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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 and 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, vol.~141, No~17, p.~7155-7162. ISSN~0002-7863. Available from: https://dx.doi.org/10.1021/jacs.9b02537.
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