Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models

Detalhes bibliográficos
Autor(a) principal: Pereira, Lucas S.A. [UNESP]
Data de Publicação: 2022
Outros Autores: Camacho, Sabrina A. [UNESP], Almeida, Alexandre M. [UNESP], Gonçalves, Renato S., Caetano, Wilker, DeWolf, Christine, Aoki, Pedro H.B. [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.chemphyslip.2022.105181
http://hdl.handle.net/11449/223587
Resumo: Cell membranes are the first barriers for drug binding and key for the action of photosensitizers (PS). Herein, we report on the incorporation of the PS hypericin into Langmuir monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (DOPS) to represent eukaryotic cell membranes, and 1,2-dioleoyl-sn-glycero-3-phospho(1’-rac-glycerol) (DOPG) to mimic bacterial membranes. Surface pressure (π) vs mean molecular area (Å) isotherms showed a high degree of interaction (binding, penetration and relative solubilization) of hypericin into DPPC and DOPC monolayers. On the other hand, electrostatic repulsions govern the interactions with DOPG and DOPS, favoring hypericin self-aggregation, as visualized by Brewster angle microscopy (BAM). Indeed, the larger domains in BAM were consistent with the greater expansion of DOPG monolayers with incorporated hypericin, owing to stronger electrostatic repulsions. In contrast to DPPC, light-irradiation of DOPC monolayers containing hypericin induced loss of material due to hydrocarbon chain cleavage triggered by contact-dependent reactions between triplet excited state of hypericin and chain unsaturations. The mild effects noted for both irradiated DOPS and DOPG monolayers are attributed to hypericin self-aggregation, which may have decreased the singlet oxygen quantum yield (Φ1O2) via self-quenching, despite the increased instability induced in the monolayers.
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spelling Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane modelsHypercin incorporationPhospholipid biomembrane modelsPhotodynamic therapyPhotooxidationCell membranes are the first barriers for drug binding and key for the action of photosensitizers (PS). Herein, we report on the incorporation of the PS hypericin into Langmuir monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (DOPS) to represent eukaryotic cell membranes, and 1,2-dioleoyl-sn-glycero-3-phospho(1’-rac-glycerol) (DOPG) to mimic bacterial membranes. Surface pressure (π) vs mean molecular area (Å) isotherms showed a high degree of interaction (binding, penetration and relative solubilization) of hypericin into DPPC and DOPC monolayers. On the other hand, electrostatic repulsions govern the interactions with DOPG and DOPS, favoring hypericin self-aggregation, as visualized by Brewster angle microscopy (BAM). Indeed, the larger domains in BAM were consistent with the greater expansion of DOPG monolayers with incorporated hypericin, owing to stronger electrostatic repulsions. In contrast to DPPC, light-irradiation of DOPC monolayers containing hypericin induced loss of material due to hydrocarbon chain cleavage triggered by contact-dependent reactions between triplet excited state of hypericin and chain unsaturations. The mild effects noted for both irradiated DOPS and DOPG monolayers are attributed to hypericin self-aggregation, which may have decreased the singlet oxygen quantum yield (Φ1O2) via self-quenching, despite the increased instability induced in the monolayers.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Natural Sciences and Engineering Research Council of CanadaSão Paulo State University (UNESP) School of Sciences Humanities and Languages, SPSão Carlos Institute of Physics University of São Paulo (USP) CP 369, SPDepartment of Chemistry State University of Maringá, PRDepartment of Chemistry and Biochemistry and Centre for NanoScience Research Concordia UniversitySão Paulo State University (UNESP) School of Sciences Humanities and Languages, SPFAPESP: 2018/08077–6FAPESP: 2018/14692–5FAPESP: 2018/16713–0FAPESP: 2018/22214–6CNPq: 403713/2016–1Natural Sciences and Engineering Research Council of Canada: RGPIN-2019–07043Universidade Estadual Paulista (UNESP)Universidade de São Paulo (USP)State University of MaringáConcordia UniversityPereira, Lucas S.A. [UNESP]Camacho, Sabrina A. [UNESP]Almeida, Alexandre M. [UNESP]Gonçalves, Renato S.Caetano, WilkerDeWolf, ChristineAoki, Pedro H.B. [UNESP]2022-04-28T19:51:31Z2022-04-28T19:51:31Z2022-05-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.chemphyslip.2022.105181Chemistry and Physics of Lipids, v. 244.1873-29410009-3084http://hdl.handle.net/11449/22358710.1016/j.chemphyslip.2022.1051812-s2.0-85125992408Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengChemistry and Physics of Lipidsinfo:eu-repo/semantics/openAccess2022-04-28T19:51:31Zoai:repositorio.unesp.br:11449/223587Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T15:35:20.012090Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
title Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
spellingShingle Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
Pereira, Lucas S.A. [UNESP]
Hypercin incorporation
Phospholipid biomembrane models
Photodynamic therapy
Photooxidation
title_short Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
title_full Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
title_fullStr Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
title_full_unstemmed Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
title_sort Mechanisms of hypericin incorporation to explain the photooxidation outcomes in phospholipid biomembrane models
author Pereira, Lucas S.A. [UNESP]
author_facet Pereira, Lucas S.A. [UNESP]
Camacho, Sabrina A. [UNESP]
Almeida, Alexandre M. [UNESP]
Gonçalves, Renato S.
Caetano, Wilker
DeWolf, Christine
Aoki, Pedro H.B. [UNESP]
author_role author
author2 Camacho, Sabrina A. [UNESP]
Almeida, Alexandre M. [UNESP]
Gonçalves, Renato S.
Caetano, Wilker
DeWolf, Christine
Aoki, Pedro H.B. [UNESP]
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (UNESP)
Universidade de São Paulo (USP)
State University of Maringá
Concordia University
dc.contributor.author.fl_str_mv Pereira, Lucas S.A. [UNESP]
Camacho, Sabrina A. [UNESP]
Almeida, Alexandre M. [UNESP]
Gonçalves, Renato S.
Caetano, Wilker
DeWolf, Christine
Aoki, Pedro H.B. [UNESP]
dc.subject.por.fl_str_mv Hypercin incorporation
Phospholipid biomembrane models
Photodynamic therapy
Photooxidation
topic Hypercin incorporation
Phospholipid biomembrane models
Photodynamic therapy
Photooxidation
description Cell membranes are the first barriers for drug binding and key for the action of photosensitizers (PS). Herein, we report on the incorporation of the PS hypericin into Langmuir monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (DOPS) to represent eukaryotic cell membranes, and 1,2-dioleoyl-sn-glycero-3-phospho(1’-rac-glycerol) (DOPG) to mimic bacterial membranes. Surface pressure (π) vs mean molecular area (Å) isotherms showed a high degree of interaction (binding, penetration and relative solubilization) of hypericin into DPPC and DOPC monolayers. On the other hand, electrostatic repulsions govern the interactions with DOPG and DOPS, favoring hypericin self-aggregation, as visualized by Brewster angle microscopy (BAM). Indeed, the larger domains in BAM were consistent with the greater expansion of DOPG monolayers with incorporated hypericin, owing to stronger electrostatic repulsions. In contrast to DPPC, light-irradiation of DOPC monolayers containing hypericin induced loss of material due to hydrocarbon chain cleavage triggered by contact-dependent reactions between triplet excited state of hypericin and chain unsaturations. The mild effects noted for both irradiated DOPS and DOPG monolayers are attributed to hypericin self-aggregation, which may have decreased the singlet oxygen quantum yield (Φ1O2) via self-quenching, despite the increased instability induced in the monolayers.
publishDate 2022
dc.date.none.fl_str_mv 2022-04-28T19:51:31Z
2022-04-28T19:51:31Z
2022-05-01
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://dx.doi.org/10.1016/j.chemphyslip.2022.105181
Chemistry and Physics of Lipids, v. 244.
1873-2941
0009-3084
http://hdl.handle.net/11449/223587
10.1016/j.chemphyslip.2022.105181
2-s2.0-85125992408
url http://dx.doi.org/10.1016/j.chemphyslip.2022.105181
http://hdl.handle.net/11449/223587
identifier_str_mv Chemistry and Physics of Lipids, v. 244.
1873-2941
0009-3084
10.1016/j.chemphyslip.2022.105181
2-s2.0-85125992408
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Chemistry and Physics of Lipids
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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