Publication Cover
Redox Report
Communications in Free Radical Research
Volume 5, 2000 - Issue 6
720
Views
21
CrossRef citations to date
0
Altmetric
Reviews

The cardioprotective effect of the iron chelator dexrazoxane (ICRF-187) on anthracycline-mediated cardiotoxicity

&
Pages 317-324 | Published online: 19 Jul 2013

  • Salmon SE. Chemotherapeutic agents: cancer chemotherapy. In: Myers FIL, Jawetz E, Goldfien A. (eds) Review of Medical Pharmacology, 7th edn. Los Altos, CA: Lange, 1980; 490-492.
  • Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol 1999; 57: 727–741.
  • Weiss RB. The anthracyclines: will we ever find a better doxorubicin? Semin Oncol 1992; 19: 670–686.
  • Don RT. Cytoprotective agents for anthracyclines. Semin Oncol 1996; 23: 23–34.
  • May PM, Williams GK, Williams DR. Speciation studies of adriamycin, quelamycin, and their metal complexes. Inorg Chim Acta 1980; 46: 221–228.
  • Hasinoff BB, Davey B. Adriamycin and its iron(III) and copper(II) complexes. Biochem Pharmacol 1988; 37: 3663–3669.
  • Minotti G, Cairo G, Monti E. Role of iron in anthracycline cardiotoxicity: new tunes for an old song? FASEB J 1999; 13: 199–212.
  • Minotti G, Cacaliere AF, Mordente A et al. Secondary alcohol metabolites mediate iron delocalization in cytosolic fractions of myocardial biopsies exposed to anticancer anthracyclines. J Clin Invest 1995; 95: 1595–1605.
  • Minotti G, Recalcati S, Mordente A et al. The secondary alcohol metabolite of doxorubicin irreversibly inactivates aconitase/iron regulatory protein-1 in cytosolic fractions from human myocardium. FASEB J 1998; 12: 541–552.
  • Olson RD, Mushlin PS. Doxorubicin cardiotoxicity: analysis of prevailing hypotheses. FASEB J 1990; 4: 3076–3086.
  • Davies KJ, Doroshow JH, Hochstein P. Mitochondrial NADH dehydrogenase-catalyzed oxygen radical production by adriamycin, and the relative iminodaunorubicin. FEBS Lett 1983; 153: 227–230.
  • Doroshow JH. Effect of anthracycline antibiotics on oxygen radical formation in rat heart. Cancer Res 1983; 43: 460–472.
  • Gianni L, Myers CE. The role of free radical formation in the cardiotoxicity of anthracycline. In: Muggia FM, Green MD, Speyer JL. (eds). Cancer Treatment and the Heart, Baltimore, MD: Johns Hopkins University Press, 1992; 9–46.
  • Flint DH, Tuminello JF, Emptage MH. The inactivation of Fe-S cluster containing hydro-lyases by superoxide. J Biol Chem 1993; 268: 22369–22376.
  • Konorev EA, Kennedy C, Kalyanaraman B. Cell-permeable superoxide dismutase and glutathione peroxidase mimetics afford superior protection against doxorubicin-induced cardiotoxicity: The role of reactive oxygen and nitrogen intermediates. Arch Biochem Biophys 1999; 368: 421–428.
  • Myers C. The role of iron in doxorubicin-induced cardiomyopathy. Semin Oncol 1998; 25: 10–14.
  • van Vleet JF, Ferrans JV, Weirich WE. Cardiac disease induced by chronic adriamycin administration in dogs and an elevation of vitamin E and selenium as cardioprotectants. Am J Pathol 1980; 99: 13–42.
  • Myers C, Bonow R, Palmieri S et al. A randomized controlled trial assessing the prevention of doxorubicin in cardiomyopathy by N-acetylcysteine. Semin Oncol 1983; 10: 53–55.
  • Hasinoff BB, Davey B. The iron(M)-adriamycin complex inhibits cytochrome c oxidase before its inactivation. Biochem J 1998; 250: 827–834.
  • Gianni L, Zweier JL, Levy A, Myers CE. Characterization of the cycle of iron-mediated electron transfer from adriamycin to molecular oxygen. J Biol Chem 1985; 260: 6820–6826.
  • Weiss G, Loyevsky M, Gordeuk VR. Dexrazoxane (ICRF-187). Gen Pharmacol 1999; 32: 155–158.
  • Hochster HS. Clinical pharmacology of dexrazoxane. Semin Oncol 1998; 25: 37–42.
  • Hasinoff BB. An HPLC and spectrophotometric study of the hydrolysis of ICRF-187 ((+)-1,2-bis(3,5-dioxopiperazinly-1-yl)propane) and its open-ring hydrolysis intermediates. Int J Pharmacol 1994; 107: 67–76.
  • Buss JL, Hasinoff BB. Ferrous ion strongly promotes the ring opening of the hydrolysis intermediates of the antioxidant cardioprotective agent dexrazoxane (ICRF-187). Arch Biochem Biophys 1995; 317: 121–127.
  • Buss JL, Hasinoff BB. The one-ring open hydrolysis product intermediates of the cardioprotective agent ICRF-187 (dexrazoxane) displace iron from iron-anthracycline complexes. Agents Actions 1993; 40: 86–95.
  • Hasinoff BB. The iron(III) and copper(II) complexes of adriamycin promote the hydrolysis of the cardioprotective agent ICRF-187 ((+)-1,2-bis(3,5-dioxopiperazinly-1-yl)propane). Agents Actions 1990; 29: 374–381.
  • Malisza KL, Hasinoff BB. Inhibition of anthracycline semiquinone formation by ICRF-187 (dexrazoxane) in cells. Free Radic Biol Med 1996; 20: 905–914.
  • Hasinoff BB, Kala SV. The removal of metal ions from transferrin, ferritin and ceruloplasmin by the cardioprotective agent ICRF-187 [(+)-1,2-bis(3,5-dioxopiperazinly-1-yl)propane] and its hydrolysis product ADR-925. Agents Actions 1993; 39: 72–81.
  • Kontoghiorghes GJ, Evans RW. Site specificity of iron removal from transferrin by a-ketohydroxypyridone chelators. FEBS Lett 1985; 189: 141–144.
  • Kontoghiorghes GJ. The study of iron mobilisation from transferrin using alpha-ketohydroxy heteroaromatic chelators. Biochim Biophys Acta 1986; 869: 141–146.
  • Ferrans V, Wasserheit C. Strategies for reduction of anthracycline cardiac toxicity. Semin Oncol 1998; 25: 525–537.
  • Herman E, Ferrans V, Sanchez J. Methods of reducing the cardiotoxicity of anthracycline. In: Muggia FM, Green MD, Speyer JL. (eds). Cancer Treatment and the Heart, Baltimore, MD: Johns Hopkins University Press, 1992; 114–169.
  • Imondi A. Preclinical models of cardiac protection and testing for effects of dexrazoxane on doxorubicin antitumor effects. Semin Oncol 1998; 25 (Suppl 10): 22–30.
  • Imondi AR, Tone PD, Mazue G et al. Dose-response relationship of dexrazoxane for prevention of doxorubicin-induced cardiotoxicity in mice, rats, and dogs. Cancer Res 1996; 56: 4200–4204.
  • Swain SM, Whaley FS, Gerber MC et al. Cardioprotection with dexrazoxane for doxorubicin-containing therapy in advanced breast cancer. J Clin Oncol 1997; 15: 1318–1332.
  • Green MD, Speyer JL, Stecy P et al. ICRF-187 (ICRF) prevents doxorubicin (DOX) cardiotoxicity (CTOX): results of a randomized clinical trial. Proc Am Soc Clin Oncol 1987; 6: 28.
  • Wexler LH, Andrich MP, Venzon D et al. Randomized trial of the cardioprotective agent ICRF-187 in pediatric sarcoma patients treated with doxorubicin. J Clin Oncol 1996; 14: 362–372.
  • Wexler LH. Ameliorating anthracycline cardiotoxicity in children with cancer: clinical trials with dexrazoxane. Semin Oncol 1998; 25: 86–92.
  • Bu'Lock FA, Gavriel H, Oalchill AN et al. Cardioprotection by ICRF-187 against high dose anthracycline toxicity in children with malignant disease. Br Heart J 1993; 70: 185–188.
  • Rubio ME, Wiegman A, Naeff MSJ et al. ICRF-187 (Cardioxane) protection against doxorubicin induced cardiomyopathy in paediatric osteosarcoma patients. Proc Am Soc Clin Oncol 1995; 14: 1403a.
  • Richardson DR, Ponka P. The molecular mechanisms of the metabolism and transport of iron in normal and neoplastic cells. Biochim Biophys Acta 1997; 1331: 1–40.
  • Hentze MW, Kiihn LC. Molecular control of vertebrate iron metabolism: mRNA-based regulatory circuits operated by iron, nitric oxide, and oxidative stress. Proc Natl Acad Sci USA 1996; 93: 8175–8182.
  • Eisenstein RS, Blemings ICP. Iron regulatory proteins, iron responsive elements and iron homeostasis. J Nutr 1998; 128: 2295–2298.
  • Vyoral D, Hradilek A, Neuwirt J. Transferrin and iron distribution in subcellular fractions of K562 cells in early stages of transferrin endocytosis. Biochim Biophys Acta 1992; 1137: 148–154.
  • Richardson DR, Ponka P, Vyoral D. Distribution of iron in reticulocytes after inhibition of heme synthesis with succinylacetone: examination of the intermediates involved in iron metabolism. Blood 1999; 87: 3477–3488.
  • Donovan A, Brownlie A, Zhou Y et al. Positional cloning of zebrafish ferroportin 1 identifies a conserved vertebrate iron exporter. Nature 2000; 403: 776–781.
  • Gunshin H, Mackenzie B, Berger UV et al. Cloning and characterization of a mammalian proton-coupled metal-ion transporter. Nature 1997; 388: 482–488.
  • Kim E, Gin i SN, Pessah IN. Iron(H) is a modulator of ryanodine-sensitive calcium channels of cardiac muscle sarcoplasmic reticulum. Toxicol Appl Pharmacol 1995; 130: 57–66.
  • Bristow M, Thompson P, Martin R et al. Early anthracycline cardiotoxicity. Am J Med 1978; 65: 823–832.
  • Gianni L, Vigan L, Niggeler M et al. Human ferritin (HLF) as iron source for lipid peroxidation by adriamycin (adr). Proc Am Assoc Cancer Res 1988; 29: 378.
  • Minotti G. Adriamycin-dependent release of iron from microsomal membranes. Arch Biochem Biophys 1989; 268: 398–403.
  • Weiss G, Kastner S, Brock J, Thaler J, Grunewald K. Modulation of transferrin receptor expression by dexrazoxane (ICRF-187) via activation of iron regulatory protein. Biochem Pharmacol 1997; 53: 1419–1424.
  • Constable A, Quick S, Gray NK, Hentze MW. Modulation of the RNA-binding activity of a regulatory protein by iron in vitro: Switching between enzymatic and genetic function. Proc Natl Acad Sci USA 1992; 89: 4554–4558.
  • Darnell G, Richardson DR. The potential of analogues of the pyridoxal isonicotinoyl hydrazone class as effective anti-proliferative agents HE the effect of the ligands on molecular targets involved in proliferation. Blood 1999; 94: 781–792.
  • Doroshow JH. Prevention of doxorubicin-induced killing of MCF-7 human breast cancer cells by oxygen radical scavengers and iron chelating agents. Biochem Biophys Res Commun 1986; 135: 330–335.
  • Hershko C, Link G, Tzahor M et al. Anthracycline toxicity is potentiated by iron and inhibited by deferoxamine. Studies in rat heart cells in culture. J Lab Clin Med 1993; 122: 245–251.
  • Richardson DR, Tran EH, Ponka P. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective anti-proliferative agents. Blood 1995; 86: 4295–4306.
  • Richardson DR, Milnes K. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents II. The mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone. Blood 1997; 89: 3025–3038.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.