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Host−guest complexes of cyclopentadienyl iron dicarbonyl (CpFe(CO)2) CO-releasing molecules with Cucurbit[7]uril

2025-03-26Journal article Restricted access
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dc.contributor.authorMonteiro, Rodrigo P.
dc.contributor.authorCalhau, Isabel B.
dc.contributor.authorGomes, Ana C.
dc.contributor.authorMendes, Ricardo F.
dc.contributor.authorPaz, Filipe A. Almeida
dc.contributor.authorD. Lopes, André
dc.contributor.authorSilva, José Paulo da
dc.contributor.authorRomão, Carlos C.
dc.contributor.authorGonçalves, Isabel S.
dc.contributor.authorPillinger, Martyn
dc.date.accessioned2025-04-15T12:21:37Z
dc.date.available2025-04-15T12:21:37Z
dc.date.issued2025-03-26
dc.description.abstractIron(II) cyclopentadienyl carbonyl complexes are promising as CO-releasing molecules (CORMs) for therapeutic applications. In common with other metallodrugs, the practical application of Fe-CORMs may require their conjugation with biocompatible carriers to improve their bioavailability and protect them from premature degradation. Here, we show that the CO-releasing properties of the complexes [CpFe(CO)2Cl] (1) and [CpFe(CO)2CH2CONH2] (2) are retained when noncovalently encapsulated within cucurbit[7]uril (CB7), a well-established drug-enhancing excipient. The inclusion compounds were characterized in the solid-state by single-crystal and powder XRD, ATR-IR spectroscopy, Raman spectroscopy, TGA, and 13C{1H} CP MAS NMR. In the crystal structure of 2@CB7, there are two crystallographically independent [2@CB7] binary complexes that differ in the orientation of the guest molecules inside the CB cavity. High-resolution ESI-MS and 1H NMR studies verified the formation and stability of 1:1 2@CB7 inclusion complexes in an aqueous solution. In a physiological buffer, complex 2 is stable in the dark, but releases ca. 1.4 equiv of CO when irradiated with low-power cold white light, with a half-life (t 1/2) of 19.2 +/- 1.9 min. The photodecarbonylation behavior of the complexes is largely maintained in the inclusion compounds, with t 1/2 of 10.0 +/- 0.6 and 21.1 +/- 1.9 min for encapsulated 1 and 2.eng
dc.description.sponsorshipPT ALG-01-0145-FEDER-022121, 2021.05953.BD, CEECIND/02128/2017, CEECIND/00553/2017, 022161, POCI-01-0145-FEDER-022161
dc.identifier.doi10.1021/acs.organomet.4c00469
dc.identifier.eissn1520-6041
dc.identifier.issn0276-7333
dc.identifier.urihttp://hdl.handle.net/10400.1/27042
dc.language.isoeng
dc.peerreviewedyes
dc.publisherAmerican Chemical Society
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO – Aveiro Institute of Materials
dc.relationAlgarve Centre for Marine Sciences
dc.relationCentre for Marine and Environmental Research
dc.relationProdrugs in Combination with Nanocarriers for Controlled Delivery of Carbon Monoxide
dc.relationCICECO-Aveiro Institute of Materials
dc.relation.ispartofOrganometallics
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleHost−guest complexes of cyclopentadienyl iron dicarbonyl (CpFe(CO)2) CO-releasing molecules with Cucurbit[7]urileng
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO – Aveiro Institute of Materials
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleCentre for Marine and Environmental Research
oaire.awardTitleProdrugs in Combination with Nanocarriers for Controlled Delivery of Carbon Monoxide
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50011%2F2020/PT
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oaire.citation.endPage839
oaire.citation.issue7
oaire.citation.startPage824
oaire.citation.titleOrganometallics
oaire.citation.volume44
oaire.fundingStream6817 - DCRRNI ID
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oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamPOR_CENTRO
oaire.fundingStream6817 - DCRRNI ID
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameD. Lopes
person.familyNameSilva
person.givenNameAndré
person.givenNameJosé Paulo da
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person.identifier.ciencia-id351E-856A-0300
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