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Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas.
Drug Des Devel Ther 2019; 13:3485-3495DD

Abstract

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 CS2 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 H1 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 IC50 value of 62 µg/mL while alpha glucosidase by compound III with IC50 value of 75 µg/mL. The enzymes, acetylcholinesterase, and butyrylcholinesterase were potently inhibited by compound III with IC50 of 63 µg/mL and 80 µg/mL respectively. Against DPPH free radical, compound IV was more potent (IC50 = 64 µg/mL) while ABTS was more potently scavenged by compound I with IC50 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.

Authors+Show Affiliations

Department of Chemistry, University of Malakand Chakdara, Dir Lower, Kpk 18800, Pakistan.Department of Chemistry, University of Malakand Chakdara, Dir Lower, Kpk 18800, Pakistan.Department of Chemistry, University of Malakand Chakdara, Dir Lower, Kpk 18800, Pakistan.Department of Chemistry, University of Malakand Chakdara, Dir Lower, Kpk 18800, Pakistan. Department of Chemistry, GC University Faisalabad, Faisalabad, Punjab, Pakistan.Medicinal, Aromatic and Poisonous Plants Research Center (MAPRC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.Medicinal, Aromatic and Poisonous Plants Research Center (MAPRC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia. Phytochemistry Department, National Research Centre, Giza, Egypt.Department of Pharmacology, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.Department of Pharmacy, Sarhad University of Science and Information Technology, Peshawar, Kpk 25000, Pakistan.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31631973

Citation

Naz, Sumaira, et al. "Enzyme Inhibitory, Antioxidant and Antibacterial Potentials of Synthetic Symmetrical and Unsymmetrical Thioureas." Drug Design, Development and Therapy, vol. 13, 2019, pp. 3485-3495.
Naz S, Zahoor M, Umar MN, et al. Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas. Drug Des Devel Ther. 2019;13:3485-3495.
Naz, S., Zahoor, M., Umar, M. N., Ali, B., Ullah, R., Shahat, A. A., ... Sahibzada, M. U. K. (2019). Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas. Drug Design, Development and Therapy, 13, pp. 3485-3495. doi:10.2147/DDDT.S225311.
Naz S, et al. Enzyme Inhibitory, Antioxidant and Antibacterial Potentials of Synthetic Symmetrical and Unsymmetrical Thioureas. Drug Des Devel Ther. 2019;13:3485-3495. PubMed PMID: 31631973.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas. AU - Naz,Sumaira, AU - Zahoor,Muhammad, AU - Umar,Muhammad Naveed, AU - Ali,Barkat, AU - Ullah,Riaz, AU - Shahat,Abdelaaty A, AU - Mahmood,Hafiz Majid, AU - Sahibzada,Muhammad Umar Khayam, Y1 - 2019/10/07/ PY - 2019/07/30/received PY - 2019/09/10/accepted PY - 2019/10/22/entrez PY - 2019/10/22/pubmed PY - 2019/10/22/medline KW - Alzheimer’s disease KW - anti-diabetic KW - antibacterial KW - antioxidant KW - enzyme inhibition KW - picolylamine KW - symmetrical thioureas SP - 3485 EP - 3495 JF - Drug design, development and therapy JO - Drug Des Devel Ther VL - 13 N2 - 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 CS2 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 H1 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 IC50 value of 62 µg/mL while alpha glucosidase by compound III with IC50 value of 75 µg/mL. The enzymes, acetylcholinesterase, and butyrylcholinesterase were potently inhibited by compound III with IC50 of 63 µg/mL and 80 µg/mL respectively. Against DPPH free radical, compound IV was more potent (IC50 = 64 µg/mL) while ABTS was more potently scavenged by compound I with IC50 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. SN - 1177-8881 UR - https://www.unboundmedicine.com/medline/citation/31631973/Enzyme_Inhibitory,_Antioxidant_And_Antibacterial_Potentials_Of_Synthetic_Symmetrical_And_Unsymmetrical_Thioureas L2 - https://dx.doi.org/10.2147/DDDT.S225311 DB - PRIME DP - Unbound Medicine ER -