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dc.contributor.author
Bacellar, Isabel O. L.
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Oliveira, Maria Cecilia
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Dantas, Lucas S.
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Costa, Elierge B.
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Junqueira, Helena C.
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Martins, Waleska K.
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Durantini, Andres Matías
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Cosa, Gonzalo
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Di Mascio, Paolo
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Wainwright, Mark
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Miotto, Ronei
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Cordeiro, Rodrigo M.
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Miyamoto, Sayuri
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Baptista, Mauricio S.
dc.date.available
2022-08-08T11:00:57Z
dc.date.issued
2018-08
dc.identifier.citation
Bacellar, Isabel O. L.; Oliveira, Maria Cecilia; Dantas, Lucas S.; Costa, Elierge B.; Junqueira, Helena C.; et al.; Photosensitized Membrane Permeabilization Requires Contact-Dependent Reactions between Photosensitizer and Lipids; American Chemical Society; Journal of the American Chemical Society; 140; 30; 8-2018; 9606-9615
dc.identifier.issn
0002-7863
dc.identifier.uri
http://hdl.handle.net/11336/164485
dc.description.abstract
Although the general mechanisms of lipid oxidation are known, the chemical steps through which photosensitizers and light permeabilize lipid membranes are still poorly understood. Herein we characterized the products of lipid photooxidation and their effects on lipid bilayers, also giving insight into their formation pathways. Our experimental system was designed to allow two phenothiazinium-based photosensitizers (methylene blue, MB, and DO15) to deliver the same amount of singlet oxygen molecules per second to 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine liposome membranes, but with a substantial difference in terms of the extent of direct physical contact with lipid double bonds; that is, DO15 has a 27-times higher colocalization with ω-9 lipid double bonds than MB. Under this condition, DO15 permeabilizes membranes at least 1 order of magnitude more efficiently than MB, a result that was also valid for liposomes made of polyunsaturated lipids. Quantification of reaction products uncovered a mixture of phospholipid hydroperoxides, alcohols, ketones, and aldehydes. Although both photosensitizers allowed the formation of hydroperoxides, the oxidized products that require direct reactions between photosensitizer and lipids were more prevalent in liposomes oxidized by DO15. Membrane permeabilization was always connected with the presence of lipid aldehydes, which cause a substantial decrease in the Gibbs free energy barrier for water permeation. Processes depending on direct contact between photosensitizers and lipids were revealed to be essential for the progress of lipid oxidation and consequently for aldehyde formation, providing a molecular-level explanation of why membrane binding correlates so well with the cell-killing efficiency of photosensitizers.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
PHOTOSENSITIZER
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LIPIDS
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MEMBRANE PERMEABILIZATION
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Otras Ciencias Químicas
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Photosensitized Membrane Permeabilization Requires Contact-Dependent Reactions between Photosensitizer and Lipids
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-08-03T18:16:14Z
dc.identifier.eissn
1520-5126
dc.journal.volume
140
dc.journal.number
30
dc.journal.pagination
9606-9615
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington
dc.description.fil
Fil: Bacellar, Isabel O. L.. Universidade do Sao Paulo. Departamento de Bioquímica; Brasil. McGill University; Canadá
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Fil: Oliveira, Maria Cecilia. Universidad Federal do Abc; Brasil
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Fil: Dantas, Lucas S.. Universidade do Sao Paulo. Departamento de Bioquímica; Brasil
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Fil: Costa, Elierge B.. Universidad Federal do Abc; Brasil
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Fil: Junqueira, Helena C.. Universidade do Sao Paulo. Departamento de Bioquímica; Brasil
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Fil: Martins, Waleska K.. Universidade Anhanguera de São Paulo; Brasil
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Fil: Durantini, Andres Matías. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina. McGill University; Canadá
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Fil: Cosa, Gonzalo. McGill University; Canadá
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Fil: Di Mascio, Paolo. Universidade do Sao Paulo. Departamento de Bioquímica; Brasil
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Fil: Wainwright, Mark. Liverpool John Moores University; Reino Unido
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Fil: Miotto, Ronei. Universidad Federal do Abc; Brasil
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Fil: Cordeiro, Rodrigo M.. Universidad Federal do Abc; Brasil
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Fil: Miyamoto, Sayuri. Universidade do Sao Paulo. Departamento de Bioquímica; Brasil
dc.description.fil
Fil: Baptista, Mauricio S.. Universidade do Sao Paulo. Departamento de Bioquímica; Brasil
dc.journal.title
Journal of the American Chemical Society
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jacs.8b05014
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jacs.8b05014
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