Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives
We report here the synthesis and biological evaluation of dideoxynojirimycin and its analogs and their functional effect on glucosidase enzyme inhibition against α-glucosidase(yeast), α-galactosidase and β-galactosidase (kluyveromyces lactis). All the compounds significantly inhibited the α-glucosid...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715623002540 |
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| author | Jattuboyina Siva Krishna Hanumantharayappa Bharathkumar Saikumar Nalla Sahadev S Chirke Shalini Basetty Vyshnavi Racha Thenkrishnan Kumaraguru Ramars Amanchy Batchu Venkateswara Rao |
| author_facet | Jattuboyina Siva Krishna Hanumantharayappa Bharathkumar Saikumar Nalla Sahadev S Chirke Shalini Basetty Vyshnavi Racha Thenkrishnan Kumaraguru Ramars Amanchy Batchu Venkateswara Rao |
| author_sort | Jattuboyina Siva Krishna |
| collection | DOAJ |
| description | We report here the synthesis and biological evaluation of dideoxynojirimycin and its analogs and their functional effect on glucosidase enzyme inhibition against α-glucosidase(yeast), α-galactosidase and β-galactosidase (kluyveromyces lactis). All the compounds significantly inhibited the α-glucosidase(yeast) activity when compared to DNJ and shown strong inhibition against β-galactosidase (kluyveromyces lactis) when compared to DNJ. The molecular docking studies also reveals that these compounds showing strong ligand binding energies against yeast-ɑ-glucosidase- I, yeast β-galactosidase and human lysosomal acid–ɑ-glucosidase. Interestingly the analogues having N-H, N-alkyl and N-benzyl group along with ethyl group significantly inhibited the β-galactosidase activity when compared to DNJ. The in-silico studies are in correlation with invitro activity data; therefore, this study will be useful to develop further glycosidase inhibitors. |
| first_indexed | 2024-03-09T01:28:07Z |
| format | Article |
| id | doaj.art-2d75b26c1bad49a0ba5c8272ae165c2f |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-09T01:28:07Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-2d75b26c1bad49a0ba5c8272ae165c2f2023-12-10T06:14:54ZengElsevierResults in Chemistry2211-71562023-12-016101015Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivativesJattuboyina Siva Krishna0Hanumantharayappa Bharathkumar1Saikumar Nalla2Sahadev S Chirke3Shalini Basetty4Vyshnavi Racha5Thenkrishnan Kumaraguru6Ramars Amanchy7Batchu Venkateswara Rao8Organic Synthesis and Process Chemistry Department, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research, Ghaziabad 201002, Uttar Pradesh, IndiaOrganic Synthesis and Process Chemistry Department, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaApplied Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaOrganic Synthesis and Process Chemistry Department, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaOrganic Synthesis and Process Chemistry Department, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research, Ghaziabad 201002, Uttar Pradesh, IndiaApplied Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaOrganic Synthesis and Process Chemistry Department, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research, Ghaziabad 201002, Uttar Pradesh, IndiaApplied Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Corresponding authors.Organic Synthesis and Process Chemistry Department, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Corresponding authors.We report here the synthesis and biological evaluation of dideoxynojirimycin and its analogs and their functional effect on glucosidase enzyme inhibition against α-glucosidase(yeast), α-galactosidase and β-galactosidase (kluyveromyces lactis). All the compounds significantly inhibited the α-glucosidase(yeast) activity when compared to DNJ and shown strong inhibition against β-galactosidase (kluyveromyces lactis) when compared to DNJ. The molecular docking studies also reveals that these compounds showing strong ligand binding energies against yeast-ɑ-glucosidase- I, yeast β-galactosidase and human lysosomal acid–ɑ-glucosidase. Interestingly the analogues having N-H, N-alkyl and N-benzyl group along with ethyl group significantly inhibited the β-galactosidase activity when compared to DNJ. The in-silico studies are in correlation with invitro activity data; therefore, this study will be useful to develop further glycosidase inhibitors.http://www.sciencedirect.com/science/article/pii/S2211715623002540DideoxymethylnojirimycinGlycosidase inhibitory activityMolecular docking |
| spellingShingle | Jattuboyina Siva Krishna Hanumantharayappa Bharathkumar Saikumar Nalla Sahadev S Chirke Shalini Basetty Vyshnavi Racha Thenkrishnan Kumaraguru Ramars Amanchy Batchu Venkateswara Rao Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives Results in Chemistry Dideoxymethylnojirimycin Glycosidase inhibitory activity Molecular docking |
| title | Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives |
| title_full | Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives |
| title_fullStr | Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives |
| title_full_unstemmed | Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives |
| title_short | Synthesis, glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives |
| title_sort | synthesis glycosidase inhibitory activity and computational studies of dideoxymethylnojirimycin and its derivatives |
| topic | Dideoxymethylnojirimycin Glycosidase inhibitory activity Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2211715623002540 |
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