<p> SUPPORTING INFORMATION </p><p>Cyclic peroxides as promising anticancer agents: in vitro cytotoxicity study of synthetic ozonides and tetraoxanes on human prostate cancer cell lines </p><p>Ivan A. Yaremenko,1,2 Mikhail A. Syroeshkin,1 Dmitri O. Levitsky,2,3 Fabrice Fleury,3 and Alexander O. Terent’ev. 1,2 </p><p>Table of contents 1Fabrice Fleury</p><p>[email protected]</p><p>Alexander O. Terent’ev [email protected]</p><p>Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Leninsky Prospect 47, Moscow, 119991, </p><p>Russian Federation</p><p>2 All-Russian Research Institute of Phytopathology, Bol’shie Vyazemy, Moscow region, 143050, Russian </p><p>Federation</p><p>3 UFIP CNRS UMR 6286, Mechanism and regulation of DNA repair team Université de Nantes, 2 rue de la </p><p>Houssinière, 44322, Nantes, France S1 NMR spectra of ozonides 1H NMR of 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S4 2-yl)ethanone, 2a 13C NMR of 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S5 2-yl)ethanone, 2a 1H NMR of 1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S6 2-yl)ethanone, 3a 13C NMR of 1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S7 2-yl)ethanone, 3a 1H NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S8 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b 13C NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S9 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b 1H NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S10 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b 13C NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S11 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b 1H NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S12 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с 13C NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S13 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с 1H NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S14 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c 13C NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S15 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c 1H NMR of 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S16 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d 13C NMR of 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S17 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d 1H NMR of 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S18 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d 13C NMR of 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S19 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d 1H NMR of 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S20 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e 13C NMR of 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S21 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e 1H NMR of 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S22</p><p>S2 trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e 13C NMR of 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S23 trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e NMR spectra of tetraoxanes 1H NMR of 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, S24 5a 13C NMR of 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6- S25 tetraoxabicyclo[2.2.1]heptane, 5a 1H NMR of 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b S26 13C NMR of 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b S27</p><p>S3 NMR spectra of ozonides 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2a</p><p>S4 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2a</p><p>1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3a S5 1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3a</p><p>S6 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b</p><p>S7 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b</p><p>S8 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b S9 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b</p><p>S10 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с S11 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с</p><p>S12 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c S13 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c</p><p>S14 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d S15 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d</p><p>S16 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d</p><p>S17 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d</p><p>S18 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e</p><p>S19 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e</p><p>S20 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e</p><p>S21 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e</p><p>S22 S23 NMR spectra of 1,2,4,5-tetraoxanes 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5a</p><p>S24 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5a</p><p>S25 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b</p><p>S26 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b</p><p>S27</p>