Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase
Background and purpose: Carbohydrate hydrolysis enzymes including α-glucosidase and α-amylase are related to type 2 diabetes mellitus. The inhibiting of these enzymes might use for type 2 diabetes mellitus treatment. Experimental approach: N-substituted-acetylpyrrolidine linked with -benzyl- (N-(ben...
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2020-01-01
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doaj-c6e8288bce224de8928fb7da6ebc2daf2021-07-07T14:31:08ZengWolters Kluwer Medknow PublicationsResearch in Pharmaceutical Sciences1735-53621735-94142020-01-01151142510.4103/1735-5362.278711Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylaseSompong SansenyaChankan WinyakulKesinee NanokWaya S PhutdhawongBackground and purpose: Carbohydrate hydrolysis enzymes including α-glucosidase and α-amylase are related to type 2 diabetes mellitus. The inhibiting of these enzymes might use for type 2 diabetes mellitus treatment. Experimental approach: N-substituted-acetylpyrrolidine linked with -benzyl- (N-(benzyl)-2-acetylpyrrolidine (4a)) and -tosyl- (N-(tosyl)-2-acetylpyrrolidine (4b)) were synthesized and evaluated for their pharmaceutical properties against a-glucosidase and a-amylase and free radical scavenging activity. The structures of 4a and 4b were determined through spectral studies (1H-NMR). Findings / Results: Both compounds 4a and 4b had highest inhibitory potential on a-glucosidase with the IC50 values of 0.52 ± 0.02 and 1.64 ± 0.08 mM, respectively. The kinetic investigation of 4a and 4b against a-glucosidase and a-amylase were functioned in mixed type inhibition. Moreover, both compounds are more likely to bind with the free enzyme than the enzyme-substrate complex based on the Ki < Ki’ on the a-glucosidase and a-amylase enzymes. Regarding the free radical scavenging, 4a had a higher capacity than 4b with IC50 values of 1.01 ± 0.010 mM for 4a and 1.82 ± 0.048 mM for 4b. Conclusion and implications: Our results indicated that a derivative of N-substitute-acetylpyrrolidine had high potential to inhibit a-glucosidase and a-amylase, and their free radical scavenging properties might be applied to the therapeutic care of patients with type 2 diabetes mellitus.http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2020;volume=15;issue=1;spage=14;epage=25;aulast=Sansenyaα-glucosidase and α-amylase inhibitory activity; diabetes type 2; type 2 diabetes mellitusn-acetylpyrrolidine. |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Sompong Sansenya Chankan Winyakul Kesinee Nanok Waya S Phutdhawong |
spellingShingle |
Sompong Sansenya Chankan Winyakul Kesinee Nanok Waya S Phutdhawong Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase Research in Pharmaceutical Sciences α-glucosidase and α-amylase inhibitory activity; diabetes type 2; type 2 diabetes mellitus n-acetylpyrrolidine. |
author_facet |
Sompong Sansenya Chankan Winyakul Kesinee Nanok Waya S Phutdhawong |
author_sort |
Sompong Sansenya |
title |
Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase |
title_short |
Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase |
title_full |
Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase |
title_fullStr |
Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase |
title_full_unstemmed |
Synthesis and inhibitory activity of N-acetylpyrrolidine derivatives on α-glucosidase and α-amylase |
title_sort |
synthesis and inhibitory activity of n-acetylpyrrolidine derivatives on α-glucosidase and α-amylase |
publisher |
Wolters Kluwer Medknow Publications |
series |
Research in Pharmaceutical Sciences |
issn |
1735-5362 1735-9414 |
publishDate |
2020-01-01 |
description |
Background and purpose: Carbohydrate hydrolysis enzymes including α-glucosidase and α-amylase are related to type 2 diabetes mellitus. The inhibiting of these enzymes might use for type 2 diabetes mellitus treatment.
Experimental approach: N-substituted-acetylpyrrolidine linked with -benzyl- (N-(benzyl)-2-acetylpyrrolidine (4a)) and -tosyl- (N-(tosyl)-2-acetylpyrrolidine (4b)) were synthesized and evaluated for their pharmaceutical properties against a-glucosidase and a-amylase and free radical scavenging activity. The structures of 4a and 4b were determined through spectral studies (1H-NMR).
Findings / Results: Both compounds 4a and 4b had highest inhibitory potential on a-glucosidase with the IC50 values of 0.52 ± 0.02 and 1.64 ± 0.08 mM, respectively. The kinetic investigation of 4a and 4b against a-glucosidase and a-amylase were functioned in mixed type inhibition. Moreover, both compounds are more likely to bind with the free enzyme than the enzyme-substrate complex based on the Ki < Ki’ on the a-glucosidase and a-amylase enzymes. Regarding the free radical scavenging, 4a had a higher capacity than 4b with IC50 values of 1.01 ± 0.010 mM for 4a and 1.82 ± 0.048 mM for 4b.
Conclusion and implications: Our results indicated that a derivative of N-substitute-acetylpyrrolidine had high potential to inhibit a-glucosidase and a-amylase, and their free radical scavenging properties might be applied to the therapeutic care of patients with type 2 diabetes mellitus. |
topic |
α-glucosidase and α-amylase inhibitory activity; diabetes type 2; type 2 diabetes mellitus n-acetylpyrrolidine. |
url |
http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2020;volume=15;issue=1;spage=14;epage=25;aulast=Sansenya |
work_keys_str_mv |
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