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 a Petr KLÁN

Základní údaje

Originální název

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

Autoři

ŠTACKOVÁ, Lenka (203 Česká republika, domácí), Peter ŠTACKO (703 Slovensko, domácí) a Petr KLÁN (203 Česká republika, garant, domácí)

Vydání

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

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 14.612

Kód RIV

RIV/00216224:14310/19:00107544

Organizační jednotka

Přírodovědecká fakulta

DOI

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

UT WoS

000466987900047

Klíčová slova anglicky

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

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 2. 2023 21:02, Mgr. Michaela Hylsová, Ph.D.

Anotace

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.

Návaznosti

EF16_013/0001761, projekt VaV

Název: RECETOX RI

GA18-12477S, projekt VaV

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

Investor: Grantová agentura ČR, Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

LM2015051, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Výzkumná infrastruktura RECETOX

6SA17811, interní kód MU

Název: Visible light-activated photocaged molecules for biological applications (Akronym: VLAMBA)

Investor: Jihomoravský kraj, Visible light-activated photocaged molecules for biological applications, Reintegrační granty

Citovat

ŠTACKOVÁ, Lenka, Peter ŠTACKO a 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, roč. 141, č. 17, s. 7155-7162. ISSN 0002-7863. Dostupné z: 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 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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