Synthesis and biological evaluation of copper(ii) pyrenethiosemicarbazone

Abstract

A fluorescent Cu(ii) pyrenethiosemicarbazone complex exhibits enhanced DNA-cleavage and cytotoxicity on photoexcitation.

Fluorescent Copper(II) Complexes of Asymmetric Bis(Thiosemicarbazone)s: Electrochemistry, Cellular Uptake and Antiproliferative Activity

“…Further, same emission maxima in CuL1 and CuL2 suggests that the emission in these complexes is ligand‐based. This can be attributed to the separation of excited states of copper(II) and the ligand via distortion in the geometry of the complex in the excited state [49,50] . Similar observations were noted by Holland and coworkers on pyrene functionalized bis(thiosemicarbazonato) copper(II) complexes and explained on the basis of single photon emission experiments combined with the density functional theoretical calculations [76] …”

“…This can be attributed to the separation of excited states of copper(II) and the ligand via distortion in the geometry of the complex in the excited state. [49,50] Similar observations were noted by Holland and coworkers on pyrene functionalized bis(thiosemicarbazonato) copper(II) complexes and explained on the basis of single photon emission experiments combined with the density functional theoretical calculations. [76] The stabilization of copper in + 2 oxidation state was confirmed by X-band EPR spectra of CuL1 and CuL2 recorded in DMF at liquid nitrogen temperature.…”

“…The list of asymmetric ligands and their Cu(II) complexes has been expanded recently by Went et al by studying the effect of alkylation on lipophilicity and redox potentials [47] . Earlier, we have demonstrated the cellular uptake of Cu(II) complexes by tagging them with DNA‐binding fluorophores like naphthalene, [48] anthracene [49] and pyrene [50] . Encouraged by the results, we have taken it further to develop fluorescent bis(TSC) Cu(II) complexes [51] .…”

“…[47] Earlier, we have demonstrated the cellular uptake of Cu(II) complexes by tagging them with DNA-binding fluorophores like naphthalene, [48] anthracene [49] and pyrene. [50] Encouraged by the results, we have taken it further to develop fluorescent bis(TSC) Cu(II) complexes. [51] By tagging a fluorophore to bis(TSC) ligands, the localization of these complexes can be followed in cells by using fluorescence microscopy.…”

Thiosemicarbazone Moiety Assist in Interaction of Planar Aromatic Molecules with Amyloid Beta Peptide and Acetylcholinesterase

“…(Scheme ) TSC 1 is reported for its inhibitory activity against mushroom tyrosinase . TSC 2 and TSC 3 were reported for their protein binding, anticancer activity as well as antiviral property . We first carried out drug likeness prediction studies to evaluate hydrophobicity and solubility of these TSC analogues.…”