TY - JOUR
T1 - Novel fluorescent Schiff bases as Al3+ sensors with high selectivity and sensitivity, and their bioimaging applications
AU - Berrones-Reyes, Jessica
AU - Muñoz-Flores, Blanca M.
AU - Gómez-Treviño, Alberto
AU - Treto-Suárez, Manuel A.
AU - Páez-Hernández, Dayan
AU - Schott, Eduardo
AU - Zarate, Ximena
AU - Jiménez-Pérez, Víctor M.
N1 - Funding Information:
Financial support and scholarships to J. C. Berrones-Reyes from the Consejo Nacional de Ciencia y Tecnología (CONACyT, México. Grant 240011 ) are acknowledged. FONDECYT 1180565, FONDECYT 1180017, FONDECYT 1161416. Manuel A. Treto-Suárez thank to Ph.D. Program in Molecular Physical Chemistry from Universidad Andrés Bello and subsidy of the DAD-UNAB. The authors thank the Laboratory of Immunology and Virology of FCB-UANL for the bioimaging cells. Millennium Science Initiative of the Ministry of Economy , Development and Tourism-Chile grant Nuclei on Catalytic Processes towards Sustainable Chemistry (CSC).
PY - 2019/5/15
Y1 - 2019/5/15
N2 - A short set of three new Schiff base chemosensors with high selectivity and sensitivity towards Al3+ over other metal cations in aqueous solution were developed and fully characterized. Compounds (E)-1-((L-glutamine-imino)methyl)naphthalen-2-ol (A), (E)-1-((glucosamine-imino)methyl)naphthalen-2-ol (B), and (E)-3-hydroxy-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzoic acid (C) exhibited a significant fluorescence enhancement in the presence of Al3+ over other competitive metal ions with a low detection limit of 0.103, 0.317 and 0.091 μM respectively, much lower than the WHO acceptable limit (0.05 mg/L or 1.85 μM of Al3+) in drinking water. The Schiff base C, shows high sensitivity in aqueous media (Limit of detection, LOD: 0.091 μM) and with a 38-fold (ϕ = 1.64% for Schiff free base; ϕ = 63.91% for Aluminium complex) fluorescence enhancement in the presence of Al3+. The theoretical research has enabled us to rationalize the behaviours of the three selective-sensors to Al3+ synthesized in this work. Based on the design, the amino acid Schiff bases (A) showed good solubility and compatibility with and without Al3+ and some fluorescent bioimaging (FBI) are reported in human epithelial cells Hs27.
AB - A short set of three new Schiff base chemosensors with high selectivity and sensitivity towards Al3+ over other metal cations in aqueous solution were developed and fully characterized. Compounds (E)-1-((L-glutamine-imino)methyl)naphthalen-2-ol (A), (E)-1-((glucosamine-imino)methyl)naphthalen-2-ol (B), and (E)-3-hydroxy-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzoic acid (C) exhibited a significant fluorescence enhancement in the presence of Al3+ over other competitive metal ions with a low detection limit of 0.103, 0.317 and 0.091 μM respectively, much lower than the WHO acceptable limit (0.05 mg/L or 1.85 μM of Al3+) in drinking water. The Schiff base C, shows high sensitivity in aqueous media (Limit of detection, LOD: 0.091 μM) and with a 38-fold (ϕ = 1.64% for Schiff free base; ϕ = 63.91% for Aluminium complex) fluorescence enhancement in the presence of Al3+. The theoretical research has enabled us to rationalize the behaviours of the three selective-sensors to Al3+ synthesized in this work. Based on the design, the amino acid Schiff bases (A) showed good solubility and compatibility with and without Al3+ and some fluorescent bioimaging (FBI) are reported in human epithelial cells Hs27.
KW - Al
KW - Chemosensor
KW - DFT
KW - Fluorescent bioimaging
KW - Schiff bases
UR - http://www.scopus.com/inward/record.url?scp=85066427535&partnerID=8YFLogxK
U2 - 10.1016/j.matchemphys.2019.05.035
DO - 10.1016/j.matchemphys.2019.05.035
M3 - Article
AN - SCOPUS:85066427535
SN - 0254-0584
VL - 233
SP - 89
EP - 101
JO - Materials Chemistry and Physics
JF - Materials Chemistry and Physics
ER -