Delhi, India, is acknowledged. The authors also gratefully acknowledge Prof. Siddhartha Roy, Director, CSIR-Indian Institute of Chemical Biology, Kolkata, India for infrastructure support of this work.

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Authors and Affiliations

  1. Department of Infectious Diseases and Immunology (Nuclear Medicine Division), Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Biology (IICB), 4 Raja S C Mullick Road, Kolkata, 700032, West Bengal, India

    Kakali De, Asoke Behera, Indranil Banerjee & Mridula Misra

  2. Regional Radiation Medicine Centre, Variable Energy Cyclotron Centre, Kolkata, West Bengal, India

    Bharat Sarkar & Santanu Ganguly

Authors
  1. Kakali De
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  2. Asoke Behera
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  3. Indranil Banerjee
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  4. Bharat Sarkar
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  5. Santanu Ganguly
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  6. Mridula Misra
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Corresponding authors

Correspondence to Kakali De or Mridula Misra.

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De, K., Behera, A., Banerjee, I. et al. Radiolabeled novel peptide for imaging somatostatin-receptor expressing tumor: synthesis and radiobiological evaluation. J Radioanal Nucl Chem 301, 847–861 (2014). https://doi.org/10.1007/s10967-014-3199-6

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  • DOI: https://doi.org/10.1007/s10967-014-3199-6

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