Gold(III) Complexes as Potential Anticancer Metallotherapeutics Open Access

Ahuja, Neha (2012)

Permanent URL: https://etd.library.emory.edu/concern/etds/00000029z?locale=en
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Abstract

Abstract

Gold(III) Complexes as Potential Anticancer Metallotherapeutics

By Neha Ahuja

Gold(III) complexes are emerging as potential candidates for anticancer metallotherapeutic agents. Gold complexes are proposed to bring about their therapeutic activity in a mechanism different from that of cispaltin.1 The unique properties of gold are being explored by complexing it with the appropriate ligand scaffold that makes the gold complexes target specific.2 This report describes the results for the attempted synthesis and characterization of two Au(III) complexes with the 5-nitro-1,10-phenanthroline and 5-amino-1,10-phenathroline ligands. The substituted phenanthroline ligands render different properties to their respective complexes in terms of their stability and activity in solution. Previously synthesized 2,9-dialkyl substituted, [(sec-butylphenanthroline)AuCl3] when tested in vitro was found to be more cytotoxic that cisplatin towards selected human cancer cell lines, with their IC50 values 2-8 times lower than the values for cisplatin. 3 Substituting functional groups instead of dialkyl groups, on the aromatic backbone lowers the overall hydrocarbon character of the complexes. This would help in enhancing the hydrophilic properties of complexes, which is an essential property required for their in vitro cytotoxicity assays, and make them suitable candidates for in vivo testing for their applications as anticancer agents. The synthesis and characterization of the Au(III) complexes with the substituted phenanthroline ligands is reported. Cu(II) complexes of the ligands have also been prepared to understand the behavior of gold(III) complexes in solution state and elaborate and compare the chemistry of ligands with other metal centers.

Table of Contents

Table of Contents

Section Page

List of Figures

List of Schemes

List of Tables

List of Equations

Introduction 1

Au(III) chemistry 1

Ligands and their significance 3

Reducing agents 4

Cisplatin and its mode of action 4

The proposed mitochondrial pathway 5

Results and Discussion 10

Synthesis and spectroscopic characterization of [(nitrophenanthroline)AuCl3] 10

Synthesis and spectroscopic characterization of [(aminophenanthroline)AuCl3] 16

Stability studies in presence of reducing agents 20

Calculation of logP 26

X-ray Crystallographic studies 27

Alternative synthetic approach 30

Conclusions 40

Experimental 41

References 51

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