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New Cyanine–Oligonucleotide Conjugates: Relationships between Chemical Structures and Properties
Author(s) -
Lartia Rémy,
Asseline Ulysse
Publication year - 2006
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/chem.200500908
Subject(s) - cyanine , chemistry , conjugate , oligonucleotide , deoxyribonucleotide , benzothiazole , linker , fluorescence , quinoline , combinatorial chemistry , stereochemistry , dna , organic chemistry , biochemistry , mathematical analysis , physics , mathematics , quantum mechanics , computer science , operating system
Because the influence of the chemical structure of monomethine cyanine–oligo‐2′‐deoxyribonucleotide (ODN) conjugates on their binding and fluorescence properties has remained largely undetermined, we synthesized and studied a wide range of conjugates with various structural patterns. Different cyanine dyes such as thiocyanine, quinocyanine, and thiazole orange isomers were obtained. In the case of unsymmetrical cyanines, the linker was attached to either the quinoline or the benzothiazole nucleus. The influence of the ODN counterpart was evaluated by linking the cyanines to the 5′‐end or to an internucleotidic phosphate. In the first case, the influence of neighboring nucleic bases was studied, whereas in the second, the stereochemical configuration at the phosphorus atom bearing the cyanine was investigated. We report here on relationships between the structures of the dyes and conjugates and some of their properties, such as the stability and fluorescence changes observed on their hybridization with the target sequence. This study provides useful information towards the design of ODN–cyanine conjugates.