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Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas
BACKGROUND: In this study, 2 symmetrical and 3 unsymmetrical thioureas were synthesized to evaluate their antioxidant, antibacterial, antidiabetic, and anticholinesterase potentials. METHODS: The symmetrical thioureas were synthesized in aqueous media in the presence of sunlight, using amines and CS...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Dove
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6789174/ https://www.ncbi.nlm.nih.gov/pubmed/31631973 http://dx.doi.org/10.2147/DDDT.S225311 |
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author | Naz, Sumaira Zahoor, Muhammad Umar, Muhammad Naveed Ali, Barkat Ullah, Riaz Shahat, Abdelaaty A Mahmood, Hafiz Majid Sahibzada, Muhammad Umar Khayam |
author_facet | Naz, Sumaira Zahoor, Muhammad Umar, Muhammad Naveed Ali, Barkat Ullah, Riaz Shahat, Abdelaaty A Mahmood, Hafiz Majid Sahibzada, Muhammad Umar Khayam |
author_sort | Naz, Sumaira |
collection | PubMed |
description | BACKGROUND: In this study, 2 symmetrical and 3 unsymmetrical thioureas were synthesized to evaluate their antioxidant, antibacterial, antidiabetic, and anticholinesterase potentials. METHODS: The symmetrical thioureas were synthesized in aqueous media in the presence of sunlight, using amines and CS(2) as starting material. The unsymmetrical thioureas were synthesized using amines as a nucleophile to attack the phenyl isothiocyanate (electrophile). The structures of synthesized compounds were confirmed through H(1) NMR. The antioxidant potential was determined using DPPH and ABTS assays. The inhibition of glucose-6-phosphatase, alpha amylase, and alpha glucosidase by synthesized compounds was used as an indication of antidiabetic potential. Anticholinesterase potential was determined from the inhibition of acetylcholinesterase and butyrylcholinesterase by the synthesized compounds. RESULTS: The highest inhibition of glucose-6-phosphatase was shown by compound V (03.12 mg of phosphate released). Alpha amylase was most potently inhibited by compound IV with IC(50) value of 62 µg/mL while alpha glucosidase by compound III with IC(50) value of 75 µg/mL. The enzymes, acetylcholinesterase, and butyrylcholinesterase were potently inhibited by compound III with IC(50) of 63 µg/mL and 80 µg/mL respectively. Against DPPH free radical, compound IV was more potent (IC(50) = 64 µg/mL) while ABTS was more potently scavenged by compound I with IC(50) of 66 µg/mL. The antibacterial spectrum of synthesized compounds was determined against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Agrobacterium tumefaction and Proteus vulgaris). Compound I and compound II showed maximum activity against A. tumefaction with MIC values of 4.02 and 4.04 µg/mL respectively. Against P. vulgaris, compound V was more active (MIC = 8.94 µg/mL) while against S. aureus, compound IV was more potent with MIC of 4.03 µg/mL. CONCLUSION: From the results, it was concluded that these compounds could be used as antibacterial, antioxidant, and antidiabetic agents. However, further in vivo studies are needed to determine the toxicological effect of these compounds in living bodies. The compounds also have potential to treat neurodegenerative diseases. |
format | Online Article Text |
id | pubmed-6789174 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Dove |
record_format | MEDLINE/PubMed |
spelling | pubmed-67891742019-10-18 Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas Naz, Sumaira Zahoor, Muhammad Umar, Muhammad Naveed Ali, Barkat Ullah, Riaz Shahat, Abdelaaty A Mahmood, Hafiz Majid Sahibzada, Muhammad Umar Khayam Drug Des Devel Ther Original Research BACKGROUND: In this study, 2 symmetrical and 3 unsymmetrical thioureas were synthesized to evaluate their antioxidant, antibacterial, antidiabetic, and anticholinesterase potentials. METHODS: The symmetrical thioureas were synthesized in aqueous media in the presence of sunlight, using amines and CS(2) as starting material. The unsymmetrical thioureas were synthesized using amines as a nucleophile to attack the phenyl isothiocyanate (electrophile). The structures of synthesized compounds were confirmed through H(1) NMR. The antioxidant potential was determined using DPPH and ABTS assays. The inhibition of glucose-6-phosphatase, alpha amylase, and alpha glucosidase by synthesized compounds was used as an indication of antidiabetic potential. Anticholinesterase potential was determined from the inhibition of acetylcholinesterase and butyrylcholinesterase by the synthesized compounds. RESULTS: The highest inhibition of glucose-6-phosphatase was shown by compound V (03.12 mg of phosphate released). Alpha amylase was most potently inhibited by compound IV with IC(50) value of 62 µg/mL while alpha glucosidase by compound III with IC(50) value of 75 µg/mL. The enzymes, acetylcholinesterase, and butyrylcholinesterase were potently inhibited by compound III with IC(50) of 63 µg/mL and 80 µg/mL respectively. Against DPPH free radical, compound IV was more potent (IC(50) = 64 µg/mL) while ABTS was more potently scavenged by compound I with IC(50) of 66 µg/mL. The antibacterial spectrum of synthesized compounds was determined against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Agrobacterium tumefaction and Proteus vulgaris). Compound I and compound II showed maximum activity against A. tumefaction with MIC values of 4.02 and 4.04 µg/mL respectively. Against P. vulgaris, compound V was more active (MIC = 8.94 µg/mL) while against S. aureus, compound IV was more potent with MIC of 4.03 µg/mL. CONCLUSION: From the results, it was concluded that these compounds could be used as antibacterial, antioxidant, and antidiabetic agents. However, further in vivo studies are needed to determine the toxicological effect of these compounds in living bodies. The compounds also have potential to treat neurodegenerative diseases. Dove 2019-10-07 /pmc/articles/PMC6789174/ /pubmed/31631973 http://dx.doi.org/10.2147/DDDT.S225311 Text en © 2019 Naz et al. http://creativecommons.org/licenses/by-nc/3.0/ This work is published and licensed by Dove Medical Press Limited. The full terms of this license are available at https://www.dovepress.com/terms.php and incorporate the Creative Commons Attribution – Non Commercial (unported, v3.0) License (http://creativecommons.org/licenses/by-nc/3.0/). By accessing the work you hereby accept the Terms. Non-commercial uses of the work are permitted without any further permission from Dove Medical Press Limited, provided the work is properly attributed. For permission for commercial use of this work, please see paragraphs 4.2 and 5 of our Terms (https://www.dovepress.com/terms.php). |
spellingShingle | Original Research Naz, Sumaira Zahoor, Muhammad Umar, Muhammad Naveed Ali, Barkat Ullah, Riaz Shahat, Abdelaaty A Mahmood, Hafiz Majid Sahibzada, Muhammad Umar Khayam Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas |
title | Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas |
title_full | Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas |
title_fullStr | Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas |
title_full_unstemmed | Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas |
title_short | Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas |
title_sort | enzyme inhibitory, antioxidant and antibacterial potentials of synthetic symmetrical and unsymmetrical thioureas |
topic | Original Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6789174/ https://www.ncbi.nlm.nih.gov/pubmed/31631973 http://dx.doi.org/10.2147/DDDT.S225311 |
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