Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Autores
Ballatore, María Belén; Milanesio, María Elisa; Fujita, Hikaru; Lindsey, Jonathan S.; Durantini, Edgardo Néstor
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel bacteriochlorin bearing two spermine units (BCS) was synthesized from 3,13-dibromo-8,8,18,18-tetramethylbacteriochlorin (BC-Br3,13). The synthesis involved the Suzuki coupling of BC-Br3,13 to obtain a bacteriochlorin-dibenzaldehyde (BCA), which was subjected to reductive amination with spermine. The resulting bacteriochlorin BCS presents a strong near-infrared absorption band at 747 nm, emits at 750 nm with fluorescence quantum yield of 0.14, and generates singlet molecular oxygen, O2(1Δg), with a quantum yield of 0.27. Photokilling capacities mediated by BCS were evaluated in microbial cells. The viability of Staphylococcus aureus decreased 7 logs when cells were incubated with 1 μM BCS and irradiated for 15 minutes. Comparable photocytotoxic effect was obtained with Escherichia coli, when cells were treated for 30 minutes with visible light. BCS was also an effective photosensitizer to inactivate Candida albicans. In addition, this bacteriochlorin was able to eradicate bacteria at short incubation times. The structure of BCS contains eight basic amino groups that, when protonated in water, increase the binding to the cell envelope. In summary, the readily accessible bacteriochlorin BCS was highly effective at low concentrations as a broad-spectrum antimicrobial photosensitizer.
Fil: Ballatore, María Belén. 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
Fil: Milanesio, María Elisa. 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
Fil: Fujita, Hikaru. North Carolina State University; Estados Unidos
Fil: Lindsey, Jonathan S.. North Carolina State University; Estados Unidos
Fil: Durantini, Edgardo Néstor. 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. Universidad Nacional de Río Cuarto; Argentina
Materia
BACTERIA
BACTERIOCHLORIN
PHOTODYNAMIC INACTIVATION
PHOTOKILLING
PHOTOSENSITIZER
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:11336/119768
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/119768
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganismsBallatore, María BelénMilanesio, María ElisaFujita, HikaruLindsey, Jonathan S.Durantini, Edgardo NéstorBACTERIABACTERIOCHLORINPHOTODYNAMIC INACTIVATIONPHOTOKILLINGPHOTOSENSITIZERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel bacteriochlorin bearing two spermine units (BCS) was synthesized from 3,13-dibromo-8,8,18,18-tetramethylbacteriochlorin (BC-Br3,13). The synthesis involved the Suzuki coupling of BC-Br3,13 to obtain a bacteriochlorin-dibenzaldehyde (BCA), which was subjected to reductive amination with spermine. The resulting bacteriochlorin BCS presents a strong near-infrared absorption band at 747 nm, emits at 750 nm with fluorescence quantum yield of 0.14, and generates singlet molecular oxygen, O2(1Δg), with a quantum yield of 0.27. Photokilling capacities mediated by BCS were evaluated in microbial cells. The viability of Staphylococcus aureus decreased 7 logs when cells were incubated with 1 μM BCS and irradiated for 15 minutes. Comparable photocytotoxic effect was obtained with Escherichia coli, when cells were treated for 30 minutes with visible light. BCS was also an effective photosensitizer to inactivate Candida albicans. In addition, this bacteriochlorin was able to eradicate bacteria at short incubation times. The structure of BCS contains eight basic amino groups that, when protonated in water, increase the binding to the cell envelope. In summary, the readily accessible bacteriochlorin BCS was highly effective at low concentrations as a broad-spectrum antimicrobial photosensitizer.Fil: Ballatore, María Belén. 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; ArgentinaFil: Milanesio, María Elisa. 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; ArgentinaFil: Fujita, Hikaru. North Carolina State University; Estados UnidosFil: Lindsey, Jonathan S.. North Carolina State University; Estados UnidosFil: Durantini, Edgardo Néstor. 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. Universidad Nacional de Río Cuarto; ArgentinaWiley VCH Verlag2020-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119768Ballatore, María Belén; Milanesio, María Elisa; Fujita, Hikaru; Lindsey, Jonathan S.; Durantini, Edgardo Néstor; Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms; Wiley VCH Verlag; Journal Of Biophotonics; 13; 2; 2-2020; 1-121864-063X1864-0648CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/jbio.201960061info:eu-repo/semantics/altIdentifier/doi/10.1002/jbio.201960061info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:35:46Zoai:ri.conicet.gov.ar:11336/119768instacron: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:34982025-09-29 09:35:46.994CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
title Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
spellingShingle Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
Ballatore, María Belén
BACTERIA
BACTERIOCHLORIN
PHOTODYNAMIC INACTIVATION
PHOTOKILLING
PHOTOSENSITIZER
title_short Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
title_full Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
title_fullStr Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
title_full_unstemmed Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
title_sort Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms
dc.creator.none.fl_str_mv Ballatore, María Belén
Milanesio, María Elisa
Fujita, Hikaru
Lindsey, Jonathan S.
Durantini, Edgardo Néstor
author Ballatore, María Belén
author_facet Ballatore, María Belén
Milanesio, María Elisa
Fujita, Hikaru
Lindsey, Jonathan S.
Durantini, Edgardo Néstor
author_role author
author2 Milanesio, María Elisa
Fujita, Hikaru
Lindsey, Jonathan S.
Durantini, Edgardo Néstor
author2_role author
author
author
author
dc.subject.none.fl_str_mv BACTERIA
BACTERIOCHLORIN
PHOTODYNAMIC INACTIVATION
PHOTOKILLING
PHOTOSENSITIZER
topic BACTERIA
BACTERIOCHLORIN
PHOTODYNAMIC INACTIVATION
PHOTOKILLING
PHOTOSENSITIZER
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A novel bacteriochlorin bearing two spermine units (BCS) was synthesized from 3,13-dibromo-8,8,18,18-tetramethylbacteriochlorin (BC-Br3,13). The synthesis involved the Suzuki coupling of BC-Br3,13 to obtain a bacteriochlorin-dibenzaldehyde (BCA), which was subjected to reductive amination with spermine. The resulting bacteriochlorin BCS presents a strong near-infrared absorption band at 747 nm, emits at 750 nm with fluorescence quantum yield of 0.14, and generates singlet molecular oxygen, O2(1Δg), with a quantum yield of 0.27. Photokilling capacities mediated by BCS were evaluated in microbial cells. The viability of Staphylococcus aureus decreased 7 logs when cells were incubated with 1 μM BCS and irradiated for 15 minutes. Comparable photocytotoxic effect was obtained with Escherichia coli, when cells were treated for 30 minutes with visible light. BCS was also an effective photosensitizer to inactivate Candida albicans. In addition, this bacteriochlorin was able to eradicate bacteria at short incubation times. The structure of BCS contains eight basic amino groups that, when protonated in water, increase the binding to the cell envelope. In summary, the readily accessible bacteriochlorin BCS was highly effective at low concentrations as a broad-spectrum antimicrobial photosensitizer.
Fil: Ballatore, María Belén. 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
Fil: Milanesio, María Elisa. 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
Fil: Fujita, Hikaru. North Carolina State University; Estados Unidos
Fil: Lindsey, Jonathan S.. North Carolina State University; Estados Unidos
Fil: Durantini, Edgardo Néstor. 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. Universidad Nacional de Río Cuarto; Argentina
description A novel bacteriochlorin bearing two spermine units (BCS) was synthesized from 3,13-dibromo-8,8,18,18-tetramethylbacteriochlorin (BC-Br3,13). The synthesis involved the Suzuki coupling of BC-Br3,13 to obtain a bacteriochlorin-dibenzaldehyde (BCA), which was subjected to reductive amination with spermine. The resulting bacteriochlorin BCS presents a strong near-infrared absorption band at 747 nm, emits at 750 nm with fluorescence quantum yield of 0.14, and generates singlet molecular oxygen, O2(1Δg), with a quantum yield of 0.27. Photokilling capacities mediated by BCS were evaluated in microbial cells. The viability of Staphylococcus aureus decreased 7 logs when cells were incubated with 1 μM BCS and irradiated for 15 minutes. Comparable photocytotoxic effect was obtained with Escherichia coli, when cells were treated for 30 minutes with visible light. BCS was also an effective photosensitizer to inactivate Candida albicans. In addition, this bacteriochlorin was able to eradicate bacteria at short incubation times. The structure of BCS contains eight basic amino groups that, when protonated in water, increase the binding to the cell envelope. In summary, the readily accessible bacteriochlorin BCS was highly effective at low concentrations as a broad-spectrum antimicrobial photosensitizer.
publishDate 2020
dc.date.none.fl_str_mv 2020-02
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/11336/119768
Ballatore, María Belén; Milanesio, María Elisa; Fujita, Hikaru; Lindsey, Jonathan S.; Durantini, Edgardo Néstor; Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms; Wiley VCH Verlag; Journal Of Biophotonics; 13; 2; 2-2020; 1-12
1864-063X
1864-0648
CONICET Digital
CONICET
url http://hdl.handle.net/11336/119768
identifier_str_mv Ballatore, María Belén; Milanesio, María Elisa; Fujita, Hikaru; Lindsey, Jonathan S.; Durantini, Edgardo Néstor; Bacteriochlorin-bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms; Wiley VCH Verlag; Journal Of Biophotonics; 13; 2; 2-2020; 1-12
1864-063X
1864-0648
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/jbio.201960061
info:eu-repo/semantics/altIdentifier/doi/10.1002/jbio.201960061
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.070432

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