Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies
In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) an...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Taylor & Francis Group
2021-01-01
|
| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | http://dx.doi.org/10.1080/14756366.2021.1929949 |
| _version_ | 1798016106572546048 |
|---|---|
| author | Tehreem Tahir Mirza Imran Shahzad Rukhsana Tabassum Muhammad Rafiq Muhammad Ashfaq Mubashir Hassan Katarzyna Kotwica-Mojzych Mariusz Mojzych |
| author_facet | Tehreem Tahir Mirza Imran Shahzad Rukhsana Tabassum Muhammad Rafiq Muhammad Ashfaq Mubashir Hassan Katarzyna Kotwica-Mojzych Mariusz Mojzych |
| author_sort | Tehreem Tahir |
| collection | DOAJ |
| description | In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC50 (µg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 µg/mL) compared to the reference drug acarbose (21.59 ± 1.5 µg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a non-competitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly. |
| first_indexed | 2024-04-11T15:44:21Z |
| format | Article |
| id | doaj.art-174b3db7d7284546a480af0437f9bf2f |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-04-11T15:44:21Z |
| publishDate | 2021-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-174b3db7d7284546a480af0437f9bf2f2022-12-22T04:15:37ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742021-01-013611508151910.1080/14756366.2021.19299491929949Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studiesTehreem Tahir0Mirza Imran Shahzad1Rukhsana Tabassum2Muhammad Rafiq3Muhammad Ashfaq4Mubashir Hassan5Katarzyna Kotwica-Mojzych6Mariusz Mojzych7Institute of Biochemistry, Biotechnology and Bioinformatics, Faculty of Science, The Islamia University of BahawalpurInstitute of Biochemistry, Biotechnology and Bioinformatics, Faculty of Science, The Islamia University of BahawalpurDepartment of Chemistry, Faculty of Science, The Islamia University of BahawalpurDepartment of Physiology and Biochemistry, Faculty of Bio-Sciences, Cholistan University of Veterinary and Animal SciencesDepartment of Chemistry, Faculty of Science, The Islamia University of BahawalpurInstitute of Molecular Biology & Biotechnology, The University of Lahore (Defense Road Campus)Department of Histology, Embryology and Cytophysiology, Medical University of LublinDepartment of Chemistry, Siedlce University of Natural Sciences and HumanitiesIn the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC50 (µg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 µg/mL) compared to the reference drug acarbose (21.59 ± 1.5 µg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a non-competitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.http://dx.doi.org/10.1080/14756366.2021.1929949antibacterialanti-diabeticazo derivativesmolecular dockingphenolic compounds |
| spellingShingle | Tehreem Tahir Mirza Imran Shahzad Rukhsana Tabassum Muhammad Rafiq Muhammad Ashfaq Mubashir Hassan Katarzyna Kotwica-Mojzych Mariusz Mojzych Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies Journal of Enzyme Inhibition and Medicinal Chemistry antibacterial anti-diabetic azo derivatives molecular docking phenolic compounds |
| title | Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies |
| title_full | Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies |
| title_fullStr | Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies |
| title_full_unstemmed | Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies |
| title_short | Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies |
| title_sort | diaryl azo derivatives as anti diabetic and antimicrobial agents synthesis in vitro kinetic and docking studies |
| topic | antibacterial anti-diabetic azo derivatives molecular docking phenolic compounds |
| url | http://dx.doi.org/10.1080/14756366.2021.1929949 |
| work_keys_str_mv | AT tehreemtahir diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT mirzaimranshahzad diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT rukhsanatabassum diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT muhammadrafiq diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT muhammadashfaq diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT mubashirhassan diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT katarzynakotwicamojzych diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies AT mariuszmojzych diarylazoderivativesasantidiabeticandantimicrobialagentssynthesisinvitrokineticanddockingstudies |