Synthesis, Characterization, and Anticancer Activity of Gold(III) Complexes Bearing Alkyl-substituted 1,10-phenantroline Ligands

Authors:

ChiHyun Hwang, ChiHyun Hwang

Mentor:

Jack Eichler, Assistant professor of teaching, Univerisity of California, Riverside

In an ongoing effort to develop alternatives to the anti-cancer drug cisplatin, we have previously reported a gold(III) complex possessing 2,9-di-sec-butyl-phenanthroline ligand {[(sec-butylphen)AuCl3]}. This new gold complex was shown to demonstrate enhanced reduced glutathione (GSH) stability as well as in vitro cytotoxicity toward several cell lines. However, it is thought that this complex interacts with blood serum albumin proteins, resulting in limited delivery of the drug to the in-vivo tumor. This hypothesis was confirmed by recent model studies with bovine serum albumin (BSA) protein. Our current goal is to make analogous complexes to [(sec-butylphen)AuCl3] that can limit the binding with BSA, but still demonstrate stability in the presence of GSH and exhibit higher anti-tumor activity. We have successfully synthesized and analyzed two new ligands{[2-sec-butyl-1,10-phenanthroline (mono-sec-butylphen)}, and 2,9-di-sec-butyl-4-methyl-1,10-phenanthroline (methyl-sec-butylphen)], and made gold(III) complexes with both new ligands. We have confirmed the complexes' geometry through 1H NMR and single crystal x-ray diffraction. The new gold(III) complexes have been found to possess similar GSH stability to the original [(sec-butylphen)AuCl3] complex, and based on our observation, both complexes have similar binding to the model BSA. It is also reported that even though the mono-sec-butylphen and methyl-sec-butylphen ligands have comparable in vitro antitumor activity to the original sec-butylphen ligand, the [(monosec-butylphen)AuCl3] and [(methylsec-butylphen)AuCl3] complexes have significantly lower antitumor activity than the original [(sec-butylphen)AuCl3] complex.


Presented by:

ChiHyun Hwang, ChiHyun Hwang

Date:

Saturday, November 23, 2013

Poster:

39

Room:

Poster Session 1 - Villalobos Hall

Presentation Type:

Poster Presentation

Discipline:

Chemistry