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NODAGATOC, a New Chelator-Coupled Somatostatin Analogue Labeled with [67/68Ga] and [111In] for SPECT, PET, and Targeted Therapeutic Applications of Somatostatin Receptor (hsst2) Expressing Tumors

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Division of Radiological Chemistry, Institute of Nuclear Medicine, Department of Radiology, University Hospital, Petersgraben 4, CH-4031 Basel, Switzerland, Departamento de Bioquímica e CNC, Universidade de Coimbra, Coimbra, Portugal, Faculdade de Medicina, Serviço de Biofísica, Universidade de Coimbra, Coimbra, Portugal, and Division of Cell Biology and Experimental Cancer Research, Institute of Pathology, University of Berne, PO Box 62, Murtenstrasse 31, CH-3010 Berne, Switzerland
Cite this: Bioconjugate Chem. 2002, 13, 3, 530–541
Publication Date (Web):April 23, 2002
https://doi.org/10.1021/bc010074f
Copyright © 2002 American Chemical Society
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    Abstract

    A monoreactive NOTA (1,4,7-triazacyclononane-1,4,7-triacetic acid) derived prochelator (1-(1-carboxy-3-carbo-tert-butoxypropyl)-4,7-(carbo-tert-butoxymethyl)-1,4,7-triazacyclononane (NODAGA(tBu)3)) was synthesized in five steps with an overall yield of 21%. It is useful for the coupling to the N-terminus of peptides on solid phase and in solution; it was coupled to [Tyr3]-octreotide (TOC) on solid phase, and the resulting peptide, NODAGA-Tyr3-octreotide (NODAGATOC), was labeled with the radiometals 111In and 67Ga in high yields and good specific activities. [67Ga]− and [111In]−NODAGA-Tyr3-octreotide appear to be useful to visualize primary tumors and metastases which express somatostatin receptors subtype 2 (sstr2), such as neuroendocrine tumors, because of their high affinity to this receptor subtype with IC50 = 3.5 ± 1.6 nM and 1.7 ± 0.2 nM, respectively. NODAGATOC could be used as a SPECT and PET tracer, when labeled with 111In, 67Ga, or 68Ga, and even for therapeutic applications. Surprisingly, [111In]−NODAGATOC shows 2 times higher binding affinity to sstr2, but also a factor of 4 higher affinity to sstr5 compared to [67Ga]−NODAGATOC. [67Ga]−NODAGATOC is very stable in serum and rat liver homogenate. There is no difference in the rate of internalization into AR4-2J rat pancreatic tumor cells; both radioligands are highly internalized, at 4 h a 3 times higher uptake compared to [111In]−DOTA-Tyr3-octreotide ([111In]−DOTATOC) was found. The biodistribution of [67Ga]−NODAGATOC in AR4-2J tumor bearing nude mice is very favorable at short times after injection; there is fast excretion from all nontarget organs except the kidneys and high uptake in sst receptor rich organs and in the AR4-2J tumor. Again it is superior to [111In]−DOTATOC in this respect. The results indicate an improved biological behavior which is likely due to the fact that an additional spacer group separates the chelate from the pharmacophoric part of the somatostatin analogue.

    †

     Institute of Nuclear Medicine.

    ⊥

     K.-P.E. and M.I.M.P contributed equally to these studies.

    ‡

     Departamento de Bioquímica e CNC, Universidade de Coimbra.

    §

     Faculdade de Medicina, Serviço de Biofísica, Universidade de Coimbra.

    ‖

     University of Berne.

    *

     To whom correspondence should be addressed:  Tel:  ++41 61 265 46 99; Fax:  ++41 61 265 55 59, E-mail:  hmaecke@ uhbs.ch.

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