3-spiro-cyanin fluorochromes and their use in bioassays

C - Chemistry – Metallurgy – 09 – B

Patent

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Details

C09B 23/00 (2006.01) C07D 471/10 (2006.01) C07D 491/107 (2006.01) C09B 23/02 (2006.01) G01N 33/50 (2006.01) G01N 33/533 (2006.01)

Patent

CA 2422758

The invention relates to sterically shielded, stabilised fluorescent dyes based on symmetrical or asymmetrical 3-spiro cyanins and to their use as labelling molecules in analytical methods. The inventive fluorochromes are characterised in particular in that they exhibit a significantly reduced tendency to aggregate as a result of the introduction of the bulky spiro hydrocarbon substituents and thus enable a high degree of coupling to the target molecule, without any fluorescence quenching by quench effects being observed. The fluorochromes have a high quantum yield and are therefore eminently suitable for use as fluorescent dyes, in particular as a NIR fluorescent dye for the coupling or bonding of biomolecules for use in bioassays. The analytical methods cover all methods, in which biomolecules are detected with the help of fluorescent optical procedures.

La présente invention concerne des agents de coloration par fluorescence stables à encombrement stérique, se basant sur des 3-spirocyanines symétriques ou asymétriques, ainsi que leur utilisation en tant que molécules de marquage dans des procédés analytiques. Les fluorochromes de l'invention se caractérisent notamment en ce qu'ils présentent un tendance à l'agrégation fortement limitée grâce à l'introduction de substituants de spirane volumineux, et permettent ainsi d'obtenir un degré de couplage élevé à la molécule cible sans qu'aucune disparition de fluorescence provoquée par des effets d'extinction de ne soit constatée. Ils ont ainsi un rendement quantique élevé et conviennent particulièrement en tant qu'agents de coloration par fluorescence, notamment en tant qu'agents de coloration par fluorescence NIR, pour le couplage ou la liaison de biomolécules destinées à être utilisées dans des essais biologiques. Les procédés analytiques comprennent tous les procédés dans lesquels des biomolécules sont détectées par optique de fluorescence.

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