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Synthesis and properties of radiolabeled CPTA–oligonucleotides
Author(s) -
Wagner S.,
Eritja R.,
Zuhayra M.,
Oberdorfer F.,
Mohammed A.,
Mier W.,
Haberkorn U.,
Eisenhut M.
Publication year - 2003
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.656
Subject(s) - chemistry , conjugated system , combinatorial chemistry , benzoic acid , oligonucleotide , dna , organic chemistry , biochemistry , polymer
A solid phase technique for the preparation of antisense oligodeoxynucleotides (ODNs) is described featuring 5′‐end conjugated 4‐[(1,4,8,11‐tetraazacyclotet‐radec‐1‐yl)‐methyl]benzoic acid (CPTA). Using Fmoc‐protected CPTA–C6 amidite, CPTA was conjugated to ODNs at the end of an automated DNA synthesis. To illustrate successful conjugations, the CPTA–ODNs were labeled with 99m Tc using the stannous‐chloride reduction method. The resulting 99m Tc complexes showed differences of stability between CPTA‐conjugated and CPTA‐unconjugated as well as 3′‐protected and 3′‐unprotected ODNs. Propane‐1,3‐diol 3′‐modification enhanced efficiently the stability of 99m Tc labeled ODN against exonuclease degradation. Fmoc 3 CPTA‐C6 amidite turned out to be a versatile ligand for radiometal complexation at the 5′‐end. Copyright © 2002 John Wiley & Sons, Ltd.