{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,21]],"date-time":"2026-05-21T18:06:13Z","timestamp":1779386773249,"version":"3.53.1"},"reference-count":71,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2026,5,12]],"date-time":"2026-05-12T00:00:00Z","timestamp":1778544000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>The reaction of the HS\u2022\/S\u2022\u2212 radical (pKa ~3.4), generated selectively from H2S by \u03b3-irradiated N2-flushed aqueous solutions at pH 5, with purine nucleosides (dG or dA), a 10-mer double-stranded oligodeoxynucleotide (ds-ODNs), and calf thymus (ct) DNA was investigated, under various experimental conditions. Concurrent quantification of the four purine 5\u2032,8-cyclo-2\u2032-deoxynucleosides (cPu) and two 8-oxo-7,8-dihydro-2\u2032-deoxypurines (8-oxo-Pu) by LC-MS\/MS analysis using isotopomeric internal standards was achieved. The formation of 8-oxo-Pu is several tens of times larger than cPu. Mechanistic schemes for the formation of the two product groups are proposed. Hydrogen atom abstraction from C5\u2032\u2013H by S\u2022\u2212 produces the cPu via cyclization of the C5\u2032 radical onto C8, forming a new covalent bond, C5\u2032\u2013C8. The unexpected formation of 8-oxo-Pu should be mechanistically more complex. We propose that an S\u2022\u2212 (coupled with H+) adds to the base rings, followed by the elimination of HS\u2212 to form the corresponding radical cation; subsequent reactions with H2O and radical disproportionation with another S\u2022\u2212 lead to 8-oxo-Pu. A comparison of S\u2022\u2212 with the available literature data for HO\u2022 reactivity towards ct-DNA in de-oxygenated aqueous solutions is also presented. Before the present findings, cPu lesions were attributed exclusively to HO\u2022 reactivity toward ct-DNA. The reaction of the thiyl radical (HOCH2CH2S\u2022) with ct-DNA was also investigated, yielding results similar to those of S\u2022\u2212 obtained under comparable experimental conditions. Our results contributed to a better understanding of DNA damage induced by reactive sulfur species (RSS), particularly the formation of purine lesions and the relative abundance of cPu versus 8-oxo-Pu.<\/jats:p>","DOI":"10.3390\/biom16050711","type":"journal-article","created":{"date-parts":[[2026,5,21]],"date-time":"2026-05-21T16:46:18Z","timestamp":1779381978000},"page":"711","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Biomimetic Studies on the Reactivity of Sulfur-Centered Radicals with Purine Moieties of DNA"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7163-3978","authenticated-orcid":false,"given":"Annalisa","family":"Masi","sequence":"first","affiliation":[{"name":"Istituto di Cristallografia, Consiglio Nazionale delle Ricerche, Via Salaria km 29.300, 00015 Monterotondo, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2916-8654","authenticated-orcid":false,"given":"Sebastian","family":"Barata-Vallejo","sequence":"additional","affiliation":[{"name":"Istituto per la Sintesi Organica e la Fotoreattivit\u00e0, Consiglio Nazionale delle Ricerche, 40129 Bologna, Italy"},{"name":"Departamento de Ciencias Qu\u00edmicas, Facultad de Farmacia y Bioqu\u00edmica, Universidad de Buenos Aires, Jun\u00edn 954, Buenos Aires CP 1113, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2626-2925","authenticated-orcid":false,"given":"Chryssostomos","family":"Chatgilialoglu","sequence":"additional","affiliation":[{"name":"Istituto per la Sintesi Organica e la Fotoreattivit\u00e0, Consiglio Nazionale delle Ricerche, 40129 Bologna, Italy"},{"name":"Center for Advanced Technologies, Adam Mickiewicz University, 61-614 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,5,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"813","DOI":"10.1038\/nrm2256","article-title":"ROS as signalling molecules: Mechanisms that generate specificity in ROS homeostasis","volume":"8","author":"Toledano","year":"2007","journal-title":"Nat. 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