Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells

Detalhes bibliográficos
Autor(a) principal: Zuccolo, Marco
Data de Publicação: 2023
Outros Autores: Orsini, Giulia, Quaglia, Martina, Mirra, Luca, Corno, Cristina, Carenini, Nives, Perego, Paola, Colombo, Diego
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/165682
Resumo: Funding Information: The authors would like to acknowledge Industriale Chimica srl for funding the fellowship to M. Z. and M. Q. in memoriam of the founder Dr Fulvio Benigni as well as Associazione Italiana per la Ricerca sul Cancro (grant number 24725). The authors also thank Prof. Fiamma Ronchetti and Dr Paola Rota for the helpful discussion. Publisher Copyright: © 2023 The Royal Society of Chemistry.
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spelling Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cellsBiochemistryPhysical and Theoretical ChemistryOrganic ChemistryFunding Information: The authors would like to acknowledge Industriale Chimica srl for funding the fellowship to M. Z. and M. Q. in memoriam of the founder Dr Fulvio Benigni as well as Associazione Italiana per la Ricerca sul Cancro (grant number 24725). The authors also thank Prof. Fiamma Ronchetti and Dr Paola Rota for the helpful discussion. Publisher Copyright: © 2023 The Royal Society of Chemistry.N-Oxyamides of bioactive anionic glycoglycerolipids based on 2-O-β-d-glucosylglycerol were efficiently prepared. However, the oxidation step of the primary hydroxyl group of the glucose moiety in the presence of the N-oxyamide function appeared to be a difficult task that was nevertheless conveniently achieved for the first time by employing a chemoenzymatic laccase/TEMPO procedure. The obtained N-oxyamides exhibited a higher inhibition of proliferation of ovarian carcinoma IGROV-1 cells in serum-free medium than in complete medium, similarly to the corresponding bioactive esters. Stability and serum binding studies indicated that the observed reduced activity of the compounds in complete medium could be mainly due to a binding effect of serum proteins rather than the hydrolytic degradation of glycoglycerolipid acyl chains. Furthermore, the results of the cellular studies under serum-free conditions suggested that the N-oxyamide group could increase the antiproliferative activity of a glycoglycerolipid independently of the presence of the anionic carboxylic group. Cellular studies in other cell lines besides IGROV-1 also support a certain degree of selectivity of this series of compounds for tumor cells with Akt hyperactivation.Instituto de Tecnologia Química e Biológica António Xavier (ITQB)RUNZuccolo, MarcoOrsini, GiuliaQuaglia, MartinaMirra, LucaCorno, CristinaCarenini, NivesPerego, PaolaColombo, Diego2024-04-01T23:17:28Z2023-07-262023-07-26T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article16application/pdfhttp://hdl.handle.net/10362/165682eng1477-0520PURE: 72989603https://doi.org/10.1039/d3ob00891finfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-05-22T18:20:05Zoai:run.unl.pt:10362/165682Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-22T18:20:05Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
title Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
spellingShingle Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
Zuccolo, Marco
Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
title_short Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
title_full Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
title_fullStr Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
title_full_unstemmed Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
title_sort Synthesis of N-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
author Zuccolo, Marco
author_facet Zuccolo, Marco
Orsini, Giulia
Quaglia, Martina
Mirra, Luca
Corno, Cristina
Carenini, Nives
Perego, Paola
Colombo, Diego
author_role author
author2 Orsini, Giulia
Quaglia, Martina
Mirra, Luca
Corno, Cristina
Carenini, Nives
Perego, Paola
Colombo, Diego
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Instituto de Tecnologia Química e Biológica António Xavier (ITQB)
RUN
dc.contributor.author.fl_str_mv Zuccolo, Marco
Orsini, Giulia
Quaglia, Martina
Mirra, Luca
Corno, Cristina
Carenini, Nives
Perego, Paola
Colombo, Diego
dc.subject.por.fl_str_mv Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
topic Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
description Funding Information: The authors would like to acknowledge Industriale Chimica srl for funding the fellowship to M. Z. and M. Q. in memoriam of the founder Dr Fulvio Benigni as well as Associazione Italiana per la Ricerca sul Cancro (grant number 24725). The authors also thank Prof. Fiamma Ronchetti and Dr Paola Rota for the helpful discussion. Publisher Copyright: © 2023 The Royal Society of Chemistry.
publishDate 2023
dc.date.none.fl_str_mv 2023-07-26
2023-07-26T00:00:00Z
2024-04-01T23:17:28Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/165682
url http://hdl.handle.net/10362/165682
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1477-0520
PURE: 72989603
https://doi.org/10.1039/d3ob00891f
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 16
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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