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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish
Pages (from-to)22-29
Number of pages8
JournalJournal Of Medicinal Chemistry
Volume12
Issue number1
Early online date2016
DOIs
Publication statusPublished - 2016

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Urethane
Sucrose
Cloaca
Optical Rotation
Fourier Transform Infrared Spectroscopy
Colon
Breast
Escherichia coli
Bacteria
Cell Line
ethyl isocyanate

Keywords

  • Biological activity
  • sucrose derivatization

Cite this

Barros, Maria Teresa ; Petrova, Krasimira Todorova Markova ; Raposo, Cláudia D. ; Calheta, R.C. ; Sokovi, Marina ; Ferreira , Isabel C. F. . / Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate. In: Journal Of Medicinal Chemistry. 2016 ; Vol. 12, No. 1. pp. 22-29.
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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.",
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Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate. / Barros, Maria Teresa; Petrova, Krasimira Todorova Markova; Raposo, Cláudia D.; Calheta, R.C.; Sokovi, Marina ; Ferreira , Isabel C. F. .

In: Journal Of Medicinal Chemistry, Vol. 12, No. 1, 2016, p. 22-29.

Research output: Contribution to journalArticle

TY - JOUR

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.

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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.

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KW - sucrose derivatization

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DO - 10.2174/1573406410666150807111029

M3 - Article

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