Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

"This is the peer reviewed version of the following article: Applied Organometallic Chemistry 33.2 (2019): e4700, which has been published in final form at https://doi.org/10.1002/aoc.4700. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Us...

ver descrição completa

Detalhes bibliográficos
Autores: Huedo, Claudia, Zani, Franca, Mendiola Martín, María Antonia, Pradhan, Sayantan, Sinha, Chittaranjan, López Torres, Elena Sofía
Tipo de documento: artigo
Data de publicação:2018
País:España
Recursos:Universidad Autónoma de Madrid
Repositório:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglês
OAI Identifier:oai:repositorio.uam.es:10486/709631
Acesso em linha:http://hdl.handle.net/10486/709631
https://dx.doi.org/10.1002/aoc.4700
Access Level:Acceso aberto
Palavra-chave:Antimicrobial Activity
Hydrazones
Molecular Docking
Organotin (IV) Complexes
Thiosemicarbazones
Química
id ES_a8025e2bc532fb50a1ac0d0e984e793c
oai_identifier_str oai:repositorio.uam.es:10486/709631
network_acronym_str ES
network_name_str España
repository_id_str
spelling Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivativesHuedo, ClaudiaZani, FrancaMendiola Martín, María AntoniaPradhan, SayantanSinha, ChittaranjanLópez Torres, Elena SofíaAntimicrobial ActivityHydrazonesMolecular DockingOrganotin (IV) ComplexesThiosemicarbazonesQuímica"This is the peer reviewed version of the following article: Applied Organometallic Chemistry 33.2 (2019): e4700, which has been published in final form at https://doi.org/10.1002/aoc.4700. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions"Six organotin (IV) complexes with two ligands derived from 2,3‐butanedione and thiosemicarbazide have been synthesized and fully characterized by several spectroscopic techniques, including 119Sn NMR and single crystal X‐ray diffraction. Reactions of the ligand diacetyl‐2‐(thiosemicarbazone)‐3‐(3‐ hydroxy‐2‐naphthohydrazone), L1 H2, with SnR2Cl2 (R = Me, Bu, Ph) lead to the obtaining of complexes 1–3 with general formula [SnR2L1 ] (R = Me 1, R = Bu 2, R = Ph 3), in which the ligand is doubly deprotonated and behaves as a N2SO donor, whereas from the reactions of diacetyl‐2‐thiosemicarbazone, HATs, with the same organotin precursors any complex could be isolated. By contrast, reaction of HATs with SnR3Cl induces the ligand cyclization to form a 1,2,4‐triazine‐3‐thione that binds to the metal as a monoanionic donor in a mono or bidentate manner to form compounds 4–6 with formula [SnR3L2 ] (R = Me 4, R = Bu 5, R = Ph 6). The antimicrobial activity of the ligands and the six complexes was tested towards bacteria and fungi, including clinical isolated strains. The results show that the ligands are devoid of activity, except HATs that displays activity against Bacillus subtilis. Conversely, the complexes exhibit good antimicrobial properties against Gram positive and negative bacteria, yeasts and moulds. The best results are obtained for complexes [SnBu3L2 ] 5 and [SnPh3L2 ] 6, indicating that their more lipophilic nature could play an important role in the ease of microbial cell penetration. In some cases, these complexes display similar or higher activity than that of ampicillin and miconazole, used as antibacterial and antifungal positive controls, respectively. Docking study with DHPS protein (S. aureus) has shown that out of six drugs, the compound 6 has the best binding affinity (−8.5 Kcal/mol)Secretaría de Estado de Investigación, Desarrollo e Innovación, Grant/Award Number: CTQ2017‐90802‐REDTWileyDepartamento de Química InorgánicaFacultad de Ciencias20182018-11-26research articlehttp://purl.org/coar/resource_type/c_2df8fbb1AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/709631https://dx.doi.org/10.1002/aoc.4700reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7096312026-06-23T12:46:27Z
dc.title.none.fl_str_mv Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
title Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
spellingShingle Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
Huedo, Claudia
Antimicrobial Activity
Hydrazones
Molecular Docking
Organotin (IV) Complexes
Thiosemicarbazones
Química
title_short Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
title_full Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
title_fullStr Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
title_full_unstemmed Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
title_sort Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives
dc.creator.none.fl_str_mv Huedo, Claudia
Zani, Franca
Mendiola Martín, María Antonia
Pradhan, Sayantan
Sinha, Chittaranjan
López Torres, Elena Sofía
author Huedo, Claudia
author_facet Huedo, Claudia
Zani, Franca
Mendiola Martín, María Antonia
Pradhan, Sayantan
Sinha, Chittaranjan
López Torres, Elena Sofía
author_role author
author2 Zani, Franca
Mendiola Martín, María Antonia
Pradhan, Sayantan
Sinha, Chittaranjan
López Torres, Elena Sofía
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Inorgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Antimicrobial Activity
Hydrazones
Molecular Docking
Organotin (IV) Complexes
Thiosemicarbazones
Química
topic Antimicrobial Activity
Hydrazones
Molecular Docking
Organotin (IV) Complexes
Thiosemicarbazones
Química
description "This is the peer reviewed version of the following article: Applied Organometallic Chemistry 33.2 (2019): e4700, which has been published in final form at https://doi.org/10.1002/aoc.4700. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions"
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-11-26
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/709631
https://dx.doi.org/10.1002/aoc.4700
url http://hdl.handle.net/10486/709631
https://dx.doi.org/10.1002/aoc.4700
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869415842989473792
score 15,301603

Registros relacionados