Coumarine-imino-C2-glucosyl conjugate as receptor for Cu(2+) in blood serum milieu, on silica gel sheet and in Hep G2 cells and the characterization of the species of recognition.
A coumarine-imino-C2-glucosyl conjugate (L) was synthesized and characterized. The conjugate L is found to recognize Cu(2+) in aqueous HEPES buffer by exhibiting a 95% fluorescence quenching in pH range 7-10 even in the presence of several biologically and ecologically relevant metal ions. Fluorescence on-off behavior has been clearly demonstrated on the basis of the binding variability of Cu(2+) to L. The binding has been elicited through the changes observed in fluorescence, absorption, ESI-MS and (1)H NMR titrations. All the other thirteen metal ions studied did not show any change in the fluorescence emission. These ions do not interfere with the recognition of Cu(2+) by L. The structural features of [CuL]2 complex in both the isomeric forms were established by DFT computational calculations. The utility of L has been demonstrated by showing its sensitivity toward Cu(2+) on a thin layer of silica gel. The L gives sensitive fluorescence signals for Cu(2+) even in blood serum and exhibits appropriate fluorescence responses in living cells.
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Sivaiah
S
Areti
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Jayshree K
JK
Khedkar
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Sateesh
S
Bandaru
Department of Chemical Engineering, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Rohit
R
Teotia
Department of Chemical Engineering, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Jayesh
J
Bellare
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India. Electronic address: cprao@iitb.ac.in.
Chebrolu Pulla
CP
Rao
D002413:Cations, Divalent / Q000032:analysis / Q000097:blood; D003300:Copper / Q000032:analysis* / Q000097:blood*; D003374:Coumarins / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D057230:Limit of Detection; D008958:Models, Molecular; D058428:Silica Gel / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D002413:Cations, Divalent; D003374:Coumarins; D058428:Silica Gel; D003300:Copper
Blood serum milieu; Coumarine–imino–C2-glucosyl conjugate; Selective recognition of Cu(2+); Silica gel solid support; Switch-off fluorescence