Synthesis and characterization of rhenium and technetium-99m labeled insulin

Chitra Sundararajan, Travis R. Besanger, Renee Labiris, Katharina J. Guenther, Thomas Strack, Robert Garafalo, Thomas T. Kawabata, Deborah Finco-Kent, Jon Zubieta, John W. Babich, John F. Valliant

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27 Scopus citations


A 99mTc-labeled insulin analogue was synthesized through a direct labeling method in which the [99mTc(CO)3] + core was combined with a protected insulin derivative (9) bearing a M(I) chelate linked to the first amino acid of the B-chain (B1). Regioselective labeling was achieved by careful control over the pH and the reaction time. Following a TFA-anisole mediated deprotection step (decay-corrected yield of 30 ± 11%, n = 4), the identity of the final 99mTc-labeled product was confirmed by HPLC. Displacement of 125I-insulin from the insulin receptor (IR) by the Re analogue 6 was similar to that of native insulin (17.8 nM vs 11.7 nM, respectively). The extent of autophosphorylation and Akt activation, as indicated by production of phospho-Akt (pAkt), showed no statistical difference between 6 and native insulin in both assays. These results support the use of the reported 99mTc-insulin derivative as a tracer for studying insulin biochemistry in vivo

Original languageEnglish (US)
Pages (from-to)2612-2621
Number of pages10
JournalJournal of Medicinal Chemistry
Issue number6
StatePublished - Mar 25 2010

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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    Sundararajan, C., Besanger, T. R., Labiris, R., Guenther, K. J., Strack, T., Garafalo, R., Kawabata, T. T., Finco-Kent, D., Zubieta, J., Babich, J. W., & Valliant, J. F. (2010). Synthesis and characterization of rhenium and technetium-99m labeled insulin. Journal of Medicinal Chemistry, 53(6), 2612-2621.