Synthesis, Structure And In Vitro Anticancer Studies Of Dinuclear Silver(I)-N-Heterocyclic Carbene Complexes Derived From Xylyl Linked Bis-Benzimidazolium Salts
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Date
2014-01
Authors
Iqbal, Muhammad Adnan
Journal Title
Journal ISSN
Volume Title
Publisher
Universiti Sains Malaysia
Abstract
The current study was aimed to synthesize three series of bisbenzimidazolium
salts (12-44) as stable N-heterocyclic carbene (NHC) precursors
and their complexation with silver(I) ions in order to obtain dinuclear silver(I)-NHC
complexes (45-77). Each series of salts was derived either from para-, meta-, or
ortho-xylene linked systems having ethyl-decyl, benzyl and i-propyl substituents at
number 3-position of benzimidazolium ring. The salts and complexes were
characterized by spectroscopy (FT-IR, 1H and 13C NMR), elemental analysis (CHN)
and single crystal X-ray diffraction techniques. All the complexes were prepared by
in situ reaction of Ag2O with the corresponding bis-benzimidazolium salts and were
tested against human colon cancer cells. Selected salts (12-14, 18-20, 21) and
respective complexes (45-47, 29-31, 54) were further tested against acute
promyelocytic leukaemia and immortalized myelogenous leukaemia cells. The
compounds showed potential anticancer activity against all the tested cancer cell
lines. Moreover, complexes exhibited higher cytotoxicity compared to respective
salts. The anticancer potential of compounds increased with the increase in chain
length at position 3-nitrogen. Furthermore, considering the triangular relationship
among cancer, inflammation and oxidation, selected compounds were further tested
for possible anti-oxidant and anti-inflammatory activities. The tested compounds did
not show anti-oxidant behaviour however, proved to have anti-inflammatory activity
comparable to the standards used.
Description
Keywords
Dinuclear Silver(I)-N-Heterocyclic Carbene , Bis-Benzimidazolium Salts