Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate

Maria Teresa Barros; Krasimira Todorova Markova Petrova; Cláudia D. Raposo; R.C. Calheta; Marina  Sokovi􀀃; Isabel C. F.  Ferreira

doi:10.2174/1573406410666150807111029

Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate

Maria Teresa Barros, Krasimira Todorova Markova Petrova, Cláudia D. Raposo, R.C. Calheta, Marina Sokovi􀀃, Isabel C. F. Ferreira

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Abstract

Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as (1)H and (13)C 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 (GI50 357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.

Original language	English
Pages (from-to)	22-29
Number of pages	8
Journal	Journal Of Medicinal Chemistry
Volume	12
Issue number	1
Early online date	2016
DOIs	https://doi.org/10.2174/1573406410666150807111029
Publication status	Published - 2016

Keywords

Biological activity
sucrose derivatization

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@article{386e4f597b7c44fd926e804a90c64d45,

title = "Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate",

abstract = "Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as (1)H and (13)C 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 (GI50 357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.",

keywords = "Biological activity, sucrose derivatization",

author = "Barros, {Maria Teresa} and Petrova, {Krasimira Todorova Markova} and Raposo, {Cl{\'a}udia D.} and R.C. Calheta and Marina Sokovi􀀃 and Ferreira, {Isabel C. F.}",

note = "info:eu-repo/grantAgreement/FCT/3599-PPCDT/132893/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/127013/PT# Fundacao para a Ciencia e a Tecnologia PEst-OE/AGR/UI0690/2011; Serbian Ministry of Education and Science (173032) Sem pdf conforme despacho.",

year = "2016",

doi = "10.2174/1573406410666150807111029",

language = "English",

volume = "12",

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journal = "Journal Of Medicinal Chemistry",

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T1 - Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate

AU - Barros, Maria Teresa

AU - Petrova, Krasimira Todorova Markova

AU - Raposo, Cláudia D.

AU - Calheta, R.C.

AU - Sokovi􀀃, Marina

AU - Ferreira , Isabel C. F.

N1 - info:eu-repo/grantAgreement/FCT/3599-PPCDT/132893/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/127013/PT# Fundacao para a Ciencia e a Tecnologia PEst-OE/AGR/UI0690/2011; Serbian Ministry of Education and Science (173032) Sem pdf conforme despacho.

PY - 2016

Y1 - 2016

N2 - Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as (1)H and (13)C 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 (GI50 357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.

AB - Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as (1)H and (13)C 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 (GI50 357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.

KW - Biological activity

KW - sucrose derivatization

U2 - 10.2174/1573406410666150807111029

DO - 10.2174/1573406410666150807111029

M3 - Article

VL - 12

SP - 22

EP - 29

JO - Journal Of Medicinal Chemistry

JF - Journal Of Medicinal Chemistry

SN - 0022-2623

IS - 1

ER -