TY - JOUR
T1 - Selective determination of glutathione using a highly emissive fluorescent probe based on a pyrrolidine-fused chlorin
AU - Moscoso, Francisco G.
AU - Queirós, Carla
AU - González, Paula
AU - Lopes-Costa, Tânia
AU - Silva, Ana M. G.
AU - Pedrosa, Jose M.
N1 - Publisher Copyright:
© 2023 by the authors.
PY - 2023/1
Y1 - 2023/1
N2 - We report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP) through a 1,3-dipolar cycloaddition approach. First, we describe the coordination of TCPC with Hg(II) ions and the corresponding spectral changes, mainly characterized by a strong quenching of the chlorin emission band. Then, the TCPC-Hg2+ complex exhibits a significant fluorescence turn-on in the presence of low concentrations of the target analyte GSH. The efficacy of the sensing molecule was tested by using different TCPC:Hg2+ concentration ratios (1:2, 1:5 and 1:10) that gave rise to sigmoidal response curves in all cases with modulating detection limits, being the lowest 40 nM. The experiments were carried out under physiological conditions and the selectivity of the system was demonstrated against a number of potential interferents, including cysteine. Furthermore, the TCPC macrocycle did not showed a significant fluorescent quenching in the presence of other metal ions.
AB - We report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP) through a 1,3-dipolar cycloaddition approach. First, we describe the coordination of TCPC with Hg(II) ions and the corresponding spectral changes, mainly characterized by a strong quenching of the chlorin emission band. Then, the TCPC-Hg2+ complex exhibits a significant fluorescence turn-on in the presence of low concentrations of the target analyte GSH. The efficacy of the sensing molecule was tested by using different TCPC:Hg2+ concentration ratios (1:2, 1:5 and 1:10) that gave rise to sigmoidal response curves in all cases with modulating detection limits, being the lowest 40 nM. The experiments were carried out under physiological conditions and the selectivity of the system was demonstrated against a number of potential interferents, including cysteine. Furthermore, the TCPC macrocycle did not showed a significant fluorescent quenching in the presence of other metal ions.
KW - Carboxylated pyrrolidine-fused chlorin
KW - Fluorescence
KW - Glutathione detection
UR - http://www.scopus.com/inward/record.url?scp=85146778000&partnerID=8YFLogxK
U2 - 10.3390/molecules28020568
DO - 10.3390/molecules28020568
M3 - Article
C2 - 36677627
AN - SCOPUS:85146778000
SN - 1420-3049
VL - 28
SP - 1
EP - 12
JO - Molecules
JF - Molecules
IS - 2
M1 - 568
ER -