A fast and responsive turn-on fluorescent probe based on a quinone conjugated alkoxy derivative for biothiols and a cellular imaging study

Authors

ULVIYYE NEMETOVAFollow
AYŞE NUR ÖNEMFollow
ALEV ERFollow
SEFA ÇELİKFollow
AYŞEN E. ÖZELFollow
SEVİM AKYÜZFollow
MUSTAFA ÖZYÜREKFollow
SİBEL ŞAHİNLER AYLAFollow

Abstract

Detection of intracellular biothiols (cysteine (CYS), N-acetyl cysteine (NAC) and glutathione (GSH)) with high-selectivity and sensitivity is important to reveal biological functions. In this study, 2-(2-methoxy-4-methylphenoxy)-3-chloro-5,8-dihydroxynaphthalene-1,4-dione (3) (DDN-O) compound was newly synthesized and used as a fluorogenic probe (detector molecule) in the fluorometric method for the rapid, highly selective and sensitive determination of biothiols. The intensity values (λex = 260 nm, λem = 620 nm) of the product were measured by adding biotihols to the reaction medium at varying concentrations and the glutathione equivalent thiol content (GETC) values of each biotiol were calculated. Using the compoud (3), the reference biotiol GSH was detected in the linear concentration range of 10-70 μM and the LOD value was found to be 0.11 μM. Biothiol detection with the structurally simple compoud (3) was performed at the cellular level within 1 min, and this probe has also been successfully used in bioimaging with low citotoxicity. It is evaluated that this probe can be an alternative to existing fluorescence-based biothiol probes, can be used in rapid biothiol detection at the cellular level in biological functions. To evaluate the molecular structure of (3), conformational analysis was performed using the PM3 semi-empirical method. The obtained most stable molecular geometry was then optimized at DFT/wb97xd/6-311++G(d,p) level of theory. Frontier molecular orbitals (HOMO and LUMO) and molecular electrostatic potential (MEP) map analyses were performed for the optimized structure. The molecular docking studies demonstrated the interactions of (3) with HAS (1AO6) and FhGST (2FHE) target proteins.

Author ORCID Identifier

ULVIYYE NEMETOVA: 0000-0003-1038-5074

AYŞE ÖNEM: 0000-0002-6201-6740

ALEV ER: 0000-0002-3190-5342

SEFA ÇELİK: 0000-0001-6216-1297

AYŞEN ÖZEL: 0000-0002-8680-8830

SEVİM AKYÜZ: 0000-0003-3313-6927

MUSTAFA ÖZYÜREK: 0000-0001-5426-9775

SİBEL ŞAHİNLER AYLA: 0000-0002-1332-1968

DOI

10.55730/1300-0527.3702

Keywords

Biothiols, 2, 3-dichloro-5, 8-dihydroxynaphthalene-1, 4-dione, fluorogenic probe, bioimaging, molecular modeling, molecular docking

First Page

830

Last Page

842

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Recommended Citation

NEMETOVA, ULVIYYE; ÖNEM, AYŞE NUR; ER, ALEV; ÇELİK, SEFA; ÖZEL, AYŞEN E.; AKYÜZ, SEVİM; ÖZYÜREK, MUSTAFA; and ŞAHİNLER AYLA, SİBEL (2024) "A fast and responsive turn-on fluorescent probe based on a quinone conjugated alkoxy derivative for biothiols and a cellular imaging study," Turkish Journal of Chemistry: Vol. 48: No. 6, Article 5. https://doi.org/10.55730/1300-0527.3702
Available at: https://journals.tubitak.gov.tr/chem/vol48/iss6/5