Structural Modifications of Nile Red Carbon Monoxide
Fluorescent Probe: Sensing Mechanism and Applications

J 2020

Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications

MADEA, Dominik, Marek MARTÍNEK, Lucie MUCHOVA, Jiri VANA, Libor VITEK et. al.

Basic information

Original name

Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications

Authors

MADEA, Dominik (203 Czech Republic, belonging to the institution), Marek MARTÍNEK (203 Czech Republic, belonging to the institution), Lucie MUCHOVA (203 Czech Republic), Jiri VANA (203 Czech Republic), Libor VITEK (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, Washington, D.C. American Chemical Society, 2020, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.354

RIV identification code

RIV/00216224:14310/20:00114239

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.9b03217

UT WoS

000518875700055

Keywords in English

TURN-ON PROBE; LIVING CELLS; SENSITIVE DETECTION; SELECTIVE DETECTION; FLUOROGENIC PROBE; NITRIC-OXIDE; DUAL PROBE; CO; COMPLEXES; DYES

Abstract

V originále

Carbon monoxide (CO) is a cell-signaling molecule (gasotransmitter) produced endogenously by oxidative catabolism of heme, and the understanding of its spatial and temporal sensing at the cellular level is still an open challenge. Synthesis, optical properties, and study of the sensing mechanism of Nile red Pd-based CO chemosensors, structurally modified by core and bridge substituents, in methanol and aqueous solutions are reported in this work. The sensing fluorescence "off-on" response of palladacycle-based sensors possessing low-background fluorescence arises from their reaction with CO to release the corresponding highly fluorescent Nile red derivatives in the final step. Our mechanistic study showed that electron-withdrawing and electron-donating core substituents affect the rate-determining step of the reaction. More importantly, the substituents were found to have a substantial effect on the Nile red sensor fluorescence quantum yields, hereby defining the sensing detection limit. The highest overall fluorescence and sensing rate enhancements were found for a 2-hydroxy palladacycle derivative, which was used in subsequent biological studies on mouse hepatoma cells as it easily crosses the cell membrane and qualitatively traces the localization of CO within the intracellular compartment with the linear quantitative response to increasing CO concentrations.

Links

GA18-12477S, research and development project

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

Investor: Czech Science Foundation

Citovat

MADEA, Dominik, Marek MARTÍNEK, Lucie MUCHOVA, Jiri VANA, Libor VITEK and Petr KLÁN. Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications. Journal of Organic Chemistry. Washington, D.C.: American Chemical Society, 2020, vol. 85, No 5, p. 3473-3489. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.9b03217.

@article{1671637,
   author = {Madea, Dominik and Martínek, Marek and Muchova, Lucie and Vana, Jiri and Vitek, Libor and Klán, Petr},
   article_location = {Washington, D.C.},
   article_number = {5},
   doi = {http://dx.doi.org/10.1021/acs.joc.9b03217},
   keywords = {TURN-ON PROBE; LIVING CELLS; SENSITIVE DETECTION; SELECTIVE DETECTION; FLUOROGENIC PROBE; NITRIC-OXIDE; DUAL PROBE; CO; COMPLEXES; DYES},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications},
   url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b03217},
   volume = {85},
   year = {2020}
}

TY  - JOUR
ID  - 1671637
AU  - Madea, Dominik - Martínek, Marek - Muchova, Lucie - Vana, Jiri - Vitek, Libor - Klán, Petr
PY  - 2020
TI  - Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications
JF  - Journal of Organic Chemistry
VL  - 85
IS  - 5
SP  - 3473-3489
EP  - 3473-3489
PB  - American Chemical Society
SN  - 00223263
KW  - TURN-ON PROBE
KW  - LIVING CELLS
KW  - SENSITIVE DETECTION
KW  - SELECTIVE DETECTION
KW  - FLUOROGENIC PROBE
KW  - NITRIC-OXIDE
KW  - DUAL PROBE
KW  - CO
KW  - COMPLEXES
KW  - DYES
UR  - https://pubs.acs.org/doi/10.1021/acs.joc.9b03217
L2  - https://pubs.acs.org/doi/10.1021/acs.joc.9b03217
N2  - Carbon monoxide (CO) is a cell-signaling molecule (gasotransmitter) produced endogenously by oxidative catabolism of heme, and the understanding of its spatial and temporal sensing at the cellular level is still an open challenge. Synthesis, optical properties, and study of the sensing mechanism of Nile red Pd-based CO chemosensors, structurally modified by core and bridge substituents, in methanol and aqueous solutions are reported in this work. The sensing fluorescence "off-on" response of palladacycle-based sensors possessing low-background fluorescence arises from their reaction with CO to release the corresponding highly fluorescent Nile red derivatives in the final step. Our mechanistic study showed that electron-withdrawing and electron-donating core substituents affect the rate-determining step of the reaction. More importantly, the substituents were found to have a substantial effect on the Nile red sensor fluorescence quantum yields, hereby defining the sensing detection limit. The highest overall fluorescence and sensing rate enhancements were found for a 2-hydroxy palladacycle derivative, which was used in subsequent biological studies on mouse hepatoma cells as it easily crosses the cell membrane and qualitatively traces the localization of CO within the intracellular compartment with the linear quantitative response to increasing CO concentrations.
ER  -

MADEA, Dominik, Marek MARTÍNEK, Lucie MUCHOVA, Jiri VANA, Libor VITEK and Petr KLÁN. Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications. \textit{Journal of Organic Chemistry}. Washington, D.C.: American Chemical Society, 2020, vol.~85, No~5, p.~3473-3489. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.9b03217.

Detailed Information on Publication Record