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Fluorescent Copper(II) Complexes of Asymmetric Bis(Thiosemicarbazone)s: Electrochemistry, Cellular Uptake and Antiproliferative Activity
Author(s) -
Kirtani Deepti U.,
Ghatpande Niraj S.,
Suryavanshi Komal R.,
Kulkarni Prasad P.,
Kumbhar Anupa A.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202101663
Subject(s) - chemistry , semicarbazone , cyclic voltammetry , cytotoxicity , hydrazine (antidepressant) , methylene , nuclear chemistry , electrochemistry , medicinal chemistry , quenching (fluorescence) , fluorescence , stereochemistry , in vitro , biochemistry , physics , electrode , quantum mechanics
Two new Cu(II) complexes, of the type CuL1 and CuL2 , of asymmetric bis(thiosemicarbazone) ligands were synthesized where L1 =(E)‐2‐((E)‐3‐(2‐((E)‐2‐(naphthalen‐1‐yl methylene) hydrazine carbonothioyl) hydrazono) butan‐2‐ylidene) hydrazine carbothioamide and L2 =(E)‐N‐methyl‐2‐(3‐oxobutan‐2‐ylidene) hydrazine carbothioamide and characterized by elemental analysis, HRMS, IR, EPR and cyclic voltammetry. The complexes undergo reversible one‐electron reduction at E 1/2 =∼−0.52 V vs Ag/AgCl. Interaction of CuL1 and CuL2 with human serum albumin monitored by fluorescence spectroscopy revealed static quenching with binding constants of the order of 10 5 M −1 . Their cellular uptake and cytotoxicity were studied on MCF‐7 and NIH‐3T3 cells. The results indicate that CuL1 is more cytotoxic owing to its cellular permeability.