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Monofunctionally trans ‐Diammine Platinum( II )‐Modified Peptide Nucleic Acid Oligomers: A New Generation of Potential Antisense Drugs
Author(s) -
Schmidt Kathrin S.,
Boudvillain Marc,
Schwartz Annie,
van der Marel Gijs A.,
van Boom Jacques H.,
Reedijk Jan,
Lippert Bernhard
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021216)8:24<5566::aid-chem5566>3.0.co;2-#
Subject(s) - peptide nucleic acid , nucleic acid , peptide , chemistry , biochemistry , combinatorial chemistry
A solid‐phase approach is described that provides facile access to monofunctionally trans ‐Pt II ‐modified PNA oligomers of arbitrary sequence for potential use both in antigene and antisense strategies. The approach includes the synthesis of a platinated building block 1 and its subsequent incorporation into three different PNA oligomers 5 – 7 by solid‐phase synthesis. In a model cross‐linking reaction one of the latter is found to recognize sequence‐specifically a target oligonucleotide 8 and to cross‐link to it. The resulting structure is the trans ‐Pt II ‐cross‐linked PNA/DNA duplex 9 as revealed by mass spectrometry in combination with a Maxam‐Gilbert sequencing experiment.