Campus Access Only

All rights reserved. This publication is intended for use solely by faculty, students, and staff of University of the Pacific. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, now known or later developed, including but not limited to photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or the publisher.

Analysis of dirhenium carboxylate : purine dinucleotide adducts

Author

Tiffany Anne Payne, University of the Pacific

Date of Award

2006

Document Type

Thesis - Pacific Access Restricted

Degree Name

Master of Science (M.S.)

Department

Chemistry

First Advisor

Elizabeth F. Day

First Committee Member

Patrick R. Jones

Second Committee Member

James Blankenship

Third Committee Member

Elfie Kraka

Abstract

The discovery of cisplatin, cis-[pt(NH₃)₂Cl₂], as an anticancer agent in 1969 by Rosenbert and his colleagues sparked interest in the area of metal complexes as chemotherapeutic agents. Anticancer dimetal complexes such as Re₂(O₂CCH₂CH₃)₂Br₄·2H₂O are proposed to prevent replication of cancel cells by coordinating to the purine nucleobases in DNA. To investigate the interaction between dimetal compounds and DNA, dirhenium complexes coordinated to purine dinucleotides were isolated and analyzed. LC/MS, HPLC, ¹H NMR, and UV-Visible spectroscopy were used to characterized complexes of Re₂(O₂CR)₂X₄·2H₂O (R = CH₃, CH₂CH₃; X= Cl, Br) with the purine dinucleotides dApG and dGpG. HPLC, UV-Vis, and ¹H NMR are used to investigate the aquation of Re₂(O₂C₂H₃)^{2Cl₄μ2H₂O which may contribute to its biological activity.}

Upon reaction of Re₂₂C₂H₃)^{2Cl₄μ2H₂O with dApG or dGpG, the intact dirhenium:dinucleotide complex is observed by LC/MS after two days. In both of these reactions, dirhenium:GMP complexes are also observes.}

¹H NMR studies show the appearance of new resonances in the aromatic region that cannot be attributed to starting material or hydrolyzed DNA fragments. These resonances are proposed to result from the formation of dirhenium:dinucleotide complexes. Additionally, MS spectra support the conclusion that a complex between the dinuclear rhenium complex and the purine dinucleotides of dApG and dGpG is formed after two days. A dirhenium:nucleotide product is also formed as a result of the dinucleotide hydrolysis.

Pages

122

Recommended Citation

Payne, Tiffany Anne. (2006). Analysis of dirhenium carboxylate : purine dinucleotide adducts. University of the Pacific, Thesis - Pacific Access Restricted. https://scholarlycommons.pacific.edu/uop_etds/629