Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine
A series of N-alkylated deoxynojirimycin (DNJ) derivatives connected to a terminal tertiary amine at the alkyl chains of various lengths were prepared. These novel synthetic compounds were assessed for preliminary glucosidase inhibition and anticancer activities in vitro. Potent and selective inhibi...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Slovenian Chemical Society
2020-09-01
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| Series: | Acta Chimica Slovenica |
| Subjects: | |
| Online Access: | https://journals.matheo.si/index.php/ACSi/article/view/5778 |
| _version_ | 1818456594193580032 |
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| author | Lin Wang Zhijie Fang |
| author_facet | Lin Wang Zhijie Fang |
| author_sort | Lin Wang |
| collection | DOAJ |
| description | A series of N-alkylated deoxynojirimycin (DNJ) derivatives connected to a terminal tertiary amine at the alkyl chains of various lengths were prepared. These novel synthetic compounds were assessed for preliminary glucosidase inhibition and anticancer activities in vitro. Potent and selective inhibition was observed among them. Compound 7d (IC50 = 0.052 mM) showed improved and selective inhibitory activity against β-glucosidase compared to DNJ (IC50 = 0.65 mM). In addition, analysis of the kinetics of enzyme inhibition by using Lineweaver–Burk plots indicated that 7d inhibited β-glucosidase in a competitive manner, suggesting that 7d was expected to bind to the active site of β-glucosidase. Compounds 8b and 8c were found to be moderate and selective inhibitors of α-glucosidase. Nevertheless, none of compounds inhibited the growth of B16F10 melanoma cells. |
| first_indexed | 2024-12-14T22:29:09Z |
| format | Article |
| id | doaj.art-3e11ea59e05a48f9bc3e59f0e20f3861 |
| institution | Directory Open Access Journal |
| issn | 1318-0207 1580-3155 |
| language | English |
| last_indexed | 2024-12-14T22:29:09Z |
| publishDate | 2020-09-01 |
| publisher | Slovenian Chemical Society |
| record_format | Article |
| series | Acta Chimica Slovenica |
| spelling | doaj.art-3e11ea59e05a48f9bc3e59f0e20f38612022-12-21T22:45:16ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552020-09-0167381282110.17344/acsi.2019.5778874Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary AmineLin WangZhijie FangA series of N-alkylated deoxynojirimycin (DNJ) derivatives connected to a terminal tertiary amine at the alkyl chains of various lengths were prepared. These novel synthetic compounds were assessed for preliminary glucosidase inhibition and anticancer activities in vitro. Potent and selective inhibition was observed among them. Compound 7d (IC50 = 0.052 mM) showed improved and selective inhibitory activity against β-glucosidase compared to DNJ (IC50 = 0.65 mM). In addition, analysis of the kinetics of enzyme inhibition by using Lineweaver–Burk plots indicated that 7d inhibited β-glucosidase in a competitive manner, suggesting that 7d was expected to bind to the active site of β-glucosidase. Compounds 8b and 8c were found to be moderate and selective inhibitors of α-glucosidase. Nevertheless, none of compounds inhibited the growth of B16F10 melanoma cells.https://journals.matheo.si/index.php/ACSi/article/view/5778biological activitiesglucosidase1-deoxynojirimycinselective inhibition |
| spellingShingle | Lin Wang Zhijie Fang Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine Acta Chimica Slovenica biological activities glucosidase 1-deoxynojirimycin selective inhibition |
| title | Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine |
| title_full | Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine |
| title_fullStr | Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine |
| title_full_unstemmed | Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine |
| title_short | Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine |
| title_sort | study on the synthesis and biological activities of n alkylated deoxynojirimycin derivatives with a terminal tertiary amine |
| topic | biological activities glucosidase 1-deoxynojirimycin selective inhibition |
| url | https://journals.matheo.si/index.php/ACSi/article/view/5778 |
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