Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate

Detalhes bibliográficos
Autor(a) principal: Raposo, Claudia
Data de Publicação: 2016
Outros Autores: Petrova, Krasimira T., Barros, M. Teresa, Calhelha, Ricardo C., Soković, Marina, Ferreira, Isabel C.F.R.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10198/13647
Resumo: Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as 1H and 13C NMR, FTIR, m.p., MS, and optical rotation. Its antibacterial, antifungal and cytotoxic activities were investigated. It exhibited strong inhibition against all bacteria tested, namely S. aureus (MIC 0.18±0.006), B. cereus (MIC 0.094±0.000), M. flavus (MIC 0.28±0.01), L. monocytogenes (MIC 0.18±0.006), P. aeruginosa (MIC 0.094±0.002), S. typhimurium (MIC 0.094±0.002), E. coli (MIC 0.18±0.006) and E. cloacae (MIC 0.18±0.006) and strong antifungal activity towards T. viride (MIC 0.09 ± 0.006), A. versicolor (MIC 0.18 ± 0.01), A. ochraceus (MIC 0.375 ± 0.01) and P. ochrochloron (MIC 0.375 ± 0.04). Furthermore, it showed moderate antitumor potential against human breast (GI50357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.
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spelling Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamateBiological activityAntimicrobial activityCytotoxic activityCarbamateCarbohydratesMicrowave chemistry,Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as 1H and 13C NMR, FTIR, m.p., MS, and optical rotation. Its antibacterial, antifungal and cytotoxic activities were investigated. It exhibited strong inhibition against all bacteria tested, namely S. aureus (MIC 0.18±0.006), B. cereus (MIC 0.094±0.000), M. flavus (MIC 0.28±0.01), L. monocytogenes (MIC 0.18±0.006), P. aeruginosa (MIC 0.094±0.002), S. typhimurium (MIC 0.094±0.002), E. coli (MIC 0.18±0.006) and E. cloacae (MIC 0.18±0.006) and strong antifungal activity towards T. viride (MIC 0.09 ± 0.006), A. versicolor (MIC 0.18 ± 0.01), A. ochraceus (MIC 0.375 ± 0.01) and P. ochrochloron (MIC 0.375 ± 0.04). Furthermore, it showed moderate antitumor potential against human breast (GI50357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.This work has been supported by Fundação para a Ciência e a Tecnologia through grants No. PEst- C/EQB/LA0006/2013 and PEst-OE/AGR/UI0690/2011. The authors thank to Serbian Ministry of Education and Science for financial support (grant No. 173032). The NMR spectrometers are part of The National NMR Facility, supported by Fundação para a Ciência e a Tecnologia (RECI/BBBBQB/ 0230/2012).Bentham Science PublishersBiblioteca Digital do IPBRaposo, ClaudiaPetrova, Krasimira T.Barros, M. TeresaCalhelha, Ricardo C.Soković, MarinaFerreira, Isabel C.F.R.2016-12-22T16:02:17Z20162016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/13647engRaposo, Claudia; Petrova, Krasimira T.; Barros, M. Teresa; Calhelha, Ricardo C.; Soković, Marina; Ferreira, Isabel C.F.R. (2016). Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate. Medicinal Chemistry. ISSN 1573-4064. 12:1, p. 22-291573-406410.2174/1573406410666150807111029info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-21T10:32:06Zoai:bibliotecadigital.ipb.pt:10198/13647Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:03:41.270929Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
title Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
spellingShingle Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
Raposo, Claudia
Biological activity
Antimicrobial activity
Cytotoxic activity
Carbamate
Carbohydrates
Microwave chemistry,
title_short Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
title_full Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
title_fullStr Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
title_full_unstemmed Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
title_sort Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
author Raposo, Claudia
author_facet Raposo, Claudia
Petrova, Krasimira T.
Barros, M. Teresa
Calhelha, Ricardo C.
Soković, Marina
Ferreira, Isabel C.F.R.
author_role author
author2 Petrova, Krasimira T.
Barros, M. Teresa
Calhelha, Ricardo C.
Soković, Marina
Ferreira, Isabel C.F.R.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Biblioteca Digital do IPB
dc.contributor.author.fl_str_mv Raposo, Claudia
Petrova, Krasimira T.
Barros, M. Teresa
Calhelha, Ricardo C.
Soković, Marina
Ferreira, Isabel C.F.R.
dc.subject.por.fl_str_mv Biological activity
Antimicrobial activity
Cytotoxic activity
Carbamate
Carbohydrates
Microwave chemistry,
topic Biological activity
Antimicrobial activity
Cytotoxic activity
Carbamate
Carbohydrates
Microwave chemistry,
description Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as 1H and 13C NMR, FTIR, m.p., MS, and optical rotation. Its antibacterial, antifungal and cytotoxic activities were investigated. It exhibited strong inhibition against all bacteria tested, namely S. aureus (MIC 0.18±0.006), B. cereus (MIC 0.094±0.000), M. flavus (MIC 0.28±0.01), L. monocytogenes (MIC 0.18±0.006), P. aeruginosa (MIC 0.094±0.002), S. typhimurium (MIC 0.094±0.002), E. coli (MIC 0.18±0.006) and E. cloacae (MIC 0.18±0.006) and strong antifungal activity towards T. viride (MIC 0.09 ± 0.006), A. versicolor (MIC 0.18 ± 0.01), A. ochraceus (MIC 0.375 ± 0.01) and P. ochrochloron (MIC 0.375 ± 0.04). Furthermore, it showed moderate antitumor potential against human breast (GI50357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.
publishDate 2016
dc.date.none.fl_str_mv 2016-12-22T16:02:17Z
2016
2016-01-01T00:00:00Z
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://hdl.handle.net/10198/13647
url http://hdl.handle.net/10198/13647
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Raposo, Claudia; Petrova, Krasimira T.; Barros, M. Teresa; Calhelha, Ricardo C.; Soković, Marina; Ferreira, Isabel C.F.R. (2016). Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate. Medicinal Chemistry. ISSN 1573-4064. 12:1, p. 22-29
1573-4064
10.2174/1573406410666150807111029
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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