Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters

Autores
Costantino, Andrea Rosana; Neudörfl, Jörg M.; Ocampo, Romina Andrea; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Koll, Liliana Cristina; Mandolesi, Sandra Delia
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Background: Organotin(IV) derivatives have appeared recently as potential biologically active metallopharmaceuticals exhibiting a variety of therapeutic activities. Hence, it is important to study the synthesis of new organotin compounds with low toxicity that may be of pharmacological interest.Objectives:This study focuses on the synthesis of new bis-stannylated derivatives with C2 symmetry that could be tested as antifungal agents against two clinical important fungal species, Cryptococcus neoformans and Candida albicans.Methods:The radical addition of triorganotin hydrides (R3SnH) and diorganotin chlorohydrides (R2ClSnH) to bis-α,β-unsaturated diesters derived from (S)-BINOL led to the corresponding new bis-stannylated derivatives with C2 symmetry. Nine pure organotin compounds were synthesized with defined stereochemistry. Four of them were enantiomerically pure and four were diastereoisomeric mixtures.Results:All new organotin compounds were fully characterized, those with phenyl ligands bonded to tin were the most active compounds against both the strains (Cryptococcus neoformans and Candida albicans), with activity parameters of IC50 close to those of the reference drug (amphotericin B).Conclusion:Nine pure organotin compounds with C2 symmetry were synthesized with defined stereochemistry and their antifungal properties were tested against two clinical important fungi with IC values close to those of the reference drug. The structure-containing preferably two or three phenyl groups joined to the tin atom were highly active against both the strains compared with those possessing tri-n-butyl groups.
Fil: Costantino, Andrea Rosana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Neudörfl, Jörg M.. Universitat zu Köln; Alemania. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universitat zu Köln; Alemania
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Mandolesi, Sandra Delia. Universidad Nacional del Sur; Argentina
Materia
C2 SYMMETRY
BIS-STANNYLATED (S)-BINOL DERIVATIVES
BIS-CHLOROSTANNANES
RADICAL HYDROSTANNATION
CRYPTOCOCCUS NEOFORMANS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/99218
Acceder
id CONICETDig_a5d94606c78058d4c099826c09703fdd
oai_identifier_str oai:ri.conicet.gov.ar:11336/99218
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diestersCostantino, Andrea RosanaNeudörfl, Jörg M.Ocampo, Romina AndreaSvetaz, Laura AndreaZacchino, Susana Alicia StellaKoll, Liliana CristinaMandolesi, Sandra DeliaC2 SYMMETRYBIS-STANNYLATED (S)-BINOL DERIVATIVESBIS-CHLOROSTANNANESRADICAL HYDROSTANNATIONCRYPTOCOCCUS NEOFORMANShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Background: Organotin(IV) derivatives have appeared recently as potential biologically active metallopharmaceuticals exhibiting a variety of therapeutic activities. Hence, it is important to study the synthesis of new organotin compounds with low toxicity that may be of pharmacological interest.Objectives:This study focuses on the synthesis of new bis-stannylated derivatives with C2 symmetry that could be tested as antifungal agents against two clinical important fungal species, Cryptococcus neoformans and Candida albicans.Methods:The radical addition of triorganotin hydrides (R3SnH) and diorganotin chlorohydrides (R2ClSnH) to bis-α,β-unsaturated diesters derived from (S)-BINOL led to the corresponding new bis-stannylated derivatives with C2 symmetry. Nine pure organotin compounds were synthesized with defined stereochemistry. Four of them were enantiomerically pure and four were diastereoisomeric mixtures.Results:All new organotin compounds were fully characterized, those with phenyl ligands bonded to tin were the most active compounds against both the strains (Cryptococcus neoformans and Candida albicans), with activity parameters of IC50 close to those of the reference drug (amphotericin B).Conclusion:Nine pure organotin compounds with C2 symmetry were synthesized with defined stereochemistry and their antifungal properties were tested against two clinical important fungi with IC values close to those of the reference drug. The structure-containing preferably two or three phenyl groups joined to the tin atom were highly active against both the strains compared with those possessing tri-n-butyl groups.Fil: Costantino, Andrea Rosana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Neudörfl, Jörg M.. Universitat zu Köln; Alemania. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Zacchino, Susana Alicia Stella. Universitat zu Köln; AlemaniaFil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Mandolesi, Sandra Delia. Universidad Nacional del Sur; ArgentinaBentham Science Publishers2019-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/99218Costantino, Andrea Rosana; Neudörfl, Jörg M.; Ocampo, Romina Andrea; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; et al.; Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters; Bentham Science Publishers; Open Chemistry Journal; 6; 1; 5-2019; 34-461874-84221874-8422CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://openchemistryjournal.com/VOLUME/6/PAGE/34/info:eu-repo/semantics/altIdentifier/doi/10.2174/1874842201906010034info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:28:06Zoai:ri.conicet.gov.ar:11336/99218instacron: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 10:28:07.067CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
title Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
spellingShingle Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
Costantino, Andrea Rosana
C2 SYMMETRY
BIS-STANNYLATED (S)-BINOL DERIVATIVES
BIS-CHLOROSTANNANES
RADICAL HYDROSTANNATION
CRYPTOCOCCUS NEOFORMANS
title_short Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
title_full Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
title_fullStr Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
title_full_unstemmed Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
title_sort Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters
dc.creator.none.fl_str_mv Costantino, Andrea Rosana
Neudörfl, Jörg M.
Ocampo, Romina Andrea
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Koll, Liliana Cristina
Mandolesi, Sandra Delia
author Costantino, Andrea Rosana
author_facet Costantino, Andrea Rosana
Neudörfl, Jörg M.
Ocampo, Romina Andrea
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Koll, Liliana Cristina
Mandolesi, Sandra Delia
author_role author
author2 Neudörfl, Jörg M.
Ocampo, Romina Andrea
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Koll, Liliana Cristina
Mandolesi, Sandra Delia
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv C2 SYMMETRY
BIS-STANNYLATED (S)-BINOL DERIVATIVES
BIS-CHLOROSTANNANES
RADICAL HYDROSTANNATION
CRYPTOCOCCUS NEOFORMANS
topic C2 SYMMETRY
BIS-STANNYLATED (S)-BINOL DERIVATIVES
BIS-CHLOROSTANNANES
RADICAL HYDROSTANNATION
CRYPTOCOCCUS NEOFORMANS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Background: Organotin(IV) derivatives have appeared recently as potential biologically active metallopharmaceuticals exhibiting a variety of therapeutic activities. Hence, it is important to study the synthesis of new organotin compounds with low toxicity that may be of pharmacological interest.Objectives:This study focuses on the synthesis of new bis-stannylated derivatives with C2 symmetry that could be tested as antifungal agents against two clinical important fungal species, Cryptococcus neoformans and Candida albicans.Methods:The radical addition of triorganotin hydrides (R3SnH) and diorganotin chlorohydrides (R2ClSnH) to bis-α,β-unsaturated diesters derived from (S)-BINOL led to the corresponding new bis-stannylated derivatives with C2 symmetry. Nine pure organotin compounds were synthesized with defined stereochemistry. Four of them were enantiomerically pure and four were diastereoisomeric mixtures.Results:All new organotin compounds were fully characterized, those with phenyl ligands bonded to tin were the most active compounds against both the strains (Cryptococcus neoformans and Candida albicans), with activity parameters of IC50 close to those of the reference drug (amphotericin B).Conclusion:Nine pure organotin compounds with C2 symmetry were synthesized with defined stereochemistry and their antifungal properties were tested against two clinical important fungi with IC values close to those of the reference drug. The structure-containing preferably two or three phenyl groups joined to the tin atom were highly active against both the strains compared with those possessing tri-n-butyl groups.
Fil: Costantino, Andrea Rosana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Neudörfl, Jörg M.. Universitat zu Köln; Alemania. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universitat zu Köln; Alemania
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Mandolesi, Sandra Delia. Universidad Nacional del Sur; Argentina
description Background: Organotin(IV) derivatives have appeared recently as potential biologically active metallopharmaceuticals exhibiting a variety of therapeutic activities. Hence, it is important to study the synthesis of new organotin compounds with low toxicity that may be of pharmacological interest.Objectives:This study focuses on the synthesis of new bis-stannylated derivatives with C2 symmetry that could be tested as antifungal agents against two clinical important fungal species, Cryptococcus neoformans and Candida albicans.Methods:The radical addition of triorganotin hydrides (R3SnH) and diorganotin chlorohydrides (R2ClSnH) to bis-α,β-unsaturated diesters derived from (S)-BINOL led to the corresponding new bis-stannylated derivatives with C2 symmetry. Nine pure organotin compounds were synthesized with defined stereochemistry. Four of them were enantiomerically pure and four were diastereoisomeric mixtures.Results:All new organotin compounds were fully characterized, those with phenyl ligands bonded to tin were the most active compounds against both the strains (Cryptococcus neoformans and Candida albicans), with activity parameters of IC50 close to those of the reference drug (amphotericin B).Conclusion:Nine pure organotin compounds with C2 symmetry were synthesized with defined stereochemistry and their antifungal properties were tested against two clinical important fungi with IC values close to those of the reference drug. The structure-containing preferably two or three phenyl groups joined to the tin atom were highly active against both the strains compared with those possessing tri-n-butyl groups.
publishDate 2019
dc.date.none.fl_str_mv 2019-05
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/11336/99218
Costantino, Andrea Rosana; Neudörfl, Jörg M.; Ocampo, Romina Andrea; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; et al.; Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters; Bentham Science Publishers; Open Chemistry Journal; 6; 1; 5-2019; 34-46
1874-8422
1874-8422
CONICET Digital
CONICET
url http://hdl.handle.net/11336/99218
identifier_str_mv Costantino, Andrea Rosana; Neudörfl, Jörg M.; Ocampo, Romina Andrea; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; et al.; Synthesis, characterization and antifungal assessment of optically active bis-organotin compounds derived from (S)-BINOL diesters; Bentham Science Publishers; Open Chemistry Journal; 6; 1; 5-2019; 34-46
1874-8422
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://openchemistryjournal.com/VOLUME/6/PAGE/34/
info:eu-repo/semantics/altIdentifier/doi/10.2174/1874842201906010034
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
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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