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@article{1548609, author = {Štacková, Lenka and Štacko, Peter and Klán, Petr}, article_location = {Washington}, article_number = {17}, doi = {http://dx.doi.org/10.1021/jacs.9b02537}, keywords = {IN-VIVO; SELECTIVE DETECTION; FLUORESCENT-PROBE; DYES; CELLS; REACTIVITY; FLUOROPHORES; GLUTATHIONE; NAVIGATION; DESIGN}, language = {eng}, issn = {0002-7863}, journal = {Journal of the American Chemical Society}, title = {Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts}, url = {https://pubs.acs.org/doi/10.1021/jacs.9b02537}, volume = {141}, year = {2019} }
TY - JOUR ID - 1548609 AU - Štacková, Lenka - Štacko, Peter - Klán, Petr PY - 2019 TI - Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts JF - Journal of the American Chemical Society VL - 141 IS - 17 SP - 7155-7162 EP - 7155-7162 PB - American Chemical Society SN - 00027863 KW - IN-VIVO KW - SELECTIVE DETECTION KW - FLUORESCENT-PROBE KW - DYES KW - CELLS KW - REACTIVITY KW - FLUOROPHORES KW - GLUTATHIONE KW - NAVIGATION KW - DESIGN UR - https://pubs.acs.org/doi/10.1021/jacs.9b02537 L2 - https://pubs.acs.org/doi/10.1021/jacs.9b02537 N2 - Cyanine dyes play an indispensable and central role in modern fluorescence-based biological techniques. Despite their importance and widespread use, the current synthesis methods of heptamethine chain modification are restricted to coupling reactions and nucleophilic substitution at the meso position in the chain. Herein, we report the direct transformation of Zincke salts to cyanine dyes under mild conditions, accompanied by the incorporation of a substituted pyridine residue into the heptamethine scaffold. This work represents the first general approach that allows the introduction of diverse substituents and different substitution patterns at the C3'-C5' positions of the chain. High yields, functional tolerance, versatility toward the condensation partners, and scalability make this method a powerful tool for accessing a new generation of cyanine derivatives. ER -
ŠTACKOVÁ, Lenka, Peter ŠTACKO a Petr KLÁN. Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts. \textit{Journal of the American Chemical Society}. Washington: American Chemical Society, 2019, roč.~141, č.~17, s.~7155-7162. ISSN~0002-7863. Dostupné z: https://dx.doi.org/10.1021/jacs.9b02537.
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