Approach to a Substituted Heptamethine Cyanine Chain by the
Ring Opening of Zincke Salts

J 2019

Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts

ŠTACKOVÁ, Lenka, Peter ŠTACKO and Petr KLÁN

Basic information

Original name

Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts

Authors

ŠTACKOVÁ, Lenka (203 Czech Republic, belonging to the institution), Peter ŠTACKO (703 Slovakia, belonging to the institution) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of the American Chemical Society, Washington, American Chemical Society, 2019, 0002-7863

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 14.612

RIV identification code

RIV/00216224:14310/19:00107544

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/jacs.9b02537

UT WoS

000466987900047

Keywords in English

IN-VIVO; SELECTIVE DETECTION; FLUORESCENT-PROBE; DYES; CELLS; REACTIVITY; FLUOROPHORES; GLUTATHIONE; NAVIGATION; DESIGN

Abstract

V originále

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.

Links

EF16_013/0001761, research and development project

Name: RECETOX RI

GA18-12477S, research and development project

Name: Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

6SA17811, interní kód MU

Name: Visible light-activated photocaged molecules for biological applications (Acronym: VLAMBA)

Investor: South-Moravian Region, Incoming grants

Citovat

ŠTACKOVÁ, Lenka, Peter ŠTACKO and Petr KLÁN. Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts. 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.

@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.

Detailed Information on Publication Record