Fluorescent pH Indicators for Neutral to Near-Alkaline
Conditions Based on 9-Iminopyronin Derivatives

J 2019

Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives

HORVÁTH, Peter, Peter ŠEBEJ, David KOVÁŘ, Jiří DAMBORSKÝ, Zbyněk PROKOP et. al.

Basic information

Original name

Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives

Authors

HORVÁTH, Peter (703 Slovakia, belonging to the institution), Peter ŠEBEJ (703 Slovakia, belonging to the institution), David KOVÁŘ (203 Czech Republic, belonging to the institution), Jiří DAMBORSKÝ (203 Czech Republic, belonging to the institution), Zbyněk PROKOP (203 Czech Republic, belonging to the institution) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

ACS Omega, WASHINGTON, American Chemical Society, 2019, 2470-1343

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: 2.870

RIV identification code

RIV/00216224:14310/19:00107543

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acsomega.9b00362

UT WoS

000462921900103

Keywords in English

HALOALKANE DEHALOGENASES; PROBE; FLUOROPHORES; ANALOGS; DYES; QUANTITATION; CELL

Abstract

V originále

Monitoring enzymatic activities at pH ranges compatible with their physiological optimum using fluorescent assays is important for high-throughput screening and engineering of novel biocatalysts as well as applications in biosensing and diagnostics. However, the number of fluorescent dyes exhibiting necessary optical properties at alkaline pHs is limited. Here, we report the design, synthesis, and biochemical application of fluorescent 9-iminopyronin derivatives possessing unique and distinct emission properties to provide optimal sensitivity at neutral to near-alkaline conditions. They exist in two acid-base forms, allowing for a dual-emission ratiometric sensing with a linear response of pH between 6.0 and 8.5 and detection sensitivity of a 0.06 pH unit. Selected fluorophores were used as the sensors for monitoring the enzymatic hydrolytic activity of a model enzyme haloalkane dehalogenase.

Links

EF16_013/0001761, research and development project

Name: RECETOX RI

GA16-07965S, research and development project

Name: Řízená evoluce dynamických elementů v enzymech s využitím mikrofluidních čipů

Investor: Czech Science Foundation

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

Citovat

HORVÁTH, Peter, Peter ŠEBEJ, David KOVÁŘ, Jiří DAMBORSKÝ, Zbyněk PROKOP and Petr KLÁN. Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives. ACS Omega. WASHINGTON: American Chemical Society, 2019, vol. 4, No 3, p. 5479-5485. ISSN 2470-1343. Available from: https://dx.doi.org/10.1021/acsomega.9b00362.

@article{1548608,
   author = {Horváth, Peter and Šebej, Peter and Kovář, David and Damborský, Jiří and Prokop, Zbyněk and Klán, Petr},
   article_location = {WASHINGTON},
   article_number = {3},
   doi = {http://dx.doi.org/10.1021/acsomega.9b00362},
   keywords = {HALOALKANE DEHALOGENASES; PROBE; FLUOROPHORES; ANALOGS; DYES; QUANTITATION; CELL},
   language = {eng},
   issn = {2470-1343},
   journal = {ACS Omega},
   title = {Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives},
   url = {https://pubs.acs.org/doi/10.1021/acsomega.9b00362},
   volume = {4},
   year = {2019}
}

TY  - JOUR
ID  - 1548608
AU  - Horváth, Peter - Šebej, Peter - Kovář, David - Damborský, Jiří - Prokop, Zbyněk - Klán, Petr
PY  - 2019
TI  - Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives
JF  - ACS Omega
VL  - 4
IS  - 3
SP  - 5479-5485
EP  - 5479-5485
PB  - American Chemical Society
SN  - 24701343
KW  - HALOALKANE DEHALOGENASES
KW  - PROBE
KW  - FLUOROPHORES
KW  - ANALOGS
KW  - DYES
KW  - QUANTITATION
KW  - CELL
UR  - https://pubs.acs.org/doi/10.1021/acsomega.9b00362
L2  - https://pubs.acs.org/doi/10.1021/acsomega.9b00362
N2  - Monitoring enzymatic activities at pH ranges compatible with their physiological optimum using fluorescent assays is important for high-throughput screening and engineering of novel biocatalysts as well as applications in biosensing and diagnostics. However, the number of fluorescent dyes exhibiting necessary optical properties at alkaline pHs is limited. Here, we report the design, synthesis, and biochemical application of fluorescent 9-iminopyronin derivatives possessing unique and distinct emission properties to provide optimal sensitivity at neutral to near-alkaline conditions. They exist in two acid-base forms, allowing for a dual-emission ratiometric sensing with a linear response of pH between 6.0 and 8.5 and detection sensitivity of a 0.06 pH unit. Selected fluorophores were used as the sensors for monitoring the enzymatic hydrolytic activity of a model enzyme haloalkane dehalogenase.
ER  -

HORVÁTH, Peter, Peter ŠEBEJ, David KOVÁŘ, Jiří DAMBORSKÝ, Zbyněk PROKOP and Petr KLÁN. Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives. \textit{ACS Omega}. WASHINGTON: American Chemical Society, 2019, vol.~4, No~3, p.~5479-5485. ISSN~2470-1343. Available from: https://dx.doi.org/10.1021/acsomega.9b00362.

Detailed Information on Publication Record