Postsynthetic derivatization of fluorophores with alpha-sulfo-beta-alanine dipeptide linker. Application to the preparation of water-soluble cyanine and rhodamine dyes.
A straightforward method to enhance water solubility of fluorescent organic dyes (cyanines and rhodamines) by a postsynthetic chemical derivatization of their carboxylic acid functionality with an original disulfonated heterobifunctional linker is described. Significant water solubility enhancement is achieved without compromising either the photophysical properties (especially large molar extinction coefficients and high quantum yields) or bioconjugation efficiency of the parent non-water-soluble fluorophores. The results both demonstrate the strong potential of these new compounds as fluorescent labels for a broad range of biotechnology and biomedical applications and illustrate the utility of such an easy-to-handle water-solubizing group.
Romieu
Anthony
A
Equipe de Chimie Bio-Organique, Université de Rouen, INSA de Rouen, CNRS UMR 6014, COBRA, IRCOF, 1, rue Lucien Tesnière, 76131 Mont-Saint-Aignan Cedex, France. anthony.romieu@univ-rouen.fr
Brossard
Dominique
D
Hamon
Maxime
M
Outaabout
Hakim
H
Portal
Christophe
C
Renard
Pierre-Yves
PY
D000042:Absorption; D002232:Carbocyanines / Q000138:chemical synthesis / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D055095:Optics and Photonics; D012235:Rhodamines / Q000138:chemical synthesis / Q000737:chemistry*; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water / Q000737:chemistry*; D014966:Xanthenes / Q000138:chemical synthesis / Q000737:chemistry; D015091:beta-Alanine / Q000031:analogs & derivatives / Q000737:chemistry*
C098793:CY5.5 cyanine dye; D002232:Carbocyanines; D004151:Dipeptides; D005456:Fluorescent Dyes; D012235:Rhodamines; D014966:Xanthenes; C026188:rhodamine 6G; D014867:Water; D015091:beta-Alanine; C034657:Texas red