Abstract
Nitroxides are stable free radicals that contain a nitroxyl group with an unpaired electron. In this paper, we present the properties and application of nitroxides as antioxidants and anticancer drugs. The mostly used nitroxides in biology and medicine are a group of heterocyclic nitroxide derivatives of piperidine, pyrroline and pyrrolidine. The antioxidant action of nitroxides is associated with their redox cycle. Nitroxides, unlike other antioxidants, are characterized by a catalytic mechanism of action associated with a single electron oxidation and reduction reaction. In biological conditions, they mimic superoxide dismutase (SOD), modulate hemoprotein’s catalase-like activity, scavenge reactive free radicals, inhibit the Fenton and Haber-Weiss reactions and suppress the oxidation of biological materials (peptides, proteins, lipids, etc.). The use of nitroxides as antioxidants against oxidative stress induced by anticancer drugs has also been investigated. The application of nitroxides and their derivatives as anticancer drugs is discussed in the contexts of breast, hepatic, lung, ovarian, lymphatic and thyroid cancers under in vivo and in vitro experiments. In this article, we focus on new natural spin-labelled derivatives such as camptothecin, rotenone, combretastatin, podophyllotoxin and others. The applications of nitroxides in the aging process, cardiovascular disease and pathological conditions were also discussed.
Highlights
Nitroxides belong to a group of stable organic radicals, containing the nitroxyl group >N–O with an unpaired electron [1]
rotenone flavonoid (Rot) interferes with the electron transport chain in mitochondria and its toxic effects could be attributed to the inhibition of mitochondrial NADH dehydrogenase in complex I [62]
The authors proposed a chemopreventive action affected by the antioxidant properties of nitroxide
Summary
Nitroxides belong to a group of stable organic radicals, containing the nitroxyl group >N–O with an unpaired electron [1]. Nitroxides inhibit oxidative stress, under certain conditions they may lead to its intensification, for example, in tumour cells This situation occurs at high nitroxide concentrations that can release iron ions that participate in the Fenton and Haber-Weiss reactions [2,5,6]. Unlike other antioxidants, they are characterised by a catalytic mechanism of action associated with a single-electron redox cycle. They are characterised by a catalytic mechanism of action associated with a single-electron redox cycle Their reduction results in the generation of hydroxylamine and oxidation in oxoammonium ion; both reactions are reversible [7]. Nhiytrdorxoigdeens hpaevroexsidheow[4n5].toNsitcraovxeindgese hRaOvSe sinhotwhen ftollsocwavinenggoerRdeOrS: ihnytdhreoxfoylllorwadinicgalosrd>ehr:yhdyrdogroexnypl erarodxicidales > shuypderroogxeindep. erToExMidPe O>Lsu(4p-ehryodxridoxe.y-T2E,2M,6P,6OtLetr(4a-mhyetdhryolxpyi-p2e,2ri,d6,i6net-e1t-roaxmyelt)hwylapsipfeoruidnidnet-o1-eofxfeycl)tivwealys sfocauvnedntgoeeofrfescutipvpelryessscafovremngaetionr soufphpyrdersosxfyorlmraadtiocanlsofinhsyideroCxuyl, Zrand-iScOalDs .inItsiadlesoCiun,aZctniv-SaOteDs .sIitnagllseot oinxaycgteivna,tpeserosixnygllaetndoxaylkgoexny, lpreardoixcayls,annidtroaglkeonxdyiloxraiddeic[a4l1s,46n,i4tr7o]gaennd dstirooxnidgeox[4id1i,z4i6n,4g7a] nadnnditsrtartoing aogxeidnitzipnegroaxnydnnitirtritaetin[4g8a–g5e1n].t pAersofxryeneitrraidteic[a4l8s–,5n1]it.rAoxsifdrees raardeicaallsso, nsictarovxeindgeesrasreofalcsaorsbcoanv-ecnengeterrseodf rcadrbicoanl-sc[e5n2t]e.reNditrraodxiicdaels [o5x2i]d. iNseittrroaxnidsieesnotxmideitsael tiroannssitehnattmtaektealpioarntsitnhatht etaFkeenptoarnt ainndthHe Faebnetro-Wn eainsds rHeacbteior-nWs,episresvrenatcitniognbsi,oplorgeviceanltminagtebriioalofgroicmalomxiadtaetriivael fdraommaogxei[d3a0t,i5v3e–5d5a]maangdee[x3h0i,b5i3t–f5e5rr]oaxnidaesxeh-liibkiet afecrtrivoixtiyd[a2s1e]-.like activity [21]
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