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Synthesis and peptide coupling of a new DOTA‐based prochelator, forming neutral complexes with yttrium‐90 and indium‐111
Author(s) -
Eisenwiener KlausPeter,
Reubi JeanClaude,
Wenger Sandra,
Mäcke Helmut R.
Publication year - 2001
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.25804401245
Subject(s) - chemistry , dota , octreotide , peptide , chelation , yttrium , somatostatin , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , medicine , oxide
As a result of positive effects of the chelators DOTA and DOTAGA, when coupled to Tyr 3 ‐octreotide, we designed a new potential chelator, DOTAtaGA, which combines these effects. DOTAtaGA has a spacer between the pharmacophoric part of the peptide and the chelator and forms neutral complexes with Y iii and In III , as in the case of Y‐DOTA‐Tyr 3 ‐octreotide. The corresponding prochelator DOTAtaGA(tBu) 3 (1, 4, 7, 10‐tetraazacyclododecane‐1‐(1‐carboxy‐3‐carbo‐ ter tbutoxypropyl)‐4, 10 (carbo tert butoxymethyl)‐7‐acetamide) was synthesized in 3 steps with an overall yield of 16.5%. It was coupled to Tyr 3 ‐octreotide, and the resulting peptide DOTAtaGA‐Tyr 3 ‐octreotide has a ten times higher binding affinity to the somatostatin receptor subtype 2 than DOTA‐TOC.