Targeting somatostatin receptors: preclinical evaluation of novel 18F-fluoroethyltriazole-Tyr3-octreotate analogs for PET

J Nucl Med. 2011 Sep;52(9):1441-8. doi: 10.2967/jnumed.111.088906. Epub 2011 Aug 18.

Abstract

The incidence and prevalence of gastroenteropancreatic neuroendocrine tumors has been increasing over the past 3 decades. Because of high densities of somatostatin receptors (sstr)--mainly sstr-2--on the cell surface of these tumors, (111)In-diethylenetriaminepentaacetic acid-octreotide scintigraphy has become an important part of clinical management. (18)F-radiolabeled analogs with suitable pharmacokinetics would permit PET with more rapid clinical protocols.

Methods: We compared the affinity in vitro and tissue pharmacokinetics by PET of 5 structurally related (19)F/(18)F-fluoroethyltriazole-Tyr(3)-octreotate (FET-TOCA) analogs: FET-G-polyethylene glycol (PEG)-TOCA, FETE-PEG-TOCA, FET-G-TOCA, FETE-TOCA, and FET-βAG-TOCA to the recently described (18)F-aluminum fluoride NOTA-octreotide ((18)F-AIF-NOTA-OC) and the clinical radiotracer (68)Ga-DOTATATE.

Results: All (19)F-fluoroethyltriazole-Tyr(3)-octreotate compounds retained high agonist binding affinity to sstr-2 in vitro (half-maximal effective concentration, 4-19 nM vs. somatostatin at 5.6 nM). Dynamic PET showed that incorporation of PEG linkers, exemplified by (18)F-FET-G-PEG-TOCA and (18)F-FETE-PEG-TOCA, reduced uptake in high sstr-2-expressing AR42J pancreatic cancer xenografts. (18)F-FET-βAG-TOCA showed the lowest nonspecific uptake in the liver. Tumor uptake increased in the order (68)Ga-DOTATATE < (18)F-AIF-NOTA ≤ (18)F-FET-βAG-TOCA < (18)F-FET-G-TOCA. The uptake of (18)F-FET-βAG-TOCA was specific: a radiolabeled scrambled peptide, (18)F-FET-βAG-[W-c-(CTFTYC)K], did not show tumor uptake; there was lower uptake of (18)F-FET-βAG-TOCA in AR42J xenografts when mice were pretreated with 10 mg of unlabeled octreotide per kilogram; and there was low uptake of (18)F-FET-βAG-TOCA in low sstr-2-expressing HCT116 xenografts.

Conclusion: We have developed novel fluoroethyltriazole-Tyr(3)-octreotate radioligands that combine high specific binding with rapid target localization and rapid pharmacokinetics for high-contrast PET. (18)F-FET-βAG-TOCA and (18)F-FET-G-TOCA are candidates for future clinical evaluation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Female
  • Mice
  • Mice, Inbred BALB C
  • Neoplasm Transplantation
  • Neoplasms, Experimental / diagnostic imaging
  • Octreotide / analogs & derivatives*
  • Octreotide / chemical synthesis
  • Octreotide / pharmacokinetics
  • Organometallic Compounds
  • Polyethylene Glycols / chemistry
  • Positron-Emission Tomography / methods
  • Radiopharmaceuticals* / chemical synthesis
  • Radiopharmaceuticals* / pharmacokinetics
  • Receptors, Somatostatin / metabolism*
  • Structure-Activity Relationship
  • Substrate Specificity
  • Tissue Distribution

Substances

  • Organometallic Compounds
  • Radiopharmaceuticals
  • Receptors, Somatostatin
  • Polyethylene Glycols
  • gallium Ga 68 dotatate
  • Octreotide