Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes

Bibliographic Details
Main Author: Mendoza, Johan
Publication Date: 2021
Other Authors: Cruz, Luis, de Freitas, Victor, Pina, Fernando, Basílio, Nuno
Format: Article
Language: eng
Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Download full: http://hdl.handle.net/10362/124894
Summary: Funding Information: Funding: This research was supported by the Associated Laboratory for Sustainable Chemistry, Clean Processes and Technologies LAQV through national funds from UIDB/50006/2020. FCT/MCTES is also acknowledged for supporting the National Portuguese NMR Network (ROTEIRO/0031/2013‐PINFRA/22161/2016, co‐financed by FEDER through COMPETE 2020, POCI, PORL, and FCT through PIDDAC) and for the grant PTDC/QUI‐COL/32351/2017. J.M. is grateful for the doctoral grant awarded by CONACYT (MEX/Ref. 288188). N.B. acknowledges FCT for the contract CEECIND/00466/2017.
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spelling Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenesAnthocyaninsColor stabilityHost‐guest systemsP‐Sulfonatocalix[n]arenesAnalytical ChemistryChemistry (miscellaneous)Molecular MedicinePharmaceutical ScienceDrug DiscoveryPhysical and Theoretical ChemistryOrganic ChemistryFunding Information: Funding: This research was supported by the Associated Laboratory for Sustainable Chemistry, Clean Processes and Technologies LAQV through national funds from UIDB/50006/2020. FCT/MCTES is also acknowledged for supporting the National Portuguese NMR Network (ROTEIRO/0031/2013‐PINFRA/22161/2016, co‐financed by FEDER through COMPETE 2020, POCI, PORL, and FCT through PIDDAC) and for the grant PTDC/QUI‐COL/32351/2017. J.M. is grateful for the doctoral grant awarded by CONACYT (MEX/Ref. 288188). N.B. acknowledges FCT for the contract CEECIND/00466/2017.Flavylium‐based compounds in their acidic and cationic form bring color to aqueous solutions, while under slightly acidic or neutral conditions they commonly bring discoloration. Selective host‐guest complexation between water‐soluble p‐sulfonatocalix[n]arenes (SCn) macrocycles and the flavylium cationic species can increase the stability of the colored form, expanding its domain over the pH scale. The association constants between SCn and the cationic (acid) and neutral basic forms of flavylium‐based compounds were determined through UV‐Vis host‐guest titrations at different pH values. The affinity of the hosts for synthetic chromophore was found to be higher than for a natural anthocyanin (Oenin). The higher affinity of SC4 for the synthetic flavylium was confirmed by1H NMR showing a preferential interaction of the flavylium phenyl ring with the host cavity. In contrast with its synthetic counterpart, the flavylium substitution pattern in the anthocyanin seems to limit the inclusion of the guest in the host’s binding pocket. In this case, the higher affinity was observed for the octamer (SC8) likely due to its larger cavity and higher number of negatively charged sulfonate groups.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNMendoza, JohanCruz, Luisde Freitas, VictorPina, FernandoBasílio, Nuno2021-09-21T02:07:57Z2021-09-042021-09-04T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/124894eng1420-3049PURE: 33823005https://doi.org/10.3390/molecules26175389info:eu-repo/semantics/openAccessreponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2024-05-22T17:56:14Zoai:run.unl.pt:10362/124894Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T17:27:28.655830Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
dc.title.none.fl_str_mv Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
title Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
spellingShingle Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
Mendoza, Johan
Anthocyanins
Color stability
Host‐guest systems
P‐Sulfonatocalix[n]arenes
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
title_short Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
title_full Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
title_fullStr Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
title_full_unstemmed Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
title_sort Anthocyanin color stabilization by host‐guest complexation with p‐sulfonatocalix[n]arenes
author Mendoza, Johan
author_facet Mendoza, Johan
Cruz, Luis
de Freitas, Victor
Pina, Fernando
Basílio, Nuno
author_role author
author2 Cruz, Luis
de Freitas, Victor
Pina, Fernando
Basílio, Nuno
author2_role author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Mendoza, Johan
Cruz, Luis
de Freitas, Victor
Pina, Fernando
Basílio, Nuno
dc.subject.por.fl_str_mv Anthocyanins
Color stability
Host‐guest systems
P‐Sulfonatocalix[n]arenes
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
topic Anthocyanins
Color stability
Host‐guest systems
P‐Sulfonatocalix[n]arenes
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
description Funding Information: Funding: This research was supported by the Associated Laboratory for Sustainable Chemistry, Clean Processes and Technologies LAQV through national funds from UIDB/50006/2020. FCT/MCTES is also acknowledged for supporting the National Portuguese NMR Network (ROTEIRO/0031/2013‐PINFRA/22161/2016, co‐financed by FEDER through COMPETE 2020, POCI, PORL, and FCT through PIDDAC) and for the grant PTDC/QUI‐COL/32351/2017. J.M. is grateful for the doctoral grant awarded by CONACYT (MEX/Ref. 288188). N.B. acknowledges FCT for the contract CEECIND/00466/2017.
publishDate 2021
dc.date.none.fl_str_mv 2021-09-21T02:07:57Z
2021-09-04
2021-09-04T00:00:00Z
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/10362/124894
url http://hdl.handle.net/10362/124894
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1420-3049
PURE: 33823005
https://doi.org/10.3390/molecules26175389
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
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