Non-inclusion complexes between riboflavin and cyclodextrins

Autores
Bispo de Jesus, Marcelo; Fernandes Fraceto, Leonardo; Martini, María Florencia; Pickholz, Mónica Andrea; Veríssima Ferreira, Carmen; de Paula, Eneida
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Objectives To investigate the molecular interaction between β-cyclodextrin (βCD) or hydroxypropyl-β-cyclodextrin (HPβCD) and riboflavin (RF), and to test the anticancer potential of these formulations. Methods The physicochemical characterization of the association between RF and CDs was performed by UV-vis absorption, fluorescence, differential scanning calorimetry and NMR techniques. Molecular dynamics simulation was used to shed light on the mechanism of interaction of RF and CDs. Additionally, in-vitro cell culture tests were performed to evaluate the cytotoxicity of the RF-CD complexes against prostate cancer cells. Key findings Neither βCD nor HPβCD led to substantial changes in the physicochemical properties of RF (with the exception of solubility). Additionally, rotating frame Overhauser effect spectroscopy experiments detected no spatial correlations between hydrogens from the internal cavity of CDs and RF, while molecular dynamics simulations revealed out-of-ring RF-CD interactions. Notwithstanding, both RF-βCD and RF-HPβCD complexes were cytotoxic to PC3 prostate cancer cells. Conclusions The interaction between RF and either βCD or HPβCD, at low concentrations, seems to be made through hydrogen bonding between the flavonoid and the external rim of both CDs. Regardless of the mechanism of complexation, our findings indicate that RF-CD complexes significantly increase RF solubility and potentiate its antitumour effect.
Fil: Bispo de Jesus, Marcelo. Universidade Estadual de Campinas; Brasil
Fil: Fernandes Fraceto, Leonardo. Universidade Estadual de Campinas; Brasil
Fil: Martini, María Florencia. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Pickholz, Mónica Andrea. Universidade Estadual de Campinas; Brasil. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Veríssima Ferreira, Carmen. Universidade Estadual de Campinas; Brasil
Fil: de Paula, Eneida. Universidade Estadual de Campinas; Brasil
Materia
CYCLODEXTRIN
NMR
NON-INCLUSION COMPLEX
PROSTATE CANCER
RIBOFLAVIN
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/195901
Acceder
id CONICETDig_11d73cc8b2812289e82fbe27c4fad73d
oai_identifier_str oai:ri.conicet.gov.ar:11336/195901
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Non-inclusion complexes between riboflavin and cyclodextrinsBispo de Jesus, MarceloFernandes Fraceto, LeonardoMartini, María FlorenciaPickholz, Mónica AndreaVeríssima Ferreira, Carmende Paula, EneidaCYCLODEXTRINNMRNON-INCLUSION COMPLEXPROSTATE CANCERRIBOFLAVINhttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2Objectives To investigate the molecular interaction between β-cyclodextrin (βCD) or hydroxypropyl-β-cyclodextrin (HPβCD) and riboflavin (RF), and to test the anticancer potential of these formulations. Methods The physicochemical characterization of the association between RF and CDs was performed by UV-vis absorption, fluorescence, differential scanning calorimetry and NMR techniques. Molecular dynamics simulation was used to shed light on the mechanism of interaction of RF and CDs. Additionally, in-vitro cell culture tests were performed to evaluate the cytotoxicity of the RF-CD complexes against prostate cancer cells. Key findings Neither βCD nor HPβCD led to substantial changes in the physicochemical properties of RF (with the exception of solubility). Additionally, rotating frame Overhauser effect spectroscopy experiments detected no spatial correlations between hydrogens from the internal cavity of CDs and RF, while molecular dynamics simulations revealed out-of-ring RF-CD interactions. Notwithstanding, both RF-βCD and RF-HPβCD complexes were cytotoxic to PC3 prostate cancer cells. Conclusions The interaction between RF and either βCD or HPβCD, at low concentrations, seems to be made through hydrogen bonding between the flavonoid and the external rim of both CDs. Regardless of the mechanism of complexation, our findings indicate that RF-CD complexes significantly increase RF solubility and potentiate its antitumour effect.Fil: Bispo de Jesus, Marcelo. Universidade Estadual de Campinas; BrasilFil: Fernandes Fraceto, Leonardo. Universidade Estadual de Campinas; BrasilFil: Martini, María Florencia. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Pickholz, Mónica Andrea. Universidade Estadual de Campinas; Brasil. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Veríssima Ferreira, Carmen. Universidade Estadual de Campinas; BrasilFil: de Paula, Eneida. Universidade Estadual de Campinas; BrasilPharmaceutical Press-Royal Pharmaceutical Society Great Britian2012-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/195901Bispo de Jesus, Marcelo; Fernandes Fraceto, Leonardo; Martini, María Florencia; Pickholz, Mónica Andrea; Veríssima Ferreira, Carmen; et al.; Non-inclusion complexes between riboflavin and cyclodextrins; Pharmaceutical Press-Royal Pharmaceutical Society Great Britian; Journal of Pharmacy and Pharmacology; 64; 6; 6-2012; 832-8420022-3573CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/j.2042-7158.2012.01492.x/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1111/j.2042-7158.2012.01492.xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-01-14T12:38:36Zoai:ri.conicet.gov.ar:11336/195901instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982026-01-14 12:38:36.457CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Non-inclusion complexes between riboflavin and cyclodextrins
title Non-inclusion complexes between riboflavin and cyclodextrins
spellingShingle Non-inclusion complexes between riboflavin and cyclodextrins
Bispo de Jesus, Marcelo
CYCLODEXTRIN
NMR
NON-INCLUSION COMPLEX
PROSTATE CANCER
RIBOFLAVIN
title_short Non-inclusion complexes between riboflavin and cyclodextrins
title_full Non-inclusion complexes between riboflavin and cyclodextrins
title_fullStr Non-inclusion complexes between riboflavin and cyclodextrins
title_full_unstemmed Non-inclusion complexes between riboflavin and cyclodextrins
title_sort Non-inclusion complexes between riboflavin and cyclodextrins
dc.creator.none.fl_str_mv Bispo de Jesus, Marcelo
Fernandes Fraceto, Leonardo
Martini, María Florencia
Pickholz, Mónica Andrea
Veríssima Ferreira, Carmen
de Paula, Eneida
author Bispo de Jesus, Marcelo
author_facet Bispo de Jesus, Marcelo
Fernandes Fraceto, Leonardo
Martini, María Florencia
Pickholz, Mónica Andrea
Veríssima Ferreira, Carmen
de Paula, Eneida
author_role author
author2 Fernandes Fraceto, Leonardo
Martini, María Florencia
Pickholz, Mónica Andrea
Veríssima Ferreira, Carmen
de Paula, Eneida
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv CYCLODEXTRIN
NMR
NON-INCLUSION COMPLEX
PROSTATE CANCER
RIBOFLAVIN
topic CYCLODEXTRIN
NMR
NON-INCLUSION COMPLEX
PROSTATE CANCER
RIBOFLAVIN
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Objectives To investigate the molecular interaction between β-cyclodextrin (βCD) or hydroxypropyl-β-cyclodextrin (HPβCD) and riboflavin (RF), and to test the anticancer potential of these formulations. Methods The physicochemical characterization of the association between RF and CDs was performed by UV-vis absorption, fluorescence, differential scanning calorimetry and NMR techniques. Molecular dynamics simulation was used to shed light on the mechanism of interaction of RF and CDs. Additionally, in-vitro cell culture tests were performed to evaluate the cytotoxicity of the RF-CD complexes against prostate cancer cells. Key findings Neither βCD nor HPβCD led to substantial changes in the physicochemical properties of RF (with the exception of solubility). Additionally, rotating frame Overhauser effect spectroscopy experiments detected no spatial correlations between hydrogens from the internal cavity of CDs and RF, while molecular dynamics simulations revealed out-of-ring RF-CD interactions. Notwithstanding, both RF-βCD and RF-HPβCD complexes were cytotoxic to PC3 prostate cancer cells. Conclusions The interaction between RF and either βCD or HPβCD, at low concentrations, seems to be made through hydrogen bonding between the flavonoid and the external rim of both CDs. Regardless of the mechanism of complexation, our findings indicate that RF-CD complexes significantly increase RF solubility and potentiate its antitumour effect.
Fil: Bispo de Jesus, Marcelo. Universidade Estadual de Campinas; Brasil
Fil: Fernandes Fraceto, Leonardo. Universidade Estadual de Campinas; Brasil
Fil: Martini, María Florencia. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Pickholz, Mónica Andrea. Universidade Estadual de Campinas; Brasil. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Veríssima Ferreira, Carmen. Universidade Estadual de Campinas; Brasil
Fil: de Paula, Eneida. Universidade Estadual de Campinas; Brasil
description Objectives To investigate the molecular interaction between β-cyclodextrin (βCD) or hydroxypropyl-β-cyclodextrin (HPβCD) and riboflavin (RF), and to test the anticancer potential of these formulations. Methods The physicochemical characterization of the association between RF and CDs was performed by UV-vis absorption, fluorescence, differential scanning calorimetry and NMR techniques. Molecular dynamics simulation was used to shed light on the mechanism of interaction of RF and CDs. Additionally, in-vitro cell culture tests were performed to evaluate the cytotoxicity of the RF-CD complexes against prostate cancer cells. Key findings Neither βCD nor HPβCD led to substantial changes in the physicochemical properties of RF (with the exception of solubility). Additionally, rotating frame Overhauser effect spectroscopy experiments detected no spatial correlations between hydrogens from the internal cavity of CDs and RF, while molecular dynamics simulations revealed out-of-ring RF-CD interactions. Notwithstanding, both RF-βCD and RF-HPβCD complexes were cytotoxic to PC3 prostate cancer cells. Conclusions The interaction between RF and either βCD or HPβCD, at low concentrations, seems to be made through hydrogen bonding between the flavonoid and the external rim of both CDs. Regardless of the mechanism of complexation, our findings indicate that RF-CD complexes significantly increase RF solubility and potentiate its antitumour effect.
publishDate 2012
dc.date.none.fl_str_mv 2012-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/195901
Bispo de Jesus, Marcelo; Fernandes Fraceto, Leonardo; Martini, María Florencia; Pickholz, Mónica Andrea; Veríssima Ferreira, Carmen; et al.; Non-inclusion complexes between riboflavin and cyclodextrins; Pharmaceutical Press-Royal Pharmaceutical Society Great Britian; Journal of Pharmacy and Pharmacology; 64; 6; 6-2012; 832-842
0022-3573
CONICET Digital
CONICET
url http://hdl.handle.net/11336/195901
identifier_str_mv Bispo de Jesus, Marcelo; Fernandes Fraceto, Leonardo; Martini, María Florencia; Pickholz, Mónica Andrea; Veríssima Ferreira, Carmen; et al.; Non-inclusion complexes between riboflavin and cyclodextrins; Pharmaceutical Press-Royal Pharmaceutical Society Great Britian; Journal of Pharmacy and Pharmacology; 64; 6; 6-2012; 832-842
0022-3573
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/j.2042-7158.2012.01492.x/abstract
info:eu-repo/semantics/altIdentifier/doi/10.1111/j.2042-7158.2012.01492.x
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pharmaceutical Press-Royal Pharmaceutical Society Great Britian
publisher.none.fl_str_mv Pharmaceutical Press-Royal Pharmaceutical Society Great Britian
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.603104

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