Table of Contents
Metal-Based Drugs
Volume 5 (1998), Issue 1, Pages 1-9

The Synthesis and Antitumor Activity of the Sodium Salt and Copper (II) Complex of N-[(Trimethylamineboryl)-Carbonyl]-L-Phenylalanine Methyl Ester

1Division of Medicinal Chemistry & Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill 27599-7360, NC, USA
2Boron Biologicals, Inc., 620 Hutton St., Raleigh 27606, NC, USA

Received 9 October 1997; Accepted 24 October 1997

Copyright © 1998 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Sodium N-[(trimethylamineboryl)-carbonyl]-L-phenylalanine 2 and {N-[(trimethylamineboryl)-carbonyl]-L-phenylalanyl- carbxylato}-bis-{N-[(trimethylaminebryl)-carbonyl]-L-phenylalanine} dicopper (II) 3 were successfully synthesized. The agents blocked L1210 leukemic cell DNA and RNA syntheses by inhibiting multiple enzyme activities for nucleic acid synthesis, e.g. PRPP amido transferase, IMP dehydrogenase, DNA polymerase α, thymidine kinase, and TMP kinase. The copper (II) complex 3 demonstrated improved ability to inhibit L1210 partially purified DNA topoisomerase II compared to the parent compound while the sodium salt was inactive at 100 μM.