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In vitro evidence for direct complexation of ADR-529/ICRF-187 [(+)-1,2- bis-(3,5-dioxo-piperazin-1-yl)propane] onto an existing ferric- anthracycline complex

MM Sobol, RG Amiet and MD Green

Department of Medical Oncology and Clinical Haematology, Royal Melbourne Hospital, Australia.

ADR-529 protects against anthracycline cardiotoxicity, possibly by preventing free radical induction. We hypothesize that this occurs by ADR-529 forming a ternary anthracycline-iron-ADR-529 complex. This study used 200-MHz Fourier-transformed NMR to demonstrate the ability of ADR-529 to do this. Peak assignments were by proton-correlated spectroscopy and proton-carbon heteronuclear-correlated spectroscopy. Ga3+ served as a probe for Fe3+, and D2O was the system solvent. Doxorubicin and epirubicin were the studied drugs. Proton spectra of multiple combinations (including pure standards as controls) were obtained. Both Ga3+ plus ADR-529 and Ga3+ plus doxorubicin showed evidence of complexation, as seen by appropriate peak shifts and changes in the associated coupling constants. Ga3+ plus ADR-529 plus epirubicin showed complexation different from that of Ga3+ plus ADR-529 or Ga3+ plus doxorubicin and consistent with the proposed structure. We conclude that ADR-529 would be able to form a ternary complex with an existing anthracycline-Fe3+ complex in an isolated aqueous environment.

Volume 41, Issue 1, pp. 8-17, 01/01/1992
Copyright © 1992 by American Society for Pharmacology and Experimental Therapeutics




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