Fluorescent Cu2+ sensor based on phenanthroline-BODIPY conjugate: A mechanistic study

被引:19
作者
Gorai, Sudip [1 ,2 ]
Ghosh, Ayan [3 ]
Chakraborty, Saikat [1 ]
Retailleau, Pascal [4 ]
Ghanty, Tapan K. [2 ,5 ]
Patro, Birija Sankar [1 ,2 ]
Mula, Soumyaditya [1 ,2 ]
机构
[1] Bhabha Atom Res Ctr, Bioorgan Div, Mumbai 400085, India
[2] Homi Bhabha Natl Inst, Anushakti Nagar, Mumbai 400094, India
[3] Bhabha Atom Res Ctr, Laser & Plasma Technol Div, Mumbai 400085, India
[4] Univ Paris Saclay, Inst Chim Subst Nat, UPR 2301, CNRS, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
[5] Bhabha Atom Res Ctr, Biosci Grp, Mumbai 400085, India
关键词
BODIPY; X-ray crystallography; Fluorescence; Cu 2+sensor; DFT study; INTERMOLECULAR INTERACTIONS; OXIDATIVE STRESS; COPPER; DYES; CHEMOSENSOR; CHEMISTRY; METALS; DESIGN;
D O I
10.1016/j.dyepig.2022.110343
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Development of a specific Cu2+ sensor for the detection of labile Cu2+ ions in vivo in the presence of labile pools of other biologically important metal ions is a real challenge due to similar binding affinity of these metal ions with the ligands containing N and O donor atoms. Here, we designed and synthesized a mixed N- and O-donor atoms containing BODIPY-phenanthroline conjugate where two BODIPY dyes are linked at 2 and 9 position of 1,10-phenanthroline moiety through amide linkage. NMR and X-ray crystallography studies were done to characterize the dye structure. Phenanthroline is a known binder of different metal ions without much selectivity, but the new ligand shows highly selective detection of Cu2+ ions via fluorescent turn off mechanism without any interference with other biologically important metal ions. The sensing mechanism was investigated by detailed photochemical, electrochemical, NMR, FTIR, MALDI-TOF and DFT studies. The BODIPYphenanthroline conjugate forms 1:1 complex with the Cu2+ ion which is confirmed by NMR, MS and DFT studies. Importantly, both dynamic and static quenching processes are responsible for the fluorescence attenuation of the BODIPY-phenanthroline conjugate in the presence of Cu2+ ions. The new ligand is cell-permeable and non-toxic to the cells under tested concentrations. Finally, its potential application to monitor cellular accumulation of Cu2+ ions and detection of Cu2+ in serum samples are also investigated and discussed.
引用
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页数:12
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