The mechanisms of cytotoxicity of the antitumour diaziridinylbenzoquinones, AZQ and BZQ, have been investigated. HPLC analysis has been used to study the products as well as the rate of decomposition of acid-assisted ring-opening in aqueous medium as a function of pH. Microconcentrators with a molecular weight cutoff of 30 kDa were utilised to study the covalent binding of both compounds to calf thymus DNA. Radical production of both compounds in K562 cell incubations was followed using ESR and their uptake into K562 cells was monitored using radiolabelled compounds. The results show that these two diaziridinylbenzoquinones, although very similar in structure, have diverse mechanisms of cytotoxicity. The implications of these findings are discussed in the light of antitumor action.

Dedicated to Professor Mieczyslaw Makosza on the occasion his 70th birthday (received 01 Aug 03; accepted 29 Sept 03; published on the web 02 Oct 03) Abstract 2-Amino-2-methyl-3-(4-dihydroxyborylphenyl)propionic acid (3, α-methyl-BPA) and 1-amino-3-(4-dihydroxyborylbenzyl)cyclobutanecarboxylic acid 4, which are (4-dihydroxyborylphenyl)alanine (BPA) analogues containing a quaternary center, have been synthesized from 4-allylbromobenzene. α-Methyl-BPA has also been prepared from D,L-alanine, and the route is suitable for the synthesis of α-alkyl-BPA. Both 3 and 4 exhibit very similar R f values indicating similar lipophilicities. The products have been prepared as potential boron carriers for Boron Neutron Capture Therapy.

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