Complexes between 2,20-azobis(2methylpropionamidine) dihydrochloride (AAPH) and cucurbit[n]uril hosts modulate the yield and fate of photolytically-generated AAPH radicals

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dc.catalogadorpva
dc.contributor.authorForero Girón, Angie
dc.contributor.authorOyarzún Alfaro, Mauricio Sebastián
dc.contributor.authorDroguett Muñoz, Kevin Arturo
dc.contributor.authorFuentealba Patiño, Denis Alberto
dc.contributor.authorGutiérrez Oliva, Soledad
dc.contributor.authorHerrera Pisani, Bárbara Andrea
dc.contributor.authorToro Labbé, Alejandro
dc.contributor.authorFuentes Lemus, Eduardo Felipe
dc.contributor.authorDavies, Michael J.
dc.contributor.authorLópez Alarcón, Camilo Ignacio
dc.contributor.authorAliaga Miranda, Margarita Elly
dc.date.accessioned2025-01-03T16:58:43Z
dc.date.available2025-01-03T16:58:43Z
dc.date.issued2024
dc.description.abstractUsing theoretical and experimental tools we investigated the recognition of AAPH (2,2′-azobis(2-methylpropionamidine) dihydrochloride), a well-known water-soluble azo-compound employed as a source of peroxyl radicals, by cucurbit[6]uril (CB[6]), and cucurbit[8]uril (CB[8]). Density functional theory calculations and isothermal titration calorimetry experiments demonstrated that AAPH was not included in the cavity of CB[6], however, an exclusion complex was generated. Inclusion of AAPH in the CB[8] cavity was favored, forming stable inclusion complexes at 1 : 1 and 2 : 1 stoichiometries; AAPH@CB[8] and 2AAPH@CB[8], respectively. Radical formation upon photolytic cleavage of AAPH was examined theoretically, and by spin trapping with electron paramagnetic resonance. The radical yields detected with uncomplexed (free) AAPH and the AAPH-CB[6] (exclusion) complex were identical, whereas a marked decrease was shown for AAPH@CB[8]. Lower decreases were seen with a bimolecular (2 : 1) AAPH-CB[8] inclusion complex (2AAPH@CB[8]). This modulation was corroborated by the consumption of pyrogallol red (PGR), an oxidizable dye that does not associate with CB[6] or CB[8]. AAPH-CB[6] and 2AAPH@CB[8] did not significantly modify the initial consumption rate (Ri) of PGR, whereas AAPH@CB[8] decreased this. The oxidative consumption of free Trp, Gly-Trp and Trp-Gly by radicals derived from AAPH in the presence of CB[8] showed a dependence on the association of the targets with CB[8].
dc.description.funderFONDEQUIP
dc.description.funderANID
dc.description.funderFondecyt
dc.description.funderNovo Nordisk Foundation
dc.fechaingreso.objetodigital2025-01-03
dc.format.extent12 páginas
dc.fuente.origenORCID
dc.identifier.doi10.1039/D4RA07150F
dc.identifier.issn2046-2069
dc.identifier.scopusidSCOPUS_ID:85208570557
dc.identifier.urihttps://doi.org/10.1039/D4RA07150F
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/89502
dc.information.autorucEscuela de Química; Forero Girón, Angie; S/I; 1050653
dc.information.autorucEscuela de Química; Oyarzún Alfaro, Mauricio Sebastián; S/I; 223481
dc.information.autorucEscuela de Química; Droguett Muñoz, Kevin Arturo; S/I; 247052
dc.information.autorucEscuela de Química; Fuentealba Patiño, Denis Alberto; 0000-0003-4798-7204; 160255
dc.information.autorucEscuela de Química; Gutiérrez Oliva, Soledad; 0000-0002-3436-1985; 1004064
dc.information.autorucEscuela de Química; Herrera Pisani, Bárbara Andrea; 0000-0003-1911-4473; 4439
dc.information.autorucEscuela de Química; Toro Labbé, Alejandro; 0000-0001-9906-2153; 99827
dc.information.autorucEscuela de Química; Fuentes Lemus, Eduardo Felipe; 0000-0002-1465-8466; 186720
dc.information.autorucEscuela de Química; López Alarcón, Camilo Ignacio; S/I; 1004308
dc.information.autorucEscuela de Química; Aliaga Miranda, Margarita Elly; 0000-0002-4143-0301; 13361
dc.issue.numero48
dc.language.isoen
dc.nota.accesocontenido completo
dc.pagina.final35991
dc.pagina.inicio35980
dc.publisherRoyal Society of Chemistry
dc.revistaRSC Advances
dc.rightsacceso abierto
dc.rights.licenseCC BY-NC 3.0 Attribution-NonCommercial 3.0 Unported
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/
dc.subject.ddc510
dc.subject.deweyMatemática física y químicaes_ES
dc.subject.ods03 Good health and well-being
dc.subject.odspa03 Salud y bienestar
dc.titleComplexes between 2,20-azobis(2methylpropionamidine) dihydrochloride (AAPH) and cucurbit[n]uril hosts modulate the yield and fate of photolytically-generated AAPH radicals
dc.typeartículo
dc.volumen14
sipa.codpersvinculados1050653
sipa.codpersvinculados223481
sipa.codpersvinculados247052
sipa.codpersvinculados160255
sipa.codpersvinculados1004064
sipa.codpersvinculados4439
sipa.codpersvinculados99827
sipa.codpersvinculados186720
sipa.codpersvinculados1004308
sipa.codpersvinculados13361
sipa.trazabilidadORCID;2024-12-23
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