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Synthesis, biological evaluation, and docking analysis of methyl hydroquinone and bromo methyl hydroquinone as potent cyclooxygenase (COX-1 and COX-2) inhibitors
Nursamsiara, Asnawi A.b, Kartasasmita R.E.b, Ibrahim S.b, Tjahjono D.H.b
a Department of Pharmaceutical Analysis, Sekolah Tinggi Ilmu Farmasi Makassar, Makassar, South Sulawesi, 90242, Indonesia
b School of Pharmacy, Bandung Institute of Technology, Bandung, West Java, 40132, Indonesia
[vc_row][vc_column][vc_row_inner][vc_column_inner][vc_separator css=”.vc_custom_1624529070653{padding-top: 30px !important;padding-bottom: 30px !important;}”][/vc_column_inner][/vc_row_inner][vc_row_inner layout=”boxed”][vc_column_inner width=”3/4″ css=”.vc_custom_1624695412187{border-right-width: 1px !important;border-right-color: #dddddd !important;border-right-style: solid !important;border-radius: 1px !important;}”][vc_empty_space][megatron_heading title=”Abstract” size=”size-sm” text_align=”text-left”][vc_column_text]© 2018 Nursamsiar et al.NSAIDs reduce inflammation and relieve fever and pain by blocking enzymes and proteins but may cause side effects and complications by their use. It is therefore important for any molecular modification to enhance their pharmacological properties. In the present investigation, synthesis, biological evaluation, and molecular docking were performed for both methyl hydroquinone (1) and its brominated compound (2) to evaluate their anti-inflammatory activity against cyclooxygenase protein as a model compound and the data compared with its native ligands. Bromination of methyl hydroquinone using dichloromethane as solvent gave the highest yield. In vitro COX-1/COX-2 inhibition studies showed that compound 2 was a more potent COX inhibitor than compound 1. The brominated compound (2) showed lower binding energy and RMSD values compared to methyl hydroquinone. Analysis of protein and ligand binding revealed that both 1 and 2 fitted into the active site and interacted with protein amino acid residues Tyr385 and Met522 in COX-1 and Tyr385, Ser530, Val523, Ala527, and Leu384 in COX-2. Substitution of bromine plays an important role in the anti-inflammatory activity of methyl hydroquinone.[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Author keywords” size=”size-sm” text_align=”text-left”][vc_column_text][/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Indexed keywords” size=”size-sm” text_align=”text-left”][vc_column_text]Bromination,Cyclooxygenase,Hydroquinone,Inflammation,NSAIDs[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Funding details” size=”size-sm” text_align=”text-left”][vc_column_text]This project was supported by Postdoctoral Research Grant of the Ministries of Research, Technology, and Higher Education Republic of Indonesia 2017.[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”DOI” size=”size-sm” text_align=”text-left”][vc_column_text]https://doi.org/10.7324/JAPS.2018.8703[/vc_column_text][/vc_column_inner][vc_column_inner width=”1/4″][vc_column_text]Widget Plumx[/vc_column_text][/vc_column_inner][/vc_row_inner][/vc_column][/vc_row][vc_row][vc_column][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][/vc_column][/vc_row]