Akademik Veri Yönetim Sistemi
TURKISH JOURNAL OF CHEMISTRY, cilt.1, ss.1-31, 2024 (SCI-Expanded, Scopus, TRDizin)
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) 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 probe (3) (DDN-O), 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 probe (3) probe 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.